97PathwaySphingolipid MetabolismThe sphingolipid metabolism pathway depicted here describes the synthesis of sphingolipids which include sphingomyelins, ceramides, phosphoceramides, glucosylceramides, galactosylceramides, sulfagalactosylceramides, lactosylceramides, and various other ceramides. The core of a sphingolipid is the long-chain amino alcohol called sphingosine. Amino acylation, with a long-chain fatty acid, at the 2-carbon position of sphingosine yields a ceramide. Sphingolipids are a component of all membranes but are particularly abundant in the myelin sheath. De novo sphingolipid synthesis begins at the cytoplasmic side of the ER (endoplasmic reticulum) with the formation of 3-keto-dihydrosphingosine (also known as 3-ketosphinganine) by the enzyme known as serine palmitoyltransferase (SPT). The preferred substrates for this reaction are palmitoyl-CoA and serine. Next, 3-keto-dihydrosphingosine is reduced to form dihydrosphingosine (also known as sphinganine) via the enzyme 3-ketodihydrosphingosine reductase (KDHR), which is also known as 3-ketosphinganine reductase. Dihydrosphingosine (sphinganine) is acylated by the action of several dihydroceramide synthases (CerS) to form dihydroceramide. Dihydroceramide is then desaturated in the original palmitic portion of the lipid via dihydroceramide desaturase 1 (DES1) to form ceramide. Following the conversion to ceramide, sphingosine is released via the action of ceramidase. Sphingosine can be re-converted into a ceramide by condensation with an acyl-CoA catalyzed by the various CerS enzymes. Ceramide may be phosphorylated by ceramide kinase to form ceramide-1-phosphate. Alternatively, it may be glycosylated by glucosylceramide synthase (to form a glucosylceramide) or galactosylceramide synthase (to form a galactosylceramide). Additionally, it can be converted to sphingomyelin by the addition of a phosphorylcholine headgroup by sphingomyelin synthase (SMS). Sphingomyelins are the only sphingolipids that are phospholipids. Diacylglycerol is also generated via this process. Alternately, ceramide may be broken down by a ceramidase to form sphingosine. Sphingosine may be phosphorylated to form sphingosine-1-phosphate, which may, in turn, be dephosphorylated to regenerate sphingosine. Sphingolipid catabolism allows the reversion of these metabolites to ceramide. The complex glycosphingolipids are hydrolyzed to glucosylceramide and galactosylceramide. These lipids are then hydrolyzed by beta-glucosidases and beta-galactosidases to regenerate ceramide. Similarly, sphingomyelins may be broken down by sphingomyelinase to create ceramides and phosphocholine. The only route by which sphingolipids are converted into non-sphingolipids is through sphingosine-1-phosphate lyase. This forms ethanolamine phosphate and hexadecenal.MetabolicPW000148CenterPathwayVisualizationContext16326004450#000099PathwayVisualization9197Sphingolipid MetabolismThe sphingolipid metabolism pathway depicted here describes the synthesis of sphingolipids which include sphingomyelins, ceramides, phosphoceramides, glucosylceramides, galactosylceramides, sulfagalactosylceramides, lactosylceramides, and various other ceramides. The core of a sphingolipid is the long-chain amino alcohol called sphingosine. Amino acylation, with a long-chain fatty acid, at the 2-carbon position of sphingosine yields a ceramide. Sphingolipids are a component of all membranes but are particularly abundant in the myelin sheath. De novo sphingolipid synthesis begins at the cytoplasmic side of the ER (endoplasmic reticulum) with the formation of 3-keto-dihydrosphingosine (also known as 3-ketosphinganine) by the enzyme known as serine palmitoyltransferase (SPT). The preferred substrates for this reaction are palmitoyl-CoA and serine. Next, 3-keto-dihydrosphingosine is reduced to form dihydrosphingosine (also known as sphinganine) via the enzyme 3-ketodihydrosphingosine reductase (KDHR), which is also known as 3-ketosphinganine reductase. Dihydrosphingosine (sphinganine) is acylated by the action of several dihydroceramide synthases (CerS) to form dihydroceramide. Dihydroceramide is then desaturated in the original palmitic portion of the lipid via dihydroceramide desaturase 1 (DES1) to form ceramide. Following the conversion to ceramide, sphingosine is released via the action of ceramidase. Sphingosine can be re-converted into a ceramide by condensation with an acyl-CoA catalyzed by the various CerS enzymes. Ceramide may be phosphorylated by ceramide kinase to form ceramide-1-phosphate. Alternatively, it may be glycosylated by glucosylceramide synthase (to form a glucosylceramide) or galactosylceramide synthase (to form a galactosylceramide). Additionally, it can be converted to sphingomyelin by the addition of a phosphorylcholine headgroup by sphingomyelin synthase (SMS). Sphingomyelins are the only sphingolipids that are phospholipids. Diacylglycerol is also generated via this process. Alternately, ceramide may be broken down by a ceramidase to form sphingosine. Sphingosine may be phosphorylated to form sphingosine-1-phosphate, which may, in turn, be dephosphorylated to regenerate sphingosine. Sphingolipid catabolism allows the reversion of these metabolites to ceramide. The complex glycosphingolipids are hydrolyzed to glucosylceramide and galactosylceramide. These lipids are then hydrolyzed by beta-glucosidases and beta-galactosidases to regenerate ceramide. Similarly, sphingomyelins may be broken down by sphingomyelinase to create ceramides and phosphocholine. The only route by which sphingolipids are converted into non-sphingolipids is through sphingosine-1-phosphate lyase. This forms ethanolamine phosphate and hexadecenal.Metabolic116698SubPathway261120Compound83Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.97Pathway84Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.97Pathway85Vance, D.E., and Vance, J.E. Biochemistry of lipids, lipoproteins, and membranes (4th ed.) (2002) Amsterdam; Boston: Elsevier.97Pathway1CellCL:000000010Glial cellCL:00001253NeuronCL:00005406MyocyteCL:00001875HepatocyteCL:00001824CardiomyocyteCL:00007462Platelet CL:00002338Beta cellCL:00006397Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle4Arabidopsis thaliana3702EukaryoteThale cress6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly2Bacteria2ProkaryoteBacteria24Solanum lycopersicum4081EukaryoteTomato23Pseudomonas aeruginosa287Prokaryote21Xenopus laevis8355EukaryoteAfrican clawed frog49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia419Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast2MitochondrionGO:000573914Mitochondrial Outer MembraneGO:000574112Mitochondrial Inner MembraneGO:000574310Cell MembraneGO:00058867Endoplasmic Reticulum MembraneGO:00057891CytosolGO:000582913Endoplasmic ReticulumGO:00057835CytoplasmGO:00057373Mitochondrial MatrixGO:000575931Periplasmic SpaceGO:000562011Extracellular SpaceGO:000561535ChloroplastGO:00095074PeroxisomeGO:000577725Golgi ApparatusGO:000579424Mitochondrial Intermembrane SpaceGO:000575819Sarcoplasmic ReticulumGO:001652936MembraneGO:001602032Inner MembraneGO:007025815NucleusGO:000563427Peroxisome MembraneGO:000577826Golgi Apparatus MembraneGO:00001396LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520253Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259739Mitochondrial membraneGO:00319661LiverBTO:00007597297Nervous SystemBTO:00014844Adrenal MedullaBTO:000004971828StomachBTO:0001307155263Sympathetic Nervous SystemBTO:00018329MuscleBTO:00008871411824BrainBTO:000014289165cardiocyteBTO:00015392Endothelium BTO:000039318PancreasBTO:000098825IntestineBTO:00006488Blood 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also known as palmityl CoA or CoA, palmitoyl, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Palmityl-CoA has been found throughout most human tissues, and has also been primarily detected in urine. Within the cell, palmityl-CoA is primarily located in the cytoplasm and mitochondria. In humans, palmityl-CoA is involved in cardiolipin biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) pathway, cardiolipin biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, cardiolipin biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, and cardiolipin biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) pathway. Palmityl-CoA is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/16:0/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(16:0/14:1(9Z)/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(a-25:0/i-14:0/16:0) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway. Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.1763-10-6C001541566715525PALMITYL-COA14902CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC37H66N7O17P3SInChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1MNBKLUUYKPBKDU-BBECNAHFSA-N1005.9431005.344873947FDB022562Hexadecanoyl coa;Hexadecanoyl coenzyme a;Palmitoyl coa;Palmitoyl coenzyme a;Palmitoyl-coa;Palmitoyl-coenzyme a;Palmityl-coa;Palmityl-coenzyme a;S-hexadecanoate;S-hexadecanoate coa;S-hexadecanoate coenzyme a;S-hexadecanoic acid;S-palmitoylcoenzyme a;CoA(16:0)PW_C001031COA16:0875388022890171647142090102096252291025244104695816269701997129163720116091231709129188921419525503497721913477227329778931127804533278049132785491157925733381844331907672109570638397120382108597288111103389114205390120228384120664407121356405121404123121411124122901121122914399123278119123915376123963447123970118125576480125589484126026481126028478126208299127106391127478206127480209127770388128847398140748186140764891120L-SerineHMDB0000187Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).56-45-1C00065595117115SER5736DB00133N[C@@H](CO)C(O)=OC3H7NO3InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1MTCFGRXMJLQNBG-REOHCLBHSA-N105.0926105.042593095FDB012739(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionatePW_C000120Ser344818102261745642107564310858841056011147690716370862017087202709071709172720216074383744315744416675222248357225915424912173151126251815379494233531842336315773201117808813378112132799793319485838311575239811992412212205612412213640612271813512466711812468812012531429712620929912629347912686020512777138812785650111393-DehydrosphinganineHMDB00014803-Dehydrosphinganine, also known as ketodihydrosphingosine or KDHS, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Thus, 3-dehydrosphinganine is considered to be a sphingoid base lipid molecule. 3-Dehydrosphinganine is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 3-dehydrosphinganine is primarily located in the cytoplasm, membrane (predicted from logP) and mitochondria. In humans, 3-dehydrosphinganine is involved in the globoid cell leukodystrophy pathway, the sphingolipid metabolism pathway, and the metachromatic leukodystrophy (MLD) pathway. 3-Dehydrosphinganine is also involved in a few metabolic disorders, which include the fabry disease pathway, the gaucher disease pathway, and the krabbe disease pathway. 3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2.16105-69-4C0293443985317862DEHYDROSPHINGANINE388895CCCCCCCCCCCCCCCC(=O)[C@@H](N)COC18H37NO2InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17,20H,2-16,19H2,1H3/t17-/m0/s1KBUNOSOGGAARKZ-KRWDZBQOSA-N299.4919299.282429433FDB022645(2s)-2-amino-1-hydroxyoctadecan-3-one;1-hydroxy-2-amino-3-oxo-octadecane;2-amino-1-hydroxy-3-octadecanone;3-dehydro-d-sphinganine;3-dehydrosphinganine;3-ketodihydrosphingosine;3-ketosphinganine;Kdhs;KetodihydrosphingosinePW_C0011393-DHPG209727203160788421321220571241246111181262102991277723881316Carbon dioxideHMDB0001967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-N44.009543.989829244DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO250812112044480135031864036773169520806511334316384917452255117314470528310353201115750108577110159681006026155607816164711786637107692219070171607035163706118871632057308198733321374612227530210821522582231519158249118492771190817012464226126882904262631543523318769942937712213377170132774703337773911277750129777633417807713478405356784273347894133179227130800083688067511980717135948363841132913911155491211199544061200891221201554071203644121205564141208334191209221241209914081212841251215053831227441201230114461231904501234184551234891181235563741238551361240633981253444791254602971255164811258244901258702991259314821262804801268875011270522061272775071273313881273905021407981851148Pyridoxal 5'-phosphateHMDB0001491This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.54-47-7C00018105118405PYRIDOXAL_PHOSPHATE1022DB00114CC1=NC=C(COP(O)(O)=O)C(C=O)=C1OC8H10NO6PInChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)NGVDGCNFYWLIFO-UHFFFAOYSA-N247.1419247.024573569FDB021820Apolon b6;Biosechs;Codecarboxylase;Coenzyme b6;Hairoxal;Hexermin-p;Hi-pyridoxin;Hiadelon;Himitan;Pal-p;Plp;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal p;Pyridoxal phosphate;Pyridoxal-p;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-p;Vitazechs;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphoric acid ester;Pyridoxal 5'-(dihydrogen phosphate);Pyridoxal-5'-phosphate;Pyridoxal 5'-phosphoric acid;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid;Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphate ester;Pyridoxal 5'-(dihydrogen phosphoric acid);Pyridoxal 5-phosphoric acid;Pyridoxal phosphoric acid;Pyridoxal-5'-phosphoric acidPW_C001148Pyr-5'P18232445351812214011969620111042145050145826212010215049532511154161175421103544111854551205567132558113365338570181607167205721621272222131185816112175151126233112628181268428912689290770172537703722577041293770522247752611277764341779733467797932778292345788553327886233180696135986307119912122120024124120029406120087407120817418121149423121155424122069123122076383122834119123402454123721458123727459124620447124627398125302297125402299125407479125458481125803489126224298126231495126942388126947501126996206127258506127786513127793390184SphinganineHMDB0000269Sphinganine is a blocker postlysosomal cholesterol transport by inhibition of low-density lipoprotein-induced esterification of cholesterol and cause unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested the possibility that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease. (PMID 1817037).764-22-7C00836914861656682609CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COC18H39NO2InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1OTKJDMGTUTTYMP-ZWKOTPCHSA-N301.5078301.298079497FDB0219242-amino-d-erythro-1,3-octadecanediol;C18-dihydrosphingosine;C18-dihydro-sphingosine;D-erythro-1,3-dihydroxy-2-aminooctadecane;D-erythro-2-amino-1,3-octadecanediol;D-erythro-c18-dihydrosphingosine;D-erythro-sphinganine;Dihydro-c18-sphingosine;Dihydrosphingosine;Erythro-sphinganine;Octadecasphinganine;Sphinganine;[r-(r*,s*)]-2-amino-1,3-octadecanediol;(2s,3r)-2-amino-1,3-octadecanediol;(r-(r*,s*))-2-aminooctadecane-1,3-diol;2-amino-1,3-dihydroxyoctadecane;C18-sphinganine;D18:0;SafingolPW_C000184d18:021002212310446818720416078845132122060124124610118126213299127775388146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N745.4209745.091102105FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH18581903778107965821188372160929161549468731479314479714531011157891085972147612815962713567791177068188710316371542057205160731521373452107559212759117081942258219151842122411812198118932111200622212150164122452861259622612648249423433154374632276911293771661327738533177394332774601307750411277511115776233368071211911316494120105407120425405120452122120616123121141125121275429121402124121483383123059376123086135123241447123712136123846464123961118124041398125472481125696297126214299126529495127009206127572388128101390140706168143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N743.405743.075452041FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390140709168414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N507.181506.995745159FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171407708911034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N427.2011427.029414749FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP2341348415224821380159631597831061141518219014921041821131021615824085924352727284727364628552931657236356144002344763147709150362651577520897521710053151115349112539210354461205544129557213356241085741117576410158491435856146587810758991475926151605015561111616231166649517867009468411886872160715920571872067208210722621372312117300198730321673912177410218743316374832228187225118512771190517012013281121802851326222315329308423283154239831342622322426963187702925377087132772161347730632977472333776633367803933278043350781701287821535178244353784143357849511578705331788491307892033480030368806221188065113580676119948271241132833881162041091199441221199944061201564071203183821203664121212484291213941231213994331214724081218993831219764101220641251220854051224054221224454351229733991230134461238184641239534471239584681240303741244523981245294441246151361246363761249474721249753751250124701253342971253734791254922991255174811256454841261254851262193001262354951262424781265504911265974991269155011277335161277803951277973901278032091281225081281685171283133891070Sphinganine 1-phosphateHMDB0001383Sphinganine 1-phosphate is an intermediate in the metabolism of Glycosphingolipids and sphingolipids. It is a substrate for Sphingosine kinase 1, Lipid phosphate phosphohydrolase 2, Sphingosine kinase 2, Sphingosine-1-phosphate lyase 1, Lipid phosphate phosphohydrolase 1 and Lipid phosphate phosphohydrolase 3.19794-97-9C0112064426016893CPD-649559277CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP(O)(O)=OC18H40NO5PInChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1YHEDRJPUIRMZMP-ZWKOTPCHSA-N381.4877381.264409907FDB0225942-amino-3-hydroxyoctadecyl dihydrogen phosphate;Dihydrosphingosine 1-phosphate;Dihydrosphingosine-1-phosphate;Sphinganine 1-phosphate;(2s,3r)-2-amino-3-hydroxyoctadecyl dihydrogen phosphate;(2s,3r)-2-amino-3-hydroxyoctadecyl dihydrogen phosphoric acidPW_C001070Sphg-1P21022212210720716078847132122062124124613118126217299127777388423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-N24.30523.985041898FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951407738911420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-N18.015318.010564686FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032OP(O)(O)=OH3O4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)NBIIXXVUZAFLBC-UHFFFAOYSA-N97.995297.976895096DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi2448488145818188312980317631417674925001027294727374631292931667236366138512342492244753150312751587520797521610053171115351112538110354471205543129557313356051355625108569365848143585514659111475941151604015561001616294107648717866911016714117684218868891607161205718920672122117306198738921074022127436163747522281962258258227101182411013425711748132117611151177321311904170119271641201428112728290132632233481917422553044235031542435318436923227701825377194293772171347794033677966130780483327805732978245353786693318002236889279308938313839479638411055839011064039111323594115845398116206109119982406120069122120699407121057124121216125121268429121352121121409123121423382121852405123304119123621118123786136123838464123968447123981399124405376124948472125362479125446297125774481125954299126221478126594300126604298126723484126904501127413388127783209128166395128177513128315389149O-PhosphoethanolamineHMDB0000224Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524, 8588821, 11566853).1071-23-4C00346101517553PHOSPHORYL-ETHANOLAMINE990NCCOP(O)(O)=OC2H8NO4PInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)SUHOOTKUPISOBE-UHFFFAOYSA-N141.063141.019094261FDB0219112-amino-ethanol dihydrogen phosphate;2-amino-ethanol dihydrogen phosphate (ester);2-amino-ethanol phosphate;2-aminoethanol o-phosphate;2-aminoethyl dihydrogen phosphate;2-aminoethyl dihydrogen phosphate (acd/name 4.0);2-aminoethyl phosphate;Colamine acid phosphate;Colamine phosphate;Colamine phosphoric acid;Colaminephosphoric acid;Colaminphosphoric acid;Eap;Ethanolamine o-phosphate;Ethanolamine acid phosphate;Ethanolamine phosphate;Mono(2-aminoethyl) phosphate;Monoaminoethyl phosphate;O-phosphocolamine;O-phosphoethanolamine;O-phosphorylethanolamine;Ope;Petn;Phosphoethanolamine;Phosphonoethanolamine;Phosphoric acid 2-aminoethyl phenyl ester;Phosphoryethanolamine;Phosphorylethanolamine;Pe;Pea;Phosphoryl-ethanolamine;2-amino-ethanol dihydrogen phosphoric acid;2-aminoethyl dihydrogen phosphoric acid;2-amino-ethanol phosphoric acid;Colaminphosphate;Ethanolamine acid phosphoric acid;Ethanolamine o-phosphoric acid;Ethanolamine phosphoric acid;Mono(2-aminoethyl) phosphoric acid;Monoaminoethyl phosphoric acid;Phosphate 2-aminoethyl phenyl ester;Ethamp;O-phosphonatoethanaminiumPW_C000149Ethamp21181049788721421212179285153283081535515115376278853332799653627997713294818385948551241132743961155314001157471181220671231246184471262222981277845131193PalmitaldehydeHMDB0001551Palmitaldehyde, also known as 1-hexadecanal, belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms. Thus, palmitaldehyde is considered to be a fatty aldehyde lipid molecule. Palmitaldehyde exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Palmitaldehyde has been primarily detected in urine. Within the cell, palmitaldehyde is primarily located in the membrane (predicted from logP), endoplasmic reticulum and cytoplasm. In humans, palmitaldehyde is involved in the globoid cell leukodystrophy pathway, the metachromatic leukodystrophy (MLD) pathway, and the sphingolipid metabolism pathway. Palmitaldehyde is also involved in a few metabolic disorders, which include the gaucher disease pathway, the fabry disease pathway, and the krabbe disease pathway. Outside of the human body, palmitaldehyde can be found in a number of food items such as bamboo shoots, kombu, common bean, and white lupine. This makes palmitaldehyde a potential biomarker for the consumption of these food products. Palmitaldehyde is an intermediate in the metabolism of Glycosphingolipid. It is a substrate for Sphingosine-1-phosphate lyase 1.629-80-1C0051798417600PALMITALDEHYDE959DB03381CCCCCCCCCCCCCCCC=OC16H32OInChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h16H,2-15H2,1H3NIOYUNMRJMEDGI-UHFFFAOYSA-N240.4247240.245315646FDB003048Palmitaldehyde;Palmitoyl aldehydePW_C001193Palmtah2119102149497215212722121378854332788613311220681231220753831246194471246263981262232981262304951277855131277923902313Ceramide (d18:1/18:0)HMDB0004950Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides.104404-17-3C00195528356572961CERAMIDE4446678CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCCC36H71NO3InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1VODZWWMEJITOND-NXCSZAMKSA-N565.9538565.543395143FDB023537(2s,3r,4e)-2-acylamino-1,3-octadec-4-enediol;(2s,3r,4e)-2-acylaminooctadec-4-ene-1,3-diol;Cer;Ceramide;N-acylsphingosine;N-[(1s,2r,3e)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide;C18 cer;Cer(d18:1/18:0);Ceramide (d18:1/18:0);N-(octadecanoyl)-sphing-4-enine;N-(octadecanoyl)ceramide;N-(octadecanoyl)sphing-4-enine;N-(stearoyl)ceramide;N-octadecanoylsphing-4-enine;N-stearoylsphing-4-enine;N-stearoylsphingosinePW_C002313Ceram182127102159497219212788583321220721231246234471262272981277895132905DihydroceramideHMDB0006752Dihydroceramide is an intermediate in sphingolipid metabolism. Dihydroceramide is the third to last step in the synthesis of beta-D-Galactosyl-1,4-beta-D glucosylceramide and is converted from sphinganine via the enzyme acyl-CoA-dependent ceramide synthase (EC 2.3.1.24). It is then converted to N-acylsphingosine via the enzyme fatty acid desaturase (EC 1.14.-.-).C12126167556243148821436314CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC=OC19H39NO3InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)18(16-21)20-17-22/h17-19,21,23H,2-16H2,1H3,(H,20,22)/t18-,19+/m0/s1XSDVOEIEBUGRQX-RBUKOAKNSA-N329.5179329.292994119FDB024056N-acylsphinganine;N-[(2s,3r)-1,3-dihydroxyoctadecan-2-yl]formamidePW_C002905DHCeram212910721821278857332122071123124622447126226298127788513188Sphingosine 1-phosphateHMDB0000277Sphingosine 1-phosphate (S1P), also known as sphing-4-enine-1-phosphate, is classified as a member of the phosphosphingolipids. Phosphosphingolipids are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. S1P is a compound with potent bioactive actions in sphingolipid metabolism, the calcium signalling pathway, and neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2) and regulates the production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets (PMID: 16219683 ). S1P is considered to be practically insoluble (in water) and acidic.26993-30-6C061245283560375504446673CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=OC18H38NO5PInChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1DUYSYHSSBDVJSM-KRWOKUGFSA-N379.4718379.248759843FDB021927(2s,3r,4e)-1-(dihydrogen phosphate)2-amino-4-octadecene-1,3-diol;C18-sphingosine 1-phosphate;D-erythro-sphingosine-1-phosphatePW_C000188S1P214849722021378860331122074383124625398126229495127791390172SphingosineHMDB0000252Sphingosine is a 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed.). Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.(Wikipedia).123-78-4C00319535395516393SPHINGOSINE4510275CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COC18H37NO2InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1WWUZIQQURGPMPG-KRWOKUGFSA-N299.4919299.282429433FDB021919(-)-d-erythro-sphingosine;(2s,3r)-sphingosine;(2s,3r,4e)-2-amino-4-octadecene-1,3-diol;(4e)-sphingenine;4-sphingenine;4-trans-sphingenine;[r-[r*,s*-(e)]]-2-amino-4-octadecene-1,3-diolPW_C000172Sphingo213617214549722421378864331122078383124629398126233495127795390353CalciumHMDB0000464Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.14127-61-8C0007627129108CA%2b2266DB01373[Ca++]CaInChI=1S/Ca/q+2BHPQYMZQTOCNFJ-UHFFFAOYSA-N40.07839.962591155FDB003513Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ionPW_C000353Ca2+276163038553146012941159932199735104631163461164471478491491421552432116582138172796182937931597131607239422941866647821048222853401115780101717920572322117258160728119011774213118371981184221012198164122152851528815115350308693361773893317760011578154132782663567852634578724130789081148041374805892288182651120220122120465405121049124121300418121377419121850383121923125122370409122895135123099376123613118123870454123936455124403398124476136124924137125571297125711478125981489126009299126050490126533495127203209127434506127460388127502507128105390140676790140677834140695503990PC(15:0/18:2(9Z,12Z))HMDB0007940PC(15:0/18:2(9Z,12Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/18:2(9Z,12Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the linoleic acid moiety is derived from seed oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.C0015724778664 PHOSPHATIDYLCHOLINE24766615CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCCC41H78NO8PInChI=1S/C41H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3,4)5)37-47-40(43)33-31-29-27-25-23-19-17-15-13-11-9-7-2/h14,16,20-21,39H,6-13,15,17-19,22-38H2,1-5H3/b16-14-,21-20-/t39-/m1/s1DGBYUHHIADYUMU-UESLNCBNSA-N744.0337743.546504989FDB0251321-pentadecanoyl-2-linoleoyl-sn-glycero-3-phosphocholine;Gpcho(15:0/18:2);Gpcho(15:0/18:2n6);Gpcho(15:0/18:2w6);Gpcho(33:2);Lecithin;Pc(15:0/18:2);Pc(15:0/18:2n6);Pc(15:0/18:2w6);Pc(33:2);Phosphatidylcholine(15:0/18:2);Phosphatidylcholine(15:0/18:2n6);Phosphatidylcholine(15:0/18:2w6);Phosphatidylcholine(33:2)PW_C003990PC15182216343723421415924491592530922369187887135689839361898403311056233861056243831166234011166243981220884191246394551262454901278075071040SM(d18:1/18:0)HMDB0001348Sphingomyelin (d18:1/18:0) or SM(d18:1/18:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/18:0) consists of oleic acid attached to the C1 position and stearic acid attached to the C2 position. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.85187-10-6C00550528358817636SPHINGO-MYELIN4446701[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCCC41H83N2O6PInChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1LKQLRGMMMAHREN-YJFXYUILSA-N731.097730.598875399FDB022570N-(octadecanoyl)-sphing-4-enine-1-phosphocholine;N-acyl-4-sphingenyl-1-o-phosphorylcholine;N-acyl-d-sphingosine-1-phosphocholine;Sphingomyelin;Sphingomyelin (d18:1/18:0)PW_C001040Sphingo2164437235214788723561220894191246404551262464901278085072928GalactosylglycerolHMDB0006790Galactosylglycerol is an intermediate in galactose and glycerolipid metabolism (KEGG: C05401). In galactose metabolism, galactosylglycerol is reversibly produced from D-galactose and glycerol by the enzyme alpha-galactosidase [EC:3.2.1.22]. It is also the first to last step in the synthesis of glycerol and is converted from 1,2-diacyl-3-beta-D-galactosyl-sn-glycerol. It is then converted to glycerol via the enzyme beta-galactosidase [EC:3.2.1.23].C0540165650415754570889OCC(O)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1OC9H18O8InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4?,5-,6+,7+,8-,9-/m1/s1NHJUPBDCSOGIKX-VGPGGAHRSA-N254.2344254.100167552FDB024079(2r,3r,4s,5r,6r)-2-[(2r)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol;3-b-d-galactosyl-sn-glycerol;3-beta-d-galactosyl-sn-glycerol;3-beta-delta-galactosyl-sn-glycerol;Azepan-2-onePW_C002928GalcGly21654330949723621477904113788733561212301261220904191238004431246414551262474901278095071202PhosphorylcholineHMDB0001565Phosphorylcholine is a small haptenic molecule, is found in a wide variety of organisms. Human hepatic tumors undergo an elevation in the concentration of phosphorylcholine as the principal metabolic change is observed (PMID: 11076016). Phosphorylcholine is the precursor metabolite of choline in the glycine, serine and threonine metabolism pathways (KEGG, map00260) and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway (KEGG, map00564).107-73-3C00588101418132PHOSPHORYL-CHOLINE989DB03945C[N+](C)(C)CCOP(O)(O)=OC5H15NO4PInChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1YHHSONZFOIEMCP-UHFFFAOYSA-O184.1507184.073869485FDB022692Choline phosphate;N-trimethyl-2-aminoethylphosphonate;O-phosphocholine;Phosphocholine;Phosphoryl-choline;Chop;Phosphorylcholine;Trimethyl(2-(phosphonooxy)ethyl)ammonium;Choline phosphoric acid;N-trimethyl-2-aminoethylphosphonic acidPW_C001202CHOP15112216743497687239214121841517853413278875356948131241132693881155261181220924191246434551259972991262494901278115076717Galactosylceramide (d18:1/18:0) HMDB0010709Galactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name "cerebroside", which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease.C026865348065324765745CCCCCCCCCCCCCCCCCC(=O)NC(CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)\C=C/CCCCCCCCCCCCCC42H81NO8InChI=1S/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29-/t35?,36?,37-,39+,40+,41-,42-/m1/s1YMYQEDCYNANIPI-JAZRPXJTSA-N728.0944727.596218573C02686Cerebroside;D-galactosyl-n-acylsphingosine;D-galactosylceramide;Gal-b-cer;Gal-beta-1-1'cer;Gal-beta-cer;Galcer;Galactocerebroside;Galactosylceramide;N-(octadecanoyl)-1-b-galactosyl-sphing-4-enine;N-(octadecanoyl)-1-beta-galactosyl-sphing-4-enine;A-galcer;Alpha-galcer;Delta-galactosyl-n-acylsphingosine;Delta-galactosylceramidePW_C006717Galacto2334Glucosylceramide (d18:1/18:0)HMDB0004972Glucosylceramide (d18:1/18:0) is a glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease.85305-87-9C011901195836484719GLUCOSYL_CERAMIDE10132611CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCCC42H81NO8InChI=1S/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+/t35-,36+,37+,39+,40-,41+,42+/m0/s1YMYQEDCYNANIPI-DYJXBSQNSA-N728.0944727.596218573FDB0235591-o-b-d-glucopyranosyl-ceramide;1-o-beta-delta-glucopyranosyl-ceramide;Ganglioside gl1a;Gaucher cerebroside;Glc-beta1->1'cer;Glcceramide;Glucocerebroside;Glucosylceramide;Beta-d-glucosyl-n-stearoylsphingosine;C18 glccer;Glccer(d18:1/18:0);N-(octadecanoyl)-1-beta-glucosyl-sphing-4-enine;B-d-glucosyl-n-stearoylsphingosine;β-d-glucosyl-n-stearoylsphingosine;B-d-glucosyl-n-octadecanoylsphingosine;β-d-glucosyl-n-octadecanoylsphingosine;N-(octadecanoyl)-1-b-glucosyl-sphing-4-enine;N-(octadecanoyl)-1-β-glucosyl-sphing-4-eninePW_C002334Glucosy193Uridine diphosphate glucoseHMDB0000286Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.133-89-1C0002953477679UDP-GLUCOSEDB01861OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1OC15H24N2O17P2InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1HSCJRCZFDFQWRP-JZMIEXBBSA-N566.3018566.055020376FDB005660(udp)glucose;(upd)-glucose;Udp glucose;Udp-d-glucose;Udp-glc;Udp-glucose;Udp-a-d-glucose;Udp-alpha-d-glucose;Udp-alpha-delta-glucose;Udp-delta-glucose;Udpg;Udpglucose;Uridine 5'-diphosphate glucose;Uridine 5'-diphospho-a-d-glucose;Uridine 5'-diphospho-alpha-d-glucose;Uridine 5'-diphospho-alpha-delta-glucose;Uridine 5'-diphosphoglucose;Uridine 5'-pyrophosphate a-d-glucopyranosyl ester;Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester;Uridine diphosphate-glucose;Uridine diphospho-d-glucose;Uridine diphospho-delta-glucose;Uridine diphosphoglucose;Uridine pyrophosphate-glucosePW_C000193UDPG112781515221964922034331182959801477245213724921472711608432151119111647792733678253132784021117888233178885356120828122121255429121363124122100383122104419123413135123825464123922118124651398124655455125819297126036299126256495126260490127272205127488388127819390127823507201Uridine 5'-diphosphateHMDB0000295Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952).58-98-0C00015603117659UDP5809DB03435O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=OC9H14N2O12P2InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1XCCTYIAWTASOJW-XVFCMESISA-N404.1612404.002196946FDB0075095'-udp;Udp;Uridine 5'-diphosphate;Uridine 5'-pyrophosphate;Uridine 5'-pyrophosphorate;Uridine 5'-pyrophosphoric acid;Uridine diphosphate;Uridine pyrophosphate;Uridine 5'-diphosphoric acid;Uridine diphosphoric acidPW_C000201UDP410815172154543219749235293115294463184518104846364946925178955527130583414170571607246213724821472872108433151119131641261522577304111773603317792433678255132782643561203151221212524291213651241213754191221013831223781251229701351238224641239241181239344551246523981249321361256432971260382991260484901262574951274903881275005071278203907187Lactosylceramide (d18:1/18:0)HMDB0011591Lactosylceramide (d18:1/18:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted. from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23).C0129010260120847598435601[H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCCC48H91NO13InChI=1S/C48H91NO13/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-59-47-45(58)43(56)46(39(34-51)61-47)62-48-44(57)42(55)41(54)38(33-50)60-48/h29,31,36-39,41-48,50-52,54-58H,3-28,30,32-35H2,1-2H3,(H,49,53)/b31-29+/t36-,37+,38+,39+,41-,42-,43+,44+,45+,46+,47+,48-/m0/s1VOZHMDQUIRUFQW-LOTHNZFDSA-N890.235889.649042003C012901-o-(4-o-b-d-galactopyranosyl-b-d-glucopyranosyl)-ceramide;1-o-(4-o-beta-d-galactopyranosyl-beta-glucopyranosyl)ceramide;1-o-(4-o-beta-delta-galactopyranosyl-beta-delta-glucopyranosyl)-ceramide;1-o-(4-o-beta-delta-galactopyranosyl-beta-glucopyranosyl)ceramide;1ylce-o-(4-o-beta-delta-galactopyranosyl-beta-glucopyranosyl)ceramide;Cdh;Cdw17 antigen;Cytolipin h;D-galactosyl-1,4-beta-d-glucosylceramide;Gal-beta1->4glc-beta1->1'cer;Laccer;Laccer(d18:1/18:0);Lactosyl ceramide (d18:1/18:0);Lactosyl-n-acylsphingosine;Lactosylceramide;N-(octadecanoyl)-1-b-lactosyl-sphing-4-enine;N-(octadecanoyl)-1-beta-lactosyl-sphing-4-enine;N-lignoceryl sphingosyl lactoside;Beta-d-galactosyl-1,4-beta-d-glucosylceramide;Beta-delta-galactosyl-1,4-beta-delta-glucosylceramide;Beta-delta-galactosyl-1,4-beta-delta-glucosramide;Delta-galactosyl-1,4-beta-delta-glucosylceramidePW_C007187Lacto18886Phosphoadenosine phosphosulfateHMDB00011343'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.482-67-7C000531021417980PAPS9799NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1OC10H15N5O13P2SInChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1GACDQMDRPRGCTN-KQYNXXCUSA-N507.264506.986229305FDB0224453'-phospho-5'-adenylyl sulfate;3'-phosphoadenosine 5'-phosphosulfate;3'-phosphoadenosine-5'-phosphosulfate;3'-phosphoadenylyl sulfate;3'-phosphoadenylyl-sulfate;5-phosphoadenosine 3-phosphosulfate;Paps;Phosphoadenosine phosphosulfate;3'-phospho-5'-adenylyl sulphate;3'-phosphoadenosine 5'-phosphosulphate;3'-phosphoadenosine-5'-phosphosulphate;3'-phosphoadenylyl sulphate;3'-phosphoadenylyl-sulphate;5-phosphoadenosine 3-phosphosulphate;Phosphoadenosine phosphosulphate;3'-phosphoadenosine 5'-phosphosulfuric acid;3'-phosphoadenosine 5'-phosphosulphuric acidPW_C000886Paps1249822054345851848933151989758431437251214843615143376277346111788873567998313212096012212210641912269912412352513512465745512528611812590029712626149012683729912736120512782550712844438878463-O-Sulfogalactosylceramide (d18:1/18:0)HMDB00123143-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS).244215-65-4C061255771775GALACTOSYLCERAMIDE-SULFATE4696849CCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(=O)(O)=O)C1O)[C@@](O)([H])\C=C\CCCCCCCCCCCCCC42H81NO11SInChI=1S/C42H81NO11S/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)34-52-42-40(48)41(54-55(49,50)51)39(47)37(33-44)53-42/h29,31,35-37,39-42,44-45,47-48H,3-28,30,32-34H2,1-2H3,(H,43,46)(H,49,50,51)/b31-29+/t35-,36+,37+,39-,40?,41?,42+/m0/s1GQQZXRPXBDJABR-XMDONHODSA-N808.158807.553033129C061253'-o-sulphogalactosylceramide;3-o-sulfo-beta-d-galactosylceramide;3-o-sulfo-beta-delta-galactosylceramide;3-o-sulfogalactosylceramide;Cerebroside 3-sulfate;Galactosylceramide-sulfate;Galactosylceramidesulfate;N-[(1s,2r,3e)-2-hydroxy-1-[[(3-o-sulfo-b-d-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-octadecanamide;N-[(1s,2r,3e)-2-hydroxy-1-[[(3-o-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-octadecanamide;Sulfatide;Sulfatide (d18:1/18:0);[r-[r*,s*-(e)]]-n-[2-hydroxy-1-[[(3-o-sulfo-b-d-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-octadecanamide;[r-[r*,s*-(e)]]-n-[2-hydroxy-1-[[(3-o-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-octadecanamide;Cerebroside 3-sulphate;Galactosylceramide-sulphate;GalactosylceramidesulphatePW_C0078463OSs43Adenosine 3',5'-diphosphateHMDB0000061Adenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy.1053-73-2C00054159296179853-5-ADP140102NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1C10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1WHTCPDAXWFLDIH-KQYNXXCUSA-N427.2011427.029414749FDB0218873'-phosphoryl-amp;3,5-adp;3,5-diphosphoadenosine;3-phosphoadenosine 5-phosphate;5-(dihydrogen phosphate) 3-adenylate;5-(dihydrogen phosphate)3'-adenylic acid;Adenosine 3',5'-bisphosphate;Adenosine 3,5-bis;Adenosine 3,5-bisphosphate;3'-phosphoadenylate;Pap;Phosphoadenosine phosphate;3'-phosphoadenylic acid;Adenosine 3',5'-bismonophosphoric acid;Adenosine 3',5'-bisphosphoric acid;Phosphoadenosine phosphoric acidPW_C000043A3'5'PP125182207434587184895315200975845143725321484371514337727734811178889356799851321209631221221084191227011241235281351246594551252881181259032971262634901268392991273642051278275071284463881118SulfateHMDB0001448The sulfate ion is a polyatomic anion with the empirical formula SO42- and a molecular mass of 96.06 daltons; it consists of one central sulfur atom surrounded by four equivalent oxygen atoms in a tetrahedral arrangement. The sulfate ion carries a negative two charge and is the conjugate base of the hydrogen sulfate ion, HSO4-, which is the conjugate base of H2SO4, sulfuric acid. In inorganic chemistry, a sulfate (IUPAC-recommended spelling; also sulphate in British English) is a salt of sulfuric acid. Sulfate aerosols can act as cloud condensation nuclei and this leads to greater numbers of smaller droplets of water. Lots of smaller droplets can diffuse light more efficiently than just a few larger droplets.14808-79-8C00059111716189NH42SO41085OS(O)(=O)=OH2O4SInChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)QAOWNCQODCNURD-UHFFFAOYSA-N98.07897.967379242FDB022629Sulfate (ion 2-);Sulfate anion;Sulfate anion(2-);Sulfate dianion;Sulfate ion;Sulfate ion (so42-);Sulfate(2-);Sulfuric acid ion(2-);Sulphate;[so4](2-);So4(2-);Sulphate ion;Sulfuric acid;Sulphuric acid;Sulfuric acid anion(2-);Sulphate anion(2-);Sulphuric acid anion(2-);Sulfuric acid dianion;Sulphate dianion;Sulphuric acid dianion;Sulfuric acid ion;Sulphuric acid ion;Sulfuric acid(2-);Sulphate(2-);Sulphuric acid(2-);Sulfate ion(2-);Sulphate ion(2-);Sulphuric acid ion(2-)PW_C001118SO412423220994883496268108626910772542157353188735518742470318424713157720522577388331788911137900111212095340712211012612235238312351911912466144312490539812589448112626430112653249512735520612782820712810439093D-GalactoseHMDB0000143D-Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-Galactose are important not only for the provision of these pathways but also for the prevention of D-Galactose and D-Galactose metabolite accumulation. The main source of D-Galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-Galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-Galactose-1-phosphate. In the presence of D-Galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-Galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-Galactose-1-phosphate. Classic galactosemia-a term that denotes the presence of D-Galactose in the blood is the rare inborn error of D-Galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-Galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene. (PMID: 15256214, 11020650, 10408771).59-23-4C0098443935728061GALACTOSE388480OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1OC6H12O6InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1WQZGKKKJIJFFOK-PHYPRBDBSA-N180.1559180.063388116FDB012703(+)-galactose;5abp;8abp;D-(+)-galactose;D-galactose;D-hexose;Gal;Gla;Glc;Galactose;Galactose (nf);Hexose;Alpha d-galactose;Alpha-d-galactopyranose;Alpha-d-galactose;Alpha-d-gal;Gal-alpha;A d-galactose;α d-galactose;A-d-gal;α-d-gal;Gal-a;Gal-αPW_C000093D-Gal11428221292680602731613133293937517255215125711517789611377943336782373527825035378251326784101111208401221212211261212714291223864361223924371223934161234251351237914431238424641249404711249624721249634521258312971262663011272842051278302072210Galabiosylceramide (d18:1/18:0)HMDB0004834Galabiosylceramide is a non-acidic diglycosphingolipids, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit. It is a vital component of cellular membranes of most eukaryotic organisms and some bacteria. Its abundance relative to other lipids is usually low other than in epithelial and neuronal cells. Galabiosylceramide has also been found in small amounts in kidney and pancreas, for example. Galabiosylceramide is one of the lipids that accumulates in excessive amounts in Fabry's disease. It is the precursor of the gala series of oligoglycosylceramides.An animal tissues, biosynthesis involves addition of a second monosaccharides unit from the appropriate sugar nucleotide to a monoglycosylceramide, catalysed by a glycosyl transferase, in the lumen of the Golgi apparatus. Glycolipids are important components of the body's immune defense system, either in haptenic reactivity or in antibody-producing potency, i.e. as cellular immunogens or antigens. Certain glycolipids are involved in the antigenicity of blood group determinants, while others bind to specific toxins or bacteria. Some also function as receptors for cellular recognition, and they can be specific for particular tissues or tumours.77538-38-6C061262005727516744851CCCCCCCCCCCCCCCCCC(=O)NC(CO[C@@H]1O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)C(O)\C=C/CCCCCCCCCCCCCC48H91NO13InChI=1S/C48H91NO13/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-59-47-45(58)43(56)46(39(34-51)61-47)62-48-44(57)42(55)41(54)38(33-50)60-48/h29,31,36-39,41-48,50-52,54-58H,3-28,30,32-35H2,1-2H3,(H,49,53)/b31-29-/t36?,37?,38-,39-,41+,42+,43-,44-,45-,46+,47-,48-/m1/s1VOZHMDQUIRUFQW-NVIQELJCSA-N890.235889.649042003FDB0234351-o-(4-o-alpha-d-galactopyranosyl-beta-d-galactopyranosyl)-ceramide;1-o-(4-o-alpha-delta-galactopyranosyl-beta-delta-galactopyranosyl)-ceramide;Digalactosylceramide;Gal-alpha1->4gal-beta1->1'cerPW_C002210Galabio104814N-Acetylneuraminyl-galactosylceramide (d18:1/18:0)N-Acetylneuraminyl-galactosylceramide is a sialomonoglycosylceramide having N-acetyl-α-neuraminosyl-(2→3)-β-D-galactosyl as the sialomonoglycosyl component (ChEBI).[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)COC53H98N2O16InChI=1S/C53H98N2O16/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-44(62)55-39(40(59)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)37-68-51-48(65)50(47(64)43(36-57)69-51)71-53(52(66)67)34-41(60)45(54-38(3)58)49(70-53)46(63)42(61)35-56/h30,32,39-43,45-51,56-57,59-61,63-65H,4-29,31,33-37H2,1-3H3,(H,54,58)(H,55,62)(H,66,67)/b32-30+/t39-,40+,41-,42+,43+,45+,46+,47-,48+,49+,50-,51+,53-/m0/s1ZZZGALYQBDIVPQ-TUMZNNEGSA-N1019.3651018.691635084GM4 (d18:1/18:0)PW_C104814NAG9795ZincHMDB0015532Zinc is an essential element, necessary for sustaining all life. It is a trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen cell types in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system, and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Zinc deficiency is associated with anemia, short stature, hypogonadism, impaired wound healing, and geophagia. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature and shows that just micromolar amounts of the free ion kill some organisms.7440-66-6239942736322430DB01593[Zn++]ZnInChI=1S/Zn/q+2PTFCDOFLOPIGGS-UHFFFAOYSA-N65.40963.92914657830zn;Cinc;Zincum;Zink;Zn;Zn(ii);Zn2+PW_C009795Zinc5781711219043213717215449361029408374469184543144999316689107669010166991087020160117581151222915112633654239731542399318770302537802313278328112788111111201191241208981221223084071228521181234691351248601191254862991264744811270233881273172051280432066709CerP(d18:1/18:0)HMDB0010701CerP(d18:1/18:0) is a ceramide 1-phosphate belonging to the sphingolipid class of molecules. Ceramides are amides of fatty acids with long-chain di- or trihydroxy bases, the commonest in animals being sphingosine and in plants phytosphingosine. The acyl group of ceramides is generally a long-chain saturated or monounsaturated fatty acid. The most frequent fatty acids found in animal ceramides are 18:0, 24:0 and 24:1(n-9). Ceramide 1-phosphates are produced by phosphorylation of ceramide by a specific ceramide kinase. Ceramide-1-phosphate was shown to be a specific and potent inducer of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of the cytoplasmic phospholipase A2.5283583731444446696CCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCCC36H72NO6PInChI=1S/C36H72NO6P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(39)37-34(33-43-44(40,41)42)35(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38H,3-28,30,32-33H2,1-2H3,(H,37,39)(H2,40,41,42)/b31-29+/t34-,35+/m0/s1ZQQLMECVOXKFJK-NXCSZAMKSA-N645.9337645.509725553N-(octadecanoyl)-sphing-4-enine-1-phosphate;[(e,2s,3r)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl] dihydrogen phosphate;C18 cerp;Cerp(d18:1/18:0);N-octadecanoylsphing-4-enine 1-phosphate;N-stearoylsphing-4-enine 1-phosphate;N-stearoylsphingosine 1-phosphate;N-octadecanoylsphingosine 1-phosphoric acid;N-octadecanoylsphing-4-enine 1-phosphoric acid;N-stearoylsphing-4-enine 1-phosphoric acid;N-stearoylsphingosine 1-phosphoric acidPW_C006709CerP18104815Galabiosylceramide sulfate (d18:1/18:0)Galabiosylceramide sulfate is a non-acidic diglycosphingolipid, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit.CCCCCCCCCCCCCCCCCC(=O)NC(CO[C@@H]1O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](OS(O)(=O)=O)[C@H]2O)[C@H](O)[C@H]1O)C(O)\C=C/CCCCCCCCCCCCCC48H91NO16SInChI=1S/C48H91NO16S/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-61-47-43(56)42(55)45(39(34-51)63-47)64-48-44(57)46(65-66(58,59)60)41(54)38(33-50)62-48/h29,31,36-39,41-48,50-52,54-57H,3-28,30,32-35H2,1-2H3,(H,49,53)(H,58,59,60)/b31-29-/t36?,37?,38-,39-,41+,42-,43-,44-,45+,46+,47-,48-/m1/s1JMXDOGIVEGVEOO-CACNWILLSA-N970.31969.605857028Galabiosylceramide-sulfate (d18:1/18:0);Digalactosylceramide sulfate (d18:1/18:0);Digalactosylceramide-sulfate (d18:1/18:0)PW_C104815GalacSO77D-GlucoseHMDB0000122Glucose is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis.2280-44-6C0003157934167GLC5589[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])OC6H12O6InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1WQZGKKKJIJFFOK-GASJEMHNSA-N180.1559180.063388116FDB012530Roferose st;(+)-glucose;Anhydrous dextrose;Cpc hydrate;Cerelose;Cerelose 2001;Clearsweet 95;Clintose l;Corn sugar;D(+)-glucose;Dextropur;Dextrose;Dextrosol;Glucodin;Glucolin;Glucose;Goldsugar;Grape sugar;Meritose;Staleydex 111;Staleydex 95m;Tabfine 097(hs);Vadex;D-glc;D-glcp;D-glucosePW_C000077D-Glc1452501460261461511506215404321939243942679602721152723613027663114293593356926589614859221495923152595415363671076368108686919269041937085200724421511765114117661324244031842441315770853267711732777923336779893467823635278248353782623567888111379056112121166424121167416121169423121251429121361124121373419122098126122385436122388437122399407122676409123738459123739452123741458123821464123920118123932455124649443124939471124959472124969119125251137125937488125967492126034299126046490126254301126540481126809483127397505127423509127486388127498507127817207128113206128408208831Serine palmitoyltransferase 2O15270Serine palmitoyltransferase (SPT). The heterodimer formed with LCB1/SPTLC1 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC2-SPTSSB complex displays a preference for C18-CoA substrate.
HMDBP00888SPTLC214q24.3BC00512312.3.1.5020982829Serine palmitoyltransferase 1O15269Serine palmitoyltransferase (SPT). The heterodimer formed with SPTLC2 or SPTLC3 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC3-SPTSSA isozyme uses both C14-CoA and C16-CoA as substrates, with a slight preference for C14-CoA. The SPTLC1-SPTLC2-SPTSSB complex shows a strong preference for C18-CoA substrate, while the SPTLC1-SPTLC3-SPTSSB isozyme displays an ability to use a broader range of acyl-CoAs, without apparent preference.
HMDBP00886SPTLC19q22.2AF28670612.3.1.502099222173-ketodihydrosphingosine reductaseQ06136Catalyzes the reduction of 3-ketodihydrosphingosine (KDS) to dihydrosphingosine (DHS).
HMDBP03056KDSR18q21.3X6365711.1.1.102210121017Sphingosine kinase 2Q9NRA0Catalyzes the phosphorylation of sphingosine to form sphingosine 1-phosphate (SPP), a lipid mediator with both intra- and extracellular functions. Also acts on D-erythro-dihydrosphingosine, D-erythro-sphingosine and L-threo-dihydrosphingosine. Binds phosphoinositides.
HMDBP01083SPHK219q13.2AL13670112.7.1.9121032212510214749139858145206Sphingosine-1-phosphate phosphatase 2Q8IWX5Has specific phosphohydrolase activity towards sphingoid base 1-phosphates. Has high phosphohydrolase activity against dihydrosphingosine-1-phosphate and sphingosine-1-phosphate (S1P) in vitro. May play a role in attenuating intracellular sphingosine 1-phosphate (S1P) signaling. May play a role in pro-inflammatory signaling.
HMDBP11558SGPP2BC13434213.1.3.-210618212610215249231Lipid phosphate phosphohydrolase 1O14494Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
HMDBP00237PPAP2A5q11AF01440213.1.3.4153914337918461910138435211989Sphingosine-1-phosphate lyase 1O95470Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
HMDBP01052SGPL110q21AJ01130414.1.2.272121102151492638Sphingolipid delta(4)-desaturase/C4-hydroxylase DES2Q6QHC5Bifunctional enzyme which acts as both a sphingolipid delta(4)-desaturase and a sphingolipid C4-hydroxylaseHMDBP07414DEGS214q32.2AY54170011.-.-.-; 1.14.-.-2131104723Alkaline ceramidase 1Q8TDN7Hydrolyzes the sphingolipid ceramide into sphingosine and free fatty acid at an optimal pH of 8.0. Has a highly restricted substrate specificity for the natural stereoisomer of ceramide with D-erythro-sphingosine but not D-ribo-phytosphingosine or D-erythro-dihydrosphingosine as a backbone. May have a role in regulating the levels of bioactive lipids ceramide and sphingosine 1-phosphate, as well as complex sphingolipids (By similarity).
HMDBP10638ACER119p13.3BC11212213.5.1.232128102153491308Ceramide kinaseQ8TCT0Catalyzes specifically the phosphorylation of ceramide to form ceramide 1-phosphate. Acts efficiently on natural and analog ceramides (C6, C8, C16 ceramides, and C8-dihydroceramide), to a lesser extent on C2-ceramide and C6-dihydroceramide, but not on other lipids, such as various sphingosines. Binds phosphoinositidesHMDBP01405CERK22q13.31AB07906612.7.1.138215814720Phosphatidylcholine:ceramide cholinephosphotransferase 1Q86VZ5Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Suppresses BAX-mediated apoptosis and also prevents cell death in response to stimuli such as hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. May protect against cell death by reversing the stress-inducible increase in levels of proapoptotic ceramide. Required for cell growthHMDBP00775SGMS110q11.2AB15442112.7.8.272166431023Ectonucleotide pyrophosphatase/phosphodiesterase family member 7Q6UWV6Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
HMDBP01089ENPP717q25.3AK12625013.1.4.1221684310352-hydroxyacylsphingosine 1-beta-galactosyltransferaseQ16880Catalyzes the transfer of galactose to ceramide, a key enzymatic step in the biosynthesis of galactocerebrosides, which are abundant sphingolipids of the myelin membrane of the central nervous system and peripheral nervous system.
HMDBP01101UGT84q26BC07506912.4.1.45217049309GalactocerebrosidaseP54803Hydrolyzes the galactose ester bonds of galactosylceramide, galactosylsphingosine, lactosylceramide, and monogalactosyldiglyceride. Enzyme with very low activity responsible for the lysosomal catabolism of galactosylceramide, a major lipid in myelin, kidney and epithelial cells of small intestine and colon.
HMDBP00315GALC14q31L3855513.2.1.46217149218991612GlucosylceramidaseP04062HMDBP01795GBA1q21AL71399913.2.1.4521949790Ceramide glucosyltransferaseQ16739Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
HMDBP00845UGCG9q31AK31484712.4.1.802198494788Beta-galactosidaseP16278
Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans.
HMDBP10706GLB1AK22276313.2.1.232200231049310629144273262504Beta-1,4-galactosyltransferase 6Q9UBX8Required for the biosynthesis of glycosphingolipids.
HMDBP07258B4GALT618q11BC07483512.4.1.-; 2.4.1.274220443312Galactosylceramide sulfotransferaseQ99999Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of galactosylceramide sulfate (sulfatide), a major lipid component of the myelin sheath and of monogalactosylalkylacylglycerol sulfate (seminolipid), present in spermatocytes (By similarity). Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro).
HMDBP00318GAL3ST122q12.2BC01907712.8.2.11220843314Arylsulfatase AP15289Hydrolyzes cerebroside sulfate.
HMDBP00320ARSA22q13.33AY27182013.1.6.834281403222109686Alpha-galactosidase AP06280HMDBP00723GLAM2031713.2.1.2222139313Sialidase-3Q9UQ49Plays a role in modulating the ganglioside content of the lipid bilayer at the level of membrane-bound sialyl glycoconjugatesHMDBP00319NEU311q13.5AB00818513.2.1.182191494467182637Alkaline ceramidase 3Q9NUN7Hydrolyzes only phytoceramide into phytosphingosine and free fatty acid. Does not have reverse activity.
HMDBP07413ACER3AF32735313.5.1.-21391721554944701844712549Serine palmitoyltransferase 11PW_P00054958983115908291266114815503-ketodihydrosphingosine reductase1PW_P00055059122171551Sphingosine kinase 21PW_P000551592101712674231552Sphingosine-1-phosphate phosphatase 21PW_P00055259352061418Lipid phosphate phosphohydrolase 11PW_P000418440231554Sphingosine-1-phosphate lyase 11PW_P000554595989126811481556Sphingolipid delta(4)-desaturase/C4-hydroxylase DES21PW_P00055659726381213210555Alkaline ceramidase 11PW_P00055559647231559Ceramide kinase1PW_P0005596001308127135312724231560Phosphatidylcholine:ceramide cholinephosphotransferase 11PW_P0005606017201561Ectonucleotide pyrophosphatase/phosphodiesterase family member 71PW_P000561602102315622-hydroxyacylsphingosine 1-beta-galactosyltransferase1PW_P00056260310351563Galactocerebrosidase1PW_P0005636043091570Glucosylceramidase1PW_P00057061116121571Ceramide glucosyltransferase1PW_P0005716127901572Beta-galactosidase1PW_P00057261347881574Beta-1,4-galactosyltransferase 61PW_P000574615250412754231575Galactosylceramide sulfotransferase1PW_P000575616312138Arylsulfatase A1PW_P00003839314576Alpha-galactosidase A1PW_P0005766176861569Sialidase-31PW_P0005696103131557Alkaline ceramidase 31PW_P000557598263712699795127035311168falsePW_R001168Right447810311Compoundfalse44791201Compoundfalse448011391Compoundfalse448113161Compoundtrue8685492.3.1.501169falsePW_R001169Right44821841Compoundfalse44831461Compoundtrue448411391Compoundfalse44851431Compoundtrue8695501.1.1.102519falsePW_R000519Right21674141Compoundtrue21681841Compoundfalse216910341Compoundtrue217010701Compoundfalse8725512.7.1.911170falsePW_R001170Right448610701Compoundfalse448710341Compoundtrue44881841Compoundfalse44894141Compoundtrue8735523.1.3.-1171falsePW_R001171Right449010701Compoundfalse449114201Compoundtrue44921841Compoundfalse449311041Compoundtrue8744183.1.3.4511falsePW_R000511Right213210701Compoundfalse21331491Compoundfalse213411931Compoundtrue8865544.1.2.271186falsePW_R001186Unknown452729051Compoundfalse452823131Compoundfalse8905561193falsePW_R001193Right45451881Compoundfalse45461491Compoundfalse454711931Compoundtrue8975544.1.2.271194falsePW_R001194Right45481721Compoundfalse45494141Compoundtrue45501881Compoundfalse455110341Compoundtrue8985512.7.1.911195falsePW_R001195Right45521881Compoundfalse455310341Compoundtrue45541721Compoundfalse45554141Compoundtrue8995523.1.3.-1196falsePW_R001196Right45561721Compoundfalse455711041Compoundtrue45581881Compoundfalse455914201Compoundtrue9004183.1.3.41197falsePW_R001197Right456023131Compoundfalse456114201Compoundtrue45621721Compoundfalse9015553.5.1.231203falsePW_R001203Right457923131Compoundfalse458039901Compoundtrue458110401Compoundfalse458229281Compoundtrue9075602.7.8.271204falsePW_R001204Right458310401Compoundfalse458414201Compoundtrue458523131Compoundfalse458612021Compoundtrue9085613.1.4.121205falsePW_R001205Right458723131Compoundfalse458867171Compoundfalse9095622.4.1.451206falsePW_R001206Right458967171Compoundfalse459023131Compoundfalse9105633.2.1.461218falsePW_R001218Right463023131Compoundfalse46311931Compoundtrue463223341Compoundfalse46332011Compoundtrue9225712.4.1.801219falsePW_R001219Right463471871Compoundfalse463523341Compoundfalse9235723.2.1.231221falsePW_R001221Left464071871Compoundfalse46412011Compoundtrue464223341Compoundfalse46431931Compoundtrue9255741222falsePW_R001222Right464467171Compoundfalse46458861Compoundtrue464678461Compoundfalse4647431Compoundtrue9265752.8.2.111223falsePW_R001223Right464878461Compoundfalse464914201Compoundtrue465067171Compoundfalse465111181Compoundtrue927383.1.6.81225falsePW_R001225Left465767171Compoundfalse4658931Compoundtrue465922101Compoundfalse9305763.2.1.221227falsePW_R001227Right466467171Compoundfalse46651048141Compoundfalse9325693.2.1.181198falsePW_R001198Right456329051Compoundfalse45641841Compoundfalse9025573.5.1.-1200falsePW_R001200Right456967091Compoundfalse457014201Compoundtrue457123131Compoundfalse457211041Compoundtrue9044183.1.3.41201falsePW_R001201Right457323131Compoundfalse457467091Compoundfalse9055523.1.3.-1199falsePW_R001199Right456523131Compoundfalse45664141Compoundtrue456767091Compoundfalse456810341Compoundtrue9035592.7.1.138180411falsePW_R180411Right68123722101Compoundfalse6812388861Compoundtrue681240431Compoundtrue6812421048151Compoundfalse1702695752.8.2.111216falsePW_R001216Right462223341Compoundfalse462314201Compoundtrue462423131Compoundfalse4625771Compoundtrue9205703.2.1.4538731031281false22046010regular2001903874120281false21579510regular20019038751139281false85026510regular20019038761316281true87058510regular2001903877114829false67049510regular100353878184281false136526010regular2001903879146262false130043510regular50303880143261false106543510regular50303881414242false157044510regular503038821034243false180044510regular503038831070281false182525010regular200190388442329false164547510regular10025388510341843false182565510regular503038864141842false153065010regular503038871420143true182514010regular100100388811041446false152520010regular444339101491081false225026010regular200190391111931081true219025510regular20019039121148109false210550510regular10035392423131081false366546510regular200190392829051081false350583510regular20019039411884981false263526010regular20019039421193493true232022010regular10010039431148499false249049510regular1003539441724981false310026010regular20019039454144942false305545010regular5030394610344943false281545510regular50303947423499false291548010regular10025394810344943false281065510regular503039494144942false306566010regular5030395011041446false308520010regular444339511420143true263515510regular10010039521420493true361036510regular10010039554141442false396548010regular5030395710341443false418061510regular50303958353149false411051210regular100253959423149false411049210regular10025396311041446false390560510regular4443396739904381true380532010regular200190396810404381false36558010regular200190396929284381true335021510regular20019039761420433true325015510regular10010039771202433true349046510regular100100398067174981false3045158510regular20020040142334981false2330157010regular2001904020193493true360032510regular1001204021201493true2550134010regular10011040227187281false1715157510regular2001904026201433true191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555 C450 555 615 555 645 555 5false185682M315 795 C314 683 572 555 645 555 5false185683M950 455 C951 531 888 552 795 555 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5684M870 635 C840 635 825 555 795 555 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5685M175 250 L175 300 L225 250 z10true185686M1465 450 C1470 551 1315 555 1285 555 5false185687M1325 465 C1329 496 1315 555 1285 555 5false185688M950 455 C952 520 1020 556 1135 555 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5689M1090 465 C1091 516 1106 555 1135 555 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5690M1595 475 C1595 508 1595 520 1625 520 5false185691M1465 450 C1467 493 1587 520 1625 520 5false185692M1825 475 C1825 514 1805 520 1775 520 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5693M1925 440 C1924 521 1805 520 1775 520 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5694M1700 345 L1700 395 L1750 345 z10true185695M1925 440 C1927 530 1879 597 1775 600 5false185696M1850 655 C1850 603 1805 600 1775 600 5false185697M1465 450 C1471 565 1595 600 1625 600 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5698M1555 650 C1556 622 1595 600 1625 600 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5699M1925 250 C1911 177 1790 130 1760 130 5false185700M1825 190 C1795 190 1790 130 1760 130 5true185701M1465 260 C1459 187 1580 130 1610 130 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5702M1547 200 C1546 181 1580 130 1610 130 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5737M1925 440 C1926 524 2050 565 2080 565 5false185738M2350 450 C2351 542 2284 565 2230 565 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5739M2290 445 C2301 522 2260 565 2230 565 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5740M2150 455 L2150 505 L2200 455 z10true185763M3605 835 C3605 811 3605 835 3605 805 5false185764M3765 655 C3656 653 3605 705 3605 735 5false185785M2735 450 C2735 523 2646 554 2615 555 5false185786M2350 450 C2354 510 2390 554 2465 555 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5787M2420 270 C2450 270 2435 555 2465 555 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5788M2645 315 L2645 365 L2695 315 z10true185789M3200 450 C3190 525 3070 530 3040 530 5false185790M3080 480 C3080 503 3064 529 3040 530 5false185791M2735 450 C2737 523 2860 530 2890 530 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5792M2840 485 C2841 514 2863 531 2890 530 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5793M2960 370 L2960 420 L3010 370 z10true185794M2735 450 C2737 566 2857 610 2887 610 5false185795M2835 655 C2835 626 2857 610 2887 610 5false185796M3200 450 C3205 570 3067 610 3037 610 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5797M3090 660 C3090 624 3067 610 3037 610 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5798M3200 260 C3202 179 3072 125 3042 125 5false185799M3107 200 C3107 181 3072 125 3042 125 5false185800M2735 260 C2748 179 2862 125 2892 125 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5801M2735 205 C2765 205 2862 125 2892 125 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5802M3665 560 C3635 560 3525 560 3495 560 5false185803M3610 415 C3580 415 3525 560 3495 560 5true185804M3200 450 C3211 534 3315 560 3345 560 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5813M4045 507 L4045 557 L4095 507 z10true185814M4045 487 L4045 537 L4095 487 z10true185831M3665 560 C3589 560 3562 413 3560 395 5false185832M3905 320 C3905 290 3560 425 3560 395 5true185833M3655 175 C3604 174 3558 264 3560 325 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5834M3550 310 C3591 322 3560 295 3560 325 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5841M3855 175 C3922 177 3955 300 3955 330 5false185842M3300 255 C3300 285 3955 300 3955 330 5true185843M3865 560 C3936 559 3954 419 3955 400 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5844M3540 465 C3540 435 3955 430 3955 400 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5847M3665 617 C3483 620 3213 1047 3215 1227 5false185848M3216 1579 C3216 1549 3215 1327 3215 1297 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5899M3055 1585 C3055 1555 3055 1545 3055 1515 5false185900M3661 597 C3384 607 3046 1101 3055 1445 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5911M3665 560 C3260 587 2353 1085 2350 1235 5false185912M3600 385 C3570 385 2455 1270 2425 1270 5true185913M2344 1565 C2345 1490 2349 1361 2350 1305 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false5914M2650 1395 C2680 1395 2245 1270 2275 1270 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 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