80PathwayVitamin K MetabolismVitamin K describes a group of lipophilic, hydrophobic vitamins that exist naturally in two forms (and synthetically in three others): vitamin K1, which is found in plants, and vitamin K2, which is synthesized by bacteria. Vitamin K is an important dietary component because it is necessary as a cofacter in the activation of vitamin K dependent proteins. Metabolism of vitamin K occurs mainly in the liver. In the first step, vitamin K is reduced to its quinone form by a quinone reductase such as NAD(P)H dehydrogenase. Reduced vitamin K is the form required to convert vitamin K dependent protein precursors to their active states. It acts as a cofactor to the integral membrane enzyme vitamin K-dependent gamma-carboxylase (along with water and carbon dioxide as co-substrates), which carboxylates glutamyl residues to gamma-carboxy-glutamic acid residues on certain proteins, activating them. Each converted glutamyl residue produces a molecule of vitamin K epoxide, and certain proteins may have more than one residue requiring carboxylation. To complete the cycle, the vitamin K epoxide is returned to vitamin K via the vitamin K epoxide reductase enzyme, also an integral membrane protein. The vitamin K dependent proteins include a number of important coagulation factors, such as prothrombin. Thus, warfarin and other coumarin drugs act as anticoagulants by blocking vitamin K epoxide reductase.MetabolicPW000047CenterPathwayVisualizationContext4727501750#000099PathwayVisualization5780Vitamin K MetabolismVitamin K describes a group of lipophilic, hydrophobic vitamins that exist naturally in two forms (and synthetically in three others): vitamin K1, which is found in plants, and vitamin K2, which is synthesized by bacteria. Vitamin K is an important dietary component because it is necessary as a cofacter in the activation of vitamin K dependent proteins. Metabolism of vitamin K occurs mainly in the liver. In the first step, vitamin K is reduced to its quinone form by a quinone reductase such as NAD(P)H dehydrogenase. Reduced vitamin K is the form required to convert vitamin K dependent protein precursors to their active states. It acts as a cofactor to the integral membrane enzyme vitamin K-dependent gamma-carboxylase (along with water and carbon dioxide as co-substrates), which carboxylates glutamyl residues to gamma-carboxy-glutamic acid residues on certain proteins, activating them. Each converted glutamyl residue produces a molecule of vitamin K epoxide, and certain proteins may have more than one residue requiring carboxylation. To complete the cycle, the vitamin K epoxide is returned to vitamin K via the vitamin K epoxide reductase enzyme, also an integral membrane protein. The vitamin K dependent proteins include a number of important coagulation factors, such as prothrombin. Thus, warfarin and other coumarin drugs act as anticoagulants by blocking vitamin K epoxide reductase.Metabolic115142011694380Pathway1515Litwack G. ed. Vitamins and Hormones: Vitamin K. (2008) 78. New York: Academic Press, Elsevier80Pathway15161610205480Pathway1CellCL:00000005HepatocyteCL:00001823NeuronCL:000054012AstrocyteCL:00001274CardiomyocyteCL:00007467Epithelial CellCL:00000662Platelet CL:00002331Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum6LysosomeGO:00057644PeroxisomeGO:00057775CytoplasmGO:00057372MitochondrionGO:00057393Mitochondrial MatrixGO:000575912Mitochondrial Inner MembraneGO:000574316Lysosomal LumenGO:004320213Endoplasmic ReticulumGO:00057831CytosolGO:000582910Cell MembraneGO:000588624Mitochondrial Intermembrane SpaceGO:00057587Endoplasmic Reticulum MembraneGO:000578914Mitochondrial Outer MembraneGO:000574120Endoplasmic Reticulum LumenGO:000578831Periplasmic SpaceGO:000562035ChloroplastGO:000950734Plant-Type VacuoleGO:000032539Mitochondrial membraneGO:003196611Extracellular SpaceGO:000561536MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016832Inner MembraneGO:007025825Golgi ApparatusGO:000579418Melanosome MembraneGO:003316221SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425971LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:0001102741124BrainBTO:000014289164Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273106KidneyBTO:00006717182Endothelium BTO:00003939611PW_BS0000095411PW_BS0000058511PW_BS0000083211PW_BS0000034311PW_BS000004171211PW_BS0000172811611PW_BS000028181311PW_BS0000182111PW_BS00000214101PW_BS000014422411PW_BS00004229111PW_BS00002949711PW_BS0000495811411PW_BS000058221411PW_BS000022261115PW_BS0000263612011PW_BS000036311511PW_BS00003113121PW_BS000013101711PW_BS0000106131PW_BS000006103331PW_BS0001031021231PW_BS0001021115121PW_BS000111126651PW_BS00012612711651PW_BS0001271181171PW_BS0001181553241PW_BS00015515612241PW_BS0001561613181PW_BS00016116212181PW_BS00016211PW_BS0000011783211PW_BS00017817912211PW_BS000179107313PW_BS0001071632181PW_BS000163205561PW_BS0000242137181PW_BS000024222341PW_BS0000242231241PW_BS000024224241PW_BS0000242164181PW_BS0000242156181PW_BS0000242111018PW_BS0000242253541PW_BS0000242491341PW_BS000024151141PW_BS0001512273441PW_BS000024226441PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000243183123PW_BS00002429341PW_BS0000241333121PW_BS00013313412121PW_BS0001341136121PW_BS0001131122121PW_BS0001121151012PW_BS0001153344121PW_BS0000281321121PW_BS000132337116121PW_BS00002832914121PW_BS00002834524121PW_BS0000283317121PW_BS0000283361121PW_BS0000283583912PW_BS0000283683601PW_BS00002836912601PW_BS0000281192171PW_BS000119406351PW_BS0001153841251PW_BS000100408451PW_BS000115407251PW_BS000115405105PW_BS000115122551PW_BS000122124151PW_BS000124429151PW_BS0001154182451PW_BS0001153821451PW_BS000100383751PW_BS0001001203171PW_BS00012012112171PW_BS0001213744171PW_BS0000534436171PW_BS0001153761017PW_BS0000531355171PW_BS000135448116171PW_BS0001154641171PW_BS00011545424171PW_BS00011539914171PW_BS0001133987171PW_BS0001134793101PW_BS00011548012101PW_BS0001154824101PW_BS0001154812101PW_BS0001152975101PW_BS00002448924101PW_BS0001152991101PW_BS00002448414101PW_BS000115501361PW_BS0001153911261PW_BS000112502461PW_BS000115207661PW_BS000024206261PW_BS000024209106PW_BS0000245062461PW_BS000115388161PW_BS0001123891461PW_BS000112185321PW_BS0000241861221PW_BS000024541315PW_BS000054951721PW_BS0000951231751PW_BS0001231251351PW_BS000125100521PW_BS00010010813PW_BS00010814117191PW_BS0001411471241PW_BS000147117131PW_BS0001171601181PW_BS000160188118PW_BS0000241985181PW_BS00002429817101PW_BS00002430013101PW_BS0000243221231PW_BS000024315123PW_BS00002433217121PW_BS00002813013121PW_BS00013034713125PW_BS000028943PW_BS0000944251355PW_BS00011544717171PW_BS00011513613171PW_BS00013646013175PW_BS0001154957101PW_BS000115390761PW_BS0001123951361PW_BS00011315111PW_BS0000157028511PW_BS000070105113PW_BS0001051572241PW_BS00015715924PW_BS00015916611PW_BS00016615284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS0001701951318PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242941141PW_BS0000243081011PW_BS0000243125231PW_BS0000243201123PW_BS0000241141112PW_BS00011432711125PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109409115PW_BS0001154241155PW_BS0001151371117PW_BS00013745911175PW_BS0001154831110PW_BS000115208116PW_BS00002488231202PW_BS00055288312021PW_BS000552167311PW_BS000167168321PW_BS000168788241113PW_BS00052459724112PW_BS000336432511PW_BS00004335625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS000115204111PW_BS000020331811PW_BS0000332441011PW_BS00002460251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS00011012915121PW_BS000129140103PW_BS00014014315191PW_BS0001431465191PW_BS0001461802211PW_BS00018021425181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS000024253541PW_BS0000243331212PW_BS00002834141121PW_BS00002834318121PW_BS0000283522512PW_BS00002835325127PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154151851PW_BS0001154141551PW_BS00011543441051PW_BS000115436255PW_BS0001154461217PW_BS00011545118171PW_BS00011545015171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154781010PW_BS00011548718101PW_BS0001155041861PW_BS00011551541061PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS00054916212PW_BS000016964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N785.5497785.157134455FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD99911451868192321642531762828825188402118814148942161229162249213358253622372326460236468831474113475810488165268103528510253351115496126551112756131186030155605415660821616116162639016475178649917966661077039163717520573212137465222748722390762241181821611887215118992111229622512328249124431511251922712595226127102911272029213029301130413024362331877080293771261337715213477501113775071127751811577541334776151327772633778054329783753457893033179222336792723588001236880034369807141191199584061199993841200514081201074071204324051204531221204901241212784291212984181214173821214893831227481201227761211228023741228234431230663761230871351231664481238494641238684541239763991240473981253484791253784801254294821254744811256972971259794891261072991262774841268915011269203911269685021269872071270112061273102091274325061276023881278403891407901851407991861746Vitamin K1 2,3-epoxideHMDB0002972Vitamin K1 2,3-epoxide is a vitamin K derivative. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Within the cell, vitamin K undergoes electron reduction to a reduced form of vitamin K (called vitamin K hydroquinone) by the enzyme vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes vitamin K hydroquinone to allow carboxylation of glutamate into gamma-carboxyglutamate (Gla). This enzyme is called the gamma-glutamyl carboxylase or the vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize vitamin K hydroquinone into vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted into vitamin K by the vitamin K epoxide reductase. These two enzymes comprise the so-called vitamin K cycle. One of the reasons why vitamin K is rarely deficient in a human diet is because vitamin K is continually recycled in our cells. Vitamin K 2,3-epoxide is the substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Significantly increased level of serum vitamin K epoxide has been found in patients with familial multiple coagulation factor deficiency (PMID: 12384421). Accumulation of vitamin K1-2,3-epoxide in plasma is also a sensitive marker of coumarin-like activity of drugs (PMID: 2401753).
25486-55-9C05849915772837123-EPOXY-23-DIHYDRO-2-METHYL-14-NAPHTHOQ82688CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\C[C@@]12O[C@]1(C)C(=O)C1=C(C=CC=C1)C2=OC31H46O3InChI=1S/C31H46O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-,30-,31+/m1/s1KUTXFBIHPWIDJQ-BTPXSFBUSA-N466.706466.344695341FDB023087(2,3-epoxyphytyl)menaquinone;1,4-naphthoquinone, 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-2,3-epoxyphylloquinone;2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone;2,3-epoxyphylloquinone;Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-phylloquinone oxide;Phylloquinone 2,3-epoxide;Phylloquinone-2,3-epoxide;Vitamin k 2,3-epoxide;Vitamin k epoxide;Vitamin k1 oxide;1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)-naphth[2,3-b]oxirene-2,7-dione;Phylloquinone epoxide;Phylloquinone oxide;Phylloquinone, epoxide;Vitamin k1 2,3-epoxide;Vitamin k1, epoxidePW_C001746VitKo49526147231166129456018792243361212814291238524641924Vitamin K1HMDB0003555Vitamin K1 or Phylloquinone is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K 1 (vitamin K 1) derived from plants, vitamin K 2 (menaquinone) from bacteria, and synthetic naphthoquinone provitamins, vitamin K 3 (menadione). Vitamin K1 has only one double bond on the proximal isoprene unit. Vitamin K1 possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants.84-80-0C0205952804835839723-HYDROXY-2-METHYL-3-PHYTYL-23-DIHYDRONA4444124DB01022CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=OC31H46O2InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1MBWXNTAXLNYFJB-NKFFZRIASA-N450.6957450.349780716FDB0123572',3'-trans-vitamin k1;2-methyl-3-[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione;2-methyl-3-phythyl-1,4-naphthochinon;2-methyl-3-phytyl-1,4-naphthochinon;2-methyl-3-phytyl-1,4-naphthoquinone;2-methyl-3-phytyl-1,4-napthoquinone;3-phytylmenadione;Antihemorrhagic vitamin;Aqua mephyton;Aqua-mephytin;Aquamephyton;Combinal k1;Fitomenadiona;Fitomenadione;K-ject;Kativ n;Kephton;Kinadion;Konakion;Mephyton;Mono-kay;Monodion;Phyllochinon;Phyllochinonum;Phylloquinone;Phythyl-menadion;Phytomenadione;Phytomenadionum;Phytonadione;Phytonadionum;Phytylmenadione;Synthex p;Vitamin k1;A-phylloquinone;Alpha-phylloquinone;Trans-phylloquinonePW_C001924VitK1160829792203361212744291238454641144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N665.441665.124771695FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH1434153349086481011152127551469542230492781172836293109948061848121848212849046495931516995524010353321115358112546612354791255593135569810057371085829141591514759451516027155607916163871647217867711176893160701118870991637172205719520674622228244226836022590862241180919811821216123202491300329813015300132552234240332242618315771071327712313377208134773713317765133677668334777003327770713077917113779863478000936880691119938221241105493881128549411583811811995540612017240712037812212098640812116242512124412612169342912181838312261638412274512012312744712313813612355137412373446012381444312424246412437139812518912112534547912553148112576229712580829912592648212651649512676748012688850112738550212809039012836239112842939514075918540034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-N1.00791.007825032H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951406928821406938831406991671407071681407151414074278814074359714076018557915PhylloquinolHMDB0060502Phylloquinol, also known as phytonadiol or dihydrovitamin K1, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, phylloquinol is considered to be a quinone lipid molecule. Phylloquinol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, phylloquinol is primarily located in the membrane (predicted from logP) and cytoplasm. Outside of the human body, phylloquinol can be found in a number of food items such as amaranth, strawberry, summer grape, and prunus (cherry, plum). This makes phylloquinol a potential biomarker for the consumption of these food products. Phylloquinol is the final product of phylloquinol biosynthesis.572-96-3C03313528058528433CPD-128314444201CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1CC31H48O2InChI=1S/C31H48O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1BUFJIHPUGZHTHL-NKFFZRIASA-N452.7116452.36543078[R-[R*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediol;2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenediol;(E)-2-Methyl-3-phytyl-1,4-naphthalenediol;2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthalenediol;2-Methyl-3-phytyl-1,4-naphthohydroquinone;Dihydrovitamin K1;Dihydro-phylloquinone;Phytonadiol;Reduced phylloquinone;Vitamin K1 hydroquinone;α-Phyllohydroquinone;alpha-PhyllohydroquinonePW_C057915Phyl12382225721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=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](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H27N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N663.4251663.109121631FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD1404150335386511011142113443127351466542229492779172835293107948071848131848192849026496031516795523810353341115360112546912354821255590135561011856961005738108582714159121475942151602415560721576076161638516469178677211768901607012188709716371742057197206740519874592228241226835922590852241181921612322249130062981301830013256223424043224261931577104132771201337720913477370331776503367766733477702332777091307791511377983347784063568000636880690119938251241105523881127501661128539411992912211995240612017140712083441912098440812115942512124212612125942912181738312261438412274212012313044712314113612341945512354937412373146012381244312382946412437039812518712112531929712534247912553048112580629912582549012592448212651549512676548012688550112727850712738350212808939012836039112842839514075718585091,4-DithiothreitolHMDB0013593Dithiothreitol (DTT) is the common name for a small-molecule redox reagent known as Cleland's reagent. DTT's formula is C4H10O2S2 and the molecular structure of its reduced form is shown at the right; its oxidized form is a disulfide-bonded 6-membered ring (shown below). Its name derives from the four-carbon sugar, threose. DTT has an epimeric ('sister') compound, dithioerythritol. A common use of DTT is as a reducing or "deprotecting" agent for thiolated DNA. The terminal sulfur atoms of thiolated DNA have a tendency to form dimers in solution, especially in the presence of oxygen. Dimerization greatly lowers the efficiency of subsequent coupling reactions such as DNA immobilization on gold in biosensors. Typically DTT is mixed with a DNA solution and allowed to react, and then is removed by filtration (for the solid catalyst) or by chromatography (for the liquid form). The DTT removal procedure is often called "desalting.". DTT is frequently used to reduce the disulfide bonds of proteins and, more generally, to prevent intramolecular and intermolecular disulfide bonds from forming between cysteine residues of proteins. However, even DTT cannot reduce buried (solvent-inaccessible) disulfide bonds, so reduction of disulfide bonds is sometimes carried out under denaturing conditions (e.g., at high temperatures, or in the presence of a strong denaturant such as 6 M guanidinium hydrochloride, 8 M urea, or 1% sodium dodecylsulfate). Conversely, the solvent exposure of different disulfide bonds can be assayed by their rate of reduction in the presence of DTT. DTT can also be used as an oxidizing agent. Its principal advantage is that effectively no mixed-disulfide species are populated, in contrast to other agents such as glutathione. In very rare cases, a DTT adduct may be formed, i.e., the two sulfur atoms of DTT may form disulfide bonds to different sulfur atoms; in such cases, DTT cannot cyclize since it has no remaining free thiols. Due to air oxidation, DTT is a relatively unstable compound whose useful life can be extended by refrigeration and handling in an inert atmosphere. Since protonated sulfurs have lowered nucleophilicities, DTT becomes less potent as the pH lowers. Tris(2-carboxyethyl)phosphine HCl (TCEP hydrochloride) is an alternative which is more stable and works even at low pH.3483-12-3C0026543919642106388336O[C@@H](CS)[C@@H](O)CSC4H10O2S2InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1VHJLVAABSRFDPM-IMJSIDKUSA-N154.251154.012220944C00265(2r,3r)-1,4-dimercaptobutane-2,3-diol;1,4-dithiothreitol;2,3-dihydroxy-1,4-dithiobutane;Dl-threo-1,4-dimercapto-2,3-butanediol;L-dtt;L-threo-1,4-dimercapto-2,3-butanediol;Threo-1,4-dimercapto-2,3-butanediolPW_C008509L-DTT4561187922513012128212512385313640101Oxidized dithiothreitolHMDB0059664Oxidized dithiothreitol, also known as dithiane diol, belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres. Oxidized dithiothreitol is soluble (in water) and a very weakly acidic compound (based on its pKa). In humans, oxidized dithiothreitol is involved in the vitamin K metabolism pathway. Oxidized dithiothreitol is part of the Ubiquinone and other terpenoid-quinone biosynthesis pathway. It is a substrate for: Vitamin K epoxide reductase complex subunit 1.51621-02-4C0111943940742147388524DB01822O[C@H]1CSSC[C@@H]1OC4H8O2S2InChI=1S/C4H8O2S2/c5-3-1-7-8-2-4(3)6/h3-6H,1-2H2/t3-,4-/m0/s1YPGMOWHXEQDBBV-IMJSIDKUSA-N152.235151.99657088PW_C040101Oxidith455918792231301212801251238511361420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851316Carbon 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_C001316CO250812112044480135031864036773169520806511334316384917452255117314470528310353201115750108577110159681006026155607816164711786637107692219070171607035163706118871632057308198733321374612227530210821522582231519158249118492771190817012464226126882904262631543523318769942937712213377170132774703337773911277750129777633417807713478405356784273347894133179227130800083688067511980717135948363841132913911155491211199544061200891221201554071203644121205564141208334191209221241209914081212841251215053831227441201230114461231904501234184551234891181235563741238551361240633981253444791254602971255164811258244901258702991259314821262804801268875011270522061272775071273313881273905021407981851065OxygenHMDB0001377Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).7782-44-7C0000797715379CPD-6641952O=OO2InChI=1S/O2/c1-2MYMOFIZGZYHOMD-UHFFFAOYSA-N31.998831.989829244FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391561Peptidyl-4-carboxyglutamateCompoundCompoundPW_EC000561C06246KEGG CompoundP4C562Peptidyl-glutamateCompoundCompoundPW_EC000562C06247KEGG CompoundPG1543NAD(P)H dehydrogenase [quinone] 1P15559The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
HMDBP01689NQO116q22.1J0393411.6.5.21613294004846893114582521545Vitamin K-dependent gamma-carboxylaseP38435Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
HMDBP01691GGCX2p12AK29739714.1.1.90498261473311663292529154566188487101852Vitamin K epoxide reductase complex subunit 1Q9BQB6Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
HMDBP02242VKORC116p11.2AK28979011.17.4.45112616622930721045621814134015440NAD(P)H dehydrogenase [quinone] 11PW_P000440463154322119641160729129Vitamin K-dependent gamma-carboxylase1PW_P0001291471545146Vitamin K epoxide reductase complex subunit 11PW_P0001461641852180267PW_R180267Right68061019241Compoundfalse68063011441Compoundfalse680631400341Compoundfalse680611579151Compoundfalse6806327211Compoundfalse1701174401.6.5.2180270PW_R180270Right68062517461Compoundfalse68062685091Compoundfalse68062719241Compoundfalse680628401011Compoundfalse68062914201Compoundfalse170120146180268PW_R180268Right6806125611ElementCollectionfalse680613579151Compoundfalse68061413161Compoundfalse68061510651Compoundfalse6806165621ElementCollectionfalse68061717461Compoundfalse68061814201Compoundfalse1701181292592964299false84094010regular10025269617462981false1170160510regular200190268588419243181false28589310regular200190268588511443160false72589810regular50302685886400343155false62183810regular78782685887579153181false117089010regular20019026858887213159false101089510regular5030268588985091881false850142010regular2001902685890401011881false457141810regular200190268589114201849false517175410regular7878268590013161852false1139123110regular7878268590110651865false1112132110regular7878268590214201849false1097151610regular7878155985613718false1325124512regular10090155995623718false1330148512regular100909711543316false8109458subunitregular1608053011545182false119514048subunitregular150709515351852182false68116668subunitregular15070917440572996497142025923827Cofactor432812957185273530180561314657189473319515353827M760 1008 L830 1103 L868 1005 z10true183672568M485 988 C515 988 780 985 810 985 5false183672569M750 928 C750 984 780 985 810 985 5false183672570M660 916 C661 994 780 985 810 985 5false183672571M1170 985 C1140 985 1000 985 970 985 5false18trueM 241.94685504416483 649.261556296296 L 227 648 L 233.38088772118584 661.5751343230784false3672572M1035 925 C1034 981 1000 985 970 985 5false18trueM 241.94685504416483 649.261556296296 L 227 648 L 233.38088772118584 661.5751343230784false3672573M1170 1700 C1085 1699 994 1699 831 1701 5false183672574M950 1610 C952 1677 889 1702 831 1701 5false183672575M385 1083 C386 1166 388 1596 388 1702 C459 1702 600 1701 681 1701 5false18trueM 142.94685504416483 611.261556296296 L 128 610 L 134.38088772118584 623.5751343230784false3672576M557 1608 C560 1703 598 1702 681 1701 5false18trueM 142.94685504416483 611.261556296296 L 128 610 L 134.38088772118584 623.5751343230784false3672577M556 1754 C558 1702 633 1701 681 1701 5false18trueM 142.94685504416483 611.261556296296 L 128 610 L 134.38088772118584 623.5751343230784false3672595M1270 1080 C1271 1184 1270 1374 1270 1404 5false183672596M1217 1270 C1261 1271 1269 1300 1270 1404 5false183672597M1190 1360 C1236 1358 1269 1375 1270 1404 5false183672598M1270 1605 C1269 1551 1270 1504 1270 1474 5false18trueM 476.94685504416486 1358.261556296296 L 462 1357 L 468.38088772118584 1370.5751343230784false3672599M1175 1555 C1240 1551 1270 1504 1270 1474 5false18trueM 476.94685504416486 1358.261556296296 L 462 1357 L 468.38088772118584 1370.5751343230784false3672600M1325 1300 C1252 1300 1270 1374 1270 1404 5false183672601M1330 1540 C1289 1539 1270 1504 1270 1474 5false18trueM 476.94685504416486 1358.261556296296 L 462 1357 L 468.38088772118584 1370.5751343230784false7997255718026731323149926858843672568Left323150026858853672569Left323150126858863672570Left323150226858873672571Right323150326858883672572Right7552451701179177997265718027018323150426963672573Left323150526858893672574Left323150626858843672575Right323150726858903672576Right323150826858913672577Right7552461701208056137997305718026818323152226858873672595Left323152326859003672596Left323152426859013672597Left323152526963672598Right323152626859023672599Right14533155983672600Left14534155993672601Right755250170118432812772635903.13.10292001451286667020251.51.5-102328036018721039519911.61.60214327267479581111022700.80.8-3021490240183M276 1274 C276 1224 326 1174 376 1174 C679 1174 1072 1174 1375 1174 C1425 1174 1475 1224 1475 1274 C1475 1431 1475 1636 1475 1793 C1475 1843 1425 1893 1375 1893 C1072 1893 679 1893 376 1893 C326 1893 276 1843 276 1793 C276 1636 276 1431 276 1274 91true61199.0719.0685M124 770 C124 720 174 670 224 670 C618 670 1131 670 1525 670 C1575 670 1625 720 1625 770 C1625 1302 1625 1992 1625 2524 C1625 2574 1575 2624 1525 2624 C1131 2624 618 2624 224 2624 C174 2624 124 2574 124 2524 C124 1992 124 1302 124 770 1true61501.01954.0678235Liver715165201.61.620015679235Cytosol250730201.31.320015680235Extracellular Space820585201.01.020015681235Endoplasmic reticulum4201110201.61.620015890792235Hepatic Cell225615201.31.320015890793235Lumen6151258201.31.320015648393249759716492650441552205365968217324911461501192041#FFEEDE41252774