113168PathwayKandutsch-Russell Pathway (Cholesterol Biosynthesis)The Kandutsch-Russell pathway is the alternative pathway stemming from the mevalonate pathway completing cholesterol biosynthesis. The Bloch pathway and the Kandutsch-Russell pathway are both key to a functioning human body as cholesterol aids in the development of many important nutrients and hormones, such as vitamin D. Starting in the endoplasmic reticulum, lanosterol is the first compound used in this pathway, and when catalyzed by delta(24)-sterol-reductase, becomes 24,25-dihydrolanosterol. 24,25-Dihydrolanosterol is quickly converted to 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8-en-3b-ol with the help of the enzyme lanosterol 14-alpha demethylase. This same enzyme, lanosterol 14-alpha demethylase, is also responsible for the conversion of 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8-en-3b-ol into 4,4-dimethyl-14a-formyl-5a-cholest-8-en-3b-ol. Lanosterol 14alpha demethylase is used once more here, to push the pathway into the inner nuclear membrane, converting 4,4-dimethyl-14a-formyl-5a-cholest-8-en-3b-ol into 4,4-dimethyl-5a-cholesta-8,14-dien-3b-ol. Now located in the inner nuclear membrane, 4,4-dimethyl-5a-cholesta-8,14-dien-3b-ol is converted into 4,4-dimethyl-5a-cholesta-8-en-3b-ol through the help of a lamin-b receptor. Entering the endoplasmic reticulum membrane, methylsterol monooxygenase 1 is used to convert 4,4-dimethyl-5a-cholesta-8-en-3b-ol into 4a-hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol. 4a-Hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol then uses methylsterol monooxygenase 1 to become 4a-formyl-4b-methyl-5a-cholesta-8-en-3b-ol. Once again, methylsterol monooxygenase 1 is used to convert 4a-formyl-4b-methyl-5a-cholesta-8-en-3b-ol into 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol. Now using sterol-4-alpha-carboxylate 3-dehydrogenase, 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol is turned into 4a-methyl-5a-cholesta-8-en-3-one. This puts the pathway in the cell membrane, where a 3-keto-steroid reductase is used to convert 4a-methyl-5a-cholesta-8-en-3b-one into 4a-methyl-5a-cholesta-8-en-3-ol. Moving back into the endoplasmic reticulum membrane, methylsterol monooxygenase 1 converts 4a-methyl-5a-cholesta-8-en-3-ol into 4a-hydroxymethyl-5a-cholesta-8-en-3b-ol. Methylsterol monooxygenase is used twice more in this pathway, first converting 4a-hydroxymethyl-5a-cholesta-8-en-3b-ol into 4a-formyl-5a-cholesta-8-en-3b-ol, then converting 4a-formyl-5a-cholesta-8-en-3b-ol into 4a-carboxy-5a-cholesta-8-en-3b-ol. Now using sterol-4-alpha-carboxylate 3 dehydrogenase, 4a-carboxy-5a-cholesta-8-en-3b-ol becomes 5a-cholesta-8-en-3-one and brings the pathway back to the cell membrane. 5a-Cholesta-8-en-3-one teams up with a 3-keto-steroid reductase to create 5a-cholest-8-en-3b-ol. Then, stepping back into the endoplasmic reticulum membrane, 5a-cholest-8-en-3b-ol enlists the help of 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase to produce lathosterol. Lathosterol and lathosterol oxidase work together to make 7-dehydrocholesterol . Finally, 7-dehydrocholesterol partners with 7-dehydrocholesterol reductase to create cholesterol, completing the final step in cholesterol biosynthesis.MetabolicPW122328CenterPathwayVisualizationContext12260441004050#000099PathwayVisualization113031113168Kandutsch-Russell Pathway (Cholesterol Biosynthesis)The Kandutsch-Russell pathway is the alternative pathway stemming from the mevalonate pathway completing cholesterol biosynthesis. The Bloch pathway and the Kandutsch-Russell pathway are both key to a functioning human body as cholesterol aids in the development of many important nutrients and hormones, such as vitamin D. Starting in the endoplasmic reticulum, lanosterol is the first compound used in this pathway, and when catalyzed by delta(24)-sterol-reductase, becomes 24,25-dihydrolanosterol. 24,25-Dihydrolanosterol is quickly converted to 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8-en-3b-ol with the help of the enzyme lanosterol 14-alpha demethylase. This same enzyme, lanosterol 14-alpha demethylase, is also responsible for the conversion of 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8-en-3b-ol into 4,4-dimethyl-14a-formyl-5a-cholest-8-en-3b-ol. Lanosterol 14alpha demethylase is used once more here, to push the pathway into the inner nuclear membrane, converting 4,4-dimethyl-14a-formyl-5a-cholest-8-en-3b-ol into 4,4-dimethyl-5a-cholesta-8,14-dien-3b-ol. Now located in the inner nuclear membrane, 4,4-dimethyl-5a-cholesta-8,14-dien-3b-ol is converted into 4,4-dimethyl-5a-cholesta-8-en-3b-ol through the help of a lamin-b receptor. Entering the endoplasmic reticulum membrane, methylsterol monooxygenase 1 is used to convert 4,4-dimethyl-5a-cholesta-8-en-3b-ol into 4a-hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol. 4a-Hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol then uses methylsterol monooxygenase 1 to become 4a-formyl-4b-methyl-5a-cholesta-8-en-3b-ol. Once again, methylsterol monooxygenase 1 is used to convert 4a-formyl-4b-methyl-5a-cholesta-8-en-3b-ol into 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol. Now using sterol-4-alpha-carboxylate 3-dehydrogenase, 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol is turned into 4a-methyl-5a-cholesta-8-en-3-one. This puts the pathway in the cell membrane, where a 3-keto-steroid reductase is used to convert 4a-methyl-5a-cholesta-8-en-3b-one into 4a-methyl-5a-cholesta-8-en-3-ol. Moving back into the endoplasmic reticulum membrane, methylsterol monooxygenase 1 converts 4a-methyl-5a-cholesta-8-en-3-ol into 4a-hydroxymethyl-5a-cholesta-8-en-3b-ol. Methylsterol monooxygenase is used twice more in this pathway, first converting 4a-hydroxymethyl-5a-cholesta-8-en-3b-ol into 4a-formyl-5a-cholesta-8-en-3b-ol, then converting 4a-formyl-5a-cholesta-8-en-3b-ol into 4a-carboxy-5a-cholesta-8-en-3b-ol. Now using sterol-4-alpha-carboxylate 3 dehydrogenase, 4a-carboxy-5a-cholesta-8-en-3b-ol becomes 5a-cholesta-8-en-3-one and brings the pathway back to the cell membrane. 5a-Cholesta-8-en-3-one teams up with a 3-keto-steroid reductase to create 5a-cholest-8-en-3b-ol. Then, stepping back into the endoplasmic reticulum membrane, 5a-cholest-8-en-3b-ol enlists the help of 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase to produce lathosterol. Lathosterol and lathosterol oxidase work together to make 7-dehydrocholesterol . Finally, 7-dehydrocholesterol partners with 7-dehydrocholesterol reductase to create cholesterol, completing the final step in cholesterol biosynthesis.Metabolic1109693113163SubPathway27974523696639Sharpe LJ, Brown AJ: Controlling cholesterol synthesis beyond 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCR). J Biol Chem. 2013 Jun 28;288(26):18707-15. doi: 10.1074/jbc.R113.479808. Epub 2013 May 21.113168Pathway27974627697512 Prabhu AV, Luu W, Li D, Sharpe LJ, Brown AJ: DHCR7: A vital enzyme switch between cholesterol and vitamin D production. Prog Lipid Res. 2016 Oct;64:138-151. doi: 10.1016/j.plipres.2016.09.003. Epub 2016 Sep 30.113168Pathway1CellCL:00000004CardiomyocyteCL:00007465HepatocyteCL:00001823NeuronCL:000054012AstrocyteCL:00001272Platelet CL:00002337Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote17Rattus norvegicus10116EukaryoteRat5Bos taurus9913EukaryoteCattle10Drosophila melanogaster7227EukaryoteFruit fly2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia4202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum49Bathymodiolus platifrons220390EukaryoteDeep sea mussel19Schizosaccharomyces pombe4896Eukaryote5CytoplasmGO:00057372MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:00057894PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057831CytosolGO:000582910Cell MembraneGO:000588619Sarcoplasmic ReticulumGO:001652935ChloroplastGO:00095073Mitochondrial MatrixGO:000575936MembraneGO:001602032Inner MembraneGO:007025811Extracellular SpaceGO:000561512Mitochondrial Inner MembraneGO:000574314Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:00003256LysosomeGO:000576416Lysosomal LumenGO:004320220Endoplasmic Reticulum LumenGO:000578839Mitochondrial membraneGO:003196618Melanosome MembraneGO:003316225Golgi ApparatusGO:000579421SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:00057901LiverBTO:00007597295cardiocyteBTO:000153928StomachBTO:0001307155268Blood VesselBTO:0001102741124BrainBTO:000014289162Endothelium BTO:00003934Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273106KidneyBTO:00006717183Sympathetic Nervous SystemBTO:000183216SkinBTO:0001253154258511PW_BS0000083211PW_BS000003101711PW_BS0000105411PW_BS000005181311PW_BS0000182111PW_BS00000229111PW_BS00002949711PW_BS000049311511PW_BS00003114101PW_BS0000141115121PW_BS00011110813PW_BS0001081471241PW_BS00014715924PW_BS0001593551914PW_BS000035117131PW_BS000117188118PW_BS0000241632181PW_BS000163205561PW_BS0000241601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS0001702253541PW_BS000024151141PW_BS000151224241PW_BS0000241985181PW_BS0000242111018PW_BS000024222341PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS000024315123PW_BS0000243221231PW_BS00002429341PW_BS0000241321121PW_BS0001323317121PW_BS00002833217121PW_BS00002813013121PW_BS0001301122121PW_BS0001121151012PW_BS0001153361121PW_BS0000281192171PW_BS000119943PW_BS000094407251PW_BS000115405105PW_BS000115122551PW_BS0001221231751PW_BS0001231251351PW_BS000125429151PW_BS000115124151PW_BS000124383751PW_BS0001003761017PW_BS0000531355171PW_BS00013544717171PW_BS00011513613171PW_BS0001364641171PW_BS0001151181171PW_BS0001183987171PW_BS0001134812101PW_BS0001152975101PW_BS0000242991101PW_BS0000244957101PW_BS000115206261PW_BS000024388161PW_BS000112390761PW_BS000112168321PW_BS0001684311PW_BS00000415111PW_BS000015261115PW_BS000026541315PW_BS000054171211PW_BS000017221411PW_BS000022422411PW_BS0000427028511PW_BS000070103331PW_BS000103107313PW_BS000107100521PW_BS000100105113PW_BS0001051553241PW_BS0001551572241PW_BS0001571613181PW_BS00016116611PW_BS0001661783211PW_BS00017815284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS00002416212181PW_BS0001621951318PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS0000242231241PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS0000241333121PW_BS00013313412121PW_BS0001341141112PW_BS00011432711125PW_BS00002834713125PW_BS00002834524121PW_BS0000283683601PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109406351PW_BS000115409115PW_BS0001154241155PW_BS0001154251355PW_BS0001154182451PW_BS0001153841251PW_BS0001001203171PW_BS0001201371117PW_BS00013745911175PW_BS00011546013175PW_BS00011545424171PW_BS00011512112171PW_BS0001214793101PW_BS0001154831110PW_BS00011548924101PW_BS00011548012101PW_BS00011530013101PW_BS000024501361PW_BS000115208116PW_BS0000245062461PW_BS0001153911261PW_BS0001123951361PW_BS00011388231202PW_BS00055288312021PW_BS000552167311PW_BS000167788241113PW_BS00052459724112PW_BS000336185321PW_BS0000243344121PW_BS000028408451PW_BS0001153744171PW_BS0000534824101PW_BS000115502461PW_BS0001159611PW_BS0000092811611PW_BS0000285811411PW_BS0000583612011PW_BS00003613121PW_BS0000136131PW_BS0000061021231PW_BS000102126651PW_BS00012612711651PW_BS00012715612241PW_BS00015611PW_BS00000117912211PW_BS0001792164181PW_BS0000242156181PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000241136121PW_BS000113337116121PW_BS00002832914121PW_BS0000283583912PW_BS00002836912601PW_BS0000283821451PW_BS0001004436171PW_BS000115448116171PW_BS00011539914171PW_BS00011348414101PW_BS000115207661PW_BS000024209106PW_BS0000243891461PW_BS0001121861221PW_BS00002416212PW_BS000016204111PW_BS000020331811PW_BS0000332441011PW_BS00002429817101PW_BS00002412915121PW_BS00012934141121PW_BS00002834318121PW_BS000028360410121PW_BS0000284141551PW_BS0001154151851PW_BS00011543441051PW_BS00011545015171PW_BS00011545118171PW_BS000115469410171PW_BS0001154781010PW_BS0001155041861PW_BS00011551541061PW_BS000115432511PW_BS00004360251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS000110140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS0000951802211PW_BS00018021425181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS000024253541PW_BS0000243331212PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154192551PW_BS000115436255PW_BS0001154461217PW_BS00011545525171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155072561PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS000549111811PW_BS00001114117191PW_BS00014178811PW_BS000078193513PW_BS0000195311015PW_BS0000539731715PW_BS000569104716711PW_BS000577146NADPHHMDB0000221Nicotinamide 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_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139014070616840034Hydrogen 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039514069288214069388314069916714070716814071514140742788140743597140760185966LanosterolHMDB0001251Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide.(wikipedia).79-63-0C0172424698316521LANOSTEROL216175[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)CC30H50OInChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1CAHGCLMLTWQZNJ-BQNIITSRSA-N426.7174426.386166222FDB013802(3 beta)-lanosta-8,24-dien-3-ol;(3alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;(3beta)-lanosta-8,24-dien-3-ol;(3beta,5alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;4,4',14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol;Botalan base 138;Lanosta-8,24-dien-3-ol;Lanosta-8,24-dien-3beta-ol;Lanosta-8,24-dienol;Lanosterin;Lanosterol;Lanster;(3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol;(3b)-lanosta-8,24-dien-3-ol;(3β)-lanosta-8,24-dien-3-olPW_C000966Lastrol82718162487322198761416082862107893111112149112212404913514070049143NADPHMDB0000217Nicotinamide 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_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390140709168296224,25-DihydrolanosterolHMDB000683924,25-Dihydrolanosterol, also known as lanostenol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 24,25-dihydrolanosterol is considered to be a sterol lipid molecule. 24,25-Dihydrolanosterol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 24,25-dihydrolanosterol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 24,25-dihydrolanosterol is involved in the simvastatin action pathway, the atorvastatin action pathway, the alendronate action pathway, and the ibandronate action pathway. 24,25-Dihydrolanosterol is also involved in several metabolic disorders, some of which include the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the cholesteryl ester storage disease pathway, the mevalonic aciduria pathway, and lysosomal acid lipase deficiency (wolman disease). Outside of the human body, 24,25-dihydrolanosterol can be found in a number of food items such as yellow bell pepper, orange bell pepper, green bell pepper, and red bell pepper. This makes 24,25-dihydrolanosterol a potential biomarker for the consumption of these food products. 24,25-Dihydrolanosterol is involved in the biosynthesis of steriods. 24,25-Dihydrolanosterol is reversibly converted to lanosterol by delta24-sterol reductase [EC:1.3.1.72].79-62-9C0510944056028113CPD-8606389460[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C30H52OInChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1MBZYKEVPFYHDOH-BQNIITSRSA-N428.7333428.401816286FDB004614LanostenolPW_C0029622425Di162649732321378932331121493383124051398964FADHMDB0001248FAD, 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_C000964FAD9991145186819232164253176282882518840211881414894216122916224921335825362237232646023646883147411347581048816526810352851025335111549612655111275613118603015560541566082161611616263901647517864991796666107703916371752057321213746522274872239076224118182161188721511899211122962251232824912443151125192271259522612710291127202921302930113041302436233187708029377126133771521347750111377507112775181157754133477615132777263377805432978375345789303317922233679272358800123688003436980714119119958406119999384120051408120107407120432405120453122120490124121278429121298418121417382121489383122748120122776121122802374122823443123066376123087135123166448123849464123868454123976399124047398125348479125378480125429482125474481125697297125979489126107299126277484126891501126920391126968502126987207127011206127310209127432506127602388127840389140790185140799186891FMNH2HMDB0001142FMNH2 is the reduced form of flavin mononucleotide. It is a substrate of the enzyme FMN reductase (EC 1.5.1.29), an enzyme that catalyzes the chemical reaction FMNH2 + NAD(P)+ <=> FMN + NAD(P)H + H+. Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase. During a catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH•) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers.5666-16-0C0184744539516048FMNH2393046CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1C17H23N4O9PInChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/t11-,12+,14-/m0/s1YTNIXZGTHTVJBW-SCRDCRAPSA-N458.3597458.120264866FDB022449Fmnh2;Reduced fmn;Reduced flavin mononucleotide;1,5-dihydroriboflavin 5'-(dihydrogen phosphate);Flavin mononucleotide (reduced);Fmnh;1,5-dihydroriboflavin 5'-(dihydrogen phosphoric acid)PW_C000891FMNH211954225140701491065OxygenHMDB0001377Oxygen 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_C001065O29591105245165001850585491462528638364910674316882075415763476933836213754920162425312228032942604247471354671235480125549312655081275809108597314761291597006188703216370501607319213753321075602128395151118162161186419811883215118942111205722512063164122472861227922612325249127062911271629213004298130163001302630113038302132602234227617426573157691029377044294772141347735011177363130773773317739533277497113775121157753733477626336777233377773611277747129777563417780511477812133780703297815113278381345788053437911136012004740812038312212042640512054240712055341412059440912060140612088341512104512412110438312160543412165642912211738212257341812268938412279837412282244312302713512306037612312844712313913612316344812317611912318745012321913712322612012345945112360911812366939812416346912421446412466939912514545412527512112542548212570647812573148312573729712574047912588448112610029912627248412652249512672148912682548012696450212698620712719820912721420812721920512722250112730550412734520612755738812757451512783538912808139512809539012831250612843239192Formic acidHMDB0000142Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.64-18-6C000581897100230751FORMATE278DB01942OC=OCH2O2InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYSA-N46.025446.005479308DBMET00489FDB012804Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600lPW_C000092Formate94689773162949194325314111534811266361077158205718620673252137616160828721011982151435223187696322578652132789343311206701221206974071214963831217511241232841351233021191240543981243021181257532971257724811264782991268214951276373881284263901170Flavin MononucleotideHMDB0001520Flavin mononucleotide (FMN), or riboflavin-5?-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.146-17-8C0006164397617621FMN559060DB03247CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2C17H21N4O9PInChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1FVTCRASFADXXNN-SCRDCRAPSA-N456.3438456.104614802FDB001984Fmn;Flanin;Flavine mononucleotide;Flavol;Riboflavin;Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate;Riboflavin mononucleotide;Riboflavin monophosphate;Riboflavin phosphate;Riboflavin-5'-phosphate na;Riboflavin-5-phosphate;Riboflavine 5'-monophosphate;Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate;Riboflavine monophosphate;Riboflavine phosphate;Riboflavine-5'-phosphate;Vitamin b2 phosphate;Flavin mononucleotide;Riboflavin 5'-(dihydrogen phosphate)PW_C001170FlvnMnt53981190141692249613157721011190021112313225775191157759011178730132120433405120454122121929124123067376123088135124482118125698297126104299127190205127312209127686388140703491420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851046564,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol4,4-Dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol has the chemical formula C30H52O2, and an average molecular weight of 444.744. 4,4-Dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol is involved in the Kandutsch-Russell Pathway (Cholesterol Biosynthesis).1569882187057CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(CO)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3C30H52O2InChI=1S/C30H52O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h20-22,25-26,31-32H,8-19H2,1-7H3/t21-,22-,25+,26+,28-,29-,30-/m1/s1SJPDNXKPBQHPMZ-PUXRVUTHSA-N444.744444.396730914PW_C10465644DH5C81799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L616.487616.177297665FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911046574,4-Dimethyl-14α-formyl-5α-cholest-8-en-3β-ol4,4-Dimethyl-14α-formyl-5α-cholest-8-en-3β-ol has the chemical formula C30H50O2, and an average molecular weight of 442.728. 4,4-Dimethyl-14α-formyl-5α-cholest-8-en-3β-ol is involved in the Kandutsch-Russell Pathway (Cholesterol Biosynthesis).1569882487060CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3C30H50O2InChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h19-22,25-26,32H,8-18H2,1-7H3/t21-,22-,25+,26+,28-,29-,30-/m1/s1MKMLAQLNFVFNRK-PUXRVUTHSA-N442.728442.38108085PW_C10465744DF5C81046584,4-Dimethyl-5α-cholesta-8,14-dien-3β-ol4,4-dimethylcholesta-8,14-dien-3-ol
167817CC(C)CCC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3C29H48OInChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h13,19-20,22,25-26,30H,8-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1OGQJUYXFIOFTMA-PBJLWWPKSA-N412.702412.3705161664,4-dimethylcholesta-8,14-dien-3-olPW_C10465844DCdol29634,4-Dimethyl-5a-cholesta-8-en-3b-olHMDB00068404,4-Dimethyl-5a-cholesta-8-en-3b-ol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8-en-3b-ol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 4,4-dimethyl-5a-cholesta-8-en-3b-ol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 4,4-dimethyl-5a-cholesta-8-en-3b-ol is involved in steroid biosynthesis pathway, the alendronate action pathway, the risedronate action pathway, and the simvastatin action pathway. 4,4-Dimethyl-5a-cholesta-8-en-3b-ol is also involved in several metabolic disorders, some of which include the hypercholesterolemia pathway, the wolman disease pathway, lysosomal acid lipase deficiency (wolman disease), and the smith-lemli-opitz syndrome (slos) pathway. 4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is involved in the biosynthesis of steriods. 4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is reversibly converted into 14-Demethyllanosterol by delta24-sterol reductase [EC:1.3.1.72].C159152372460430792004[H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C29H50OInChI=1S/C29H50O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h19-20,22-23,25-26,30H,8-18H2,1-7H3/t20-,22-,23?,25+,26+,28-,29-/m1/s1FYHRVINOXYETMN-HFPXORMNSA-N414.7067414.386166222FDB0241133beta-hydroxy-4,4-dimethyl-8(9)-cholestene;3beta-hydroxy-4,4-dimethylcholest-8(9)-ene;4,4-dimethyl-3beta-hydroxy-8(9)-cholestene;4,4-dimethyl-3beta-hydroxycholest-8(9)-ene;4,4-dimethyl-5alpha-cholesta-8-en-3beta-ol;4,4-dimethylcholest-8(9)-en-3beta-ol;4,4-dimethylcholesta-8(9)-en-3beta-olPW_C00296344DCBol163349732821378936331121500383124058398544Fe2+HMDB0000692Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.15438-31-0C148182728429033Ferric-Hydroxamate-Complexes25394DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133FDB016251Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)PW_C000544Fe2+39819641367831692207098177727041163705216012060225121431517717913277740112777511297776034177782111120544407120557414120570122121765124123178119123191450123204135124316118126143299126185481127650388140710491407161877264α-Hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-olHMDB00121714alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic oxidation of 4,4-dimethyl-5alpha-cholesta-8-en-3-beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25203709CPD-8611CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO)C1CC3C29H50O2InChI=1S/C29H50O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h19-20,22-23,25-26,30-31H,7-18H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1UVSRXDFMOZKKGE-AEWFMJFUSA-N430.7061430.3810808444a-hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol;4a-hydroxymethyl-4beta-methyl-5a-cholesta-8-en-3beta-ol;4alpha-hydroxymethyl-4b-methyl-5alpha-cholesta-8-en-3b-olPW_C007726HbMCeol8133Fe3+HMDB0012943Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.20074-52-6C148192993629034CPD-1013427815[Fe+3]FeInChI=1S/Fe/q+3VTLYFUHAOXGGBS-UHFFFAOYSA-N55.84555.934942133C14819Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))PW_C008133Fe3+1230312968142049199727042163118411601267515177431111774503317859911278721132120949407121013122121127383121593124123515119123578135123696398124151118125890481127351206127559388140718189794IronHMDB0015531Iron is a metallic element found in certain minerals, in nearly all soils, and in mineral waters. Iron is required for life. It exists in all living species, ranging from bacteria to humans. It can be found primarily in blood and it is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. In humans, iron is involved in several metabolic pathways, some of which include the rofecoxib pathway, magnesium salicylate action pathway, etodolac pathway, and diclofenac pathway. Iron is also involved in several metabolic disorders, some of which include adenine phosphoribosyltransferase deficiency (APRT), porphyria variegata (PV), adenylosuccinate lyase deficiency, and AICA-ribosiduria. The major activity of supplemental iron is in the prevention and treatment of iron-deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic, and cognition-enhancing activities. Iron can be found in a number of food items such as chinese water chestnut, hyssop, daikon radish, and peppermint, which makes it a potential biomarker for the consumption of these food products.7439-89-6C00023239251824822368DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133C0002326fe;Eisen;Fe;Fer;Ferrum;HierroPW_C009794Iron11388126651533216354931192943411873302131205622577683130779283367826113278409111784283347893833112083812212099240812125642912137112412150238312172712512342313512355737412382646412393011812406039812427813612582929712593248212604429912728220512739150212749638877234α-Formyl-4β-methyl-5α-cholesta-8-en-3β-olHMDB00121684alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic oxidation of 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25201774CPD-8612CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC3C29H48O2InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h18-20,22-23,25-26,31H,7-17H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1WWTBBRMTEFBUND-AEWFMJFUSA-N428.6902428.365430784a-formyl-4b-methyl-5a-cholesta-8-en-3b-ol;4a-formyl-4beta-methyl-5a-cholesta-8-en-3beta-ol;4alpha-formyl-4b-methyl-5alpha-cholesta-8-en-3b-olPW_C007723fmceol77204α-Carboxy-4β-methyl-5α-cholesta-8-en-3β-olHMDB00121654alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol. It is also a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and can be generated from the enzymatic carboxylation of 4alpha-methyl-5alpha-cholesta-8-en-3-one. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25202944CPD-8613CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=OC29H48O3InChI=1S/C29H48O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h18-19,21-22,24-25,30H,7-17H2,1-6H3,(H,31,32)/t19?,21?,22?,24?,25-,27+,28+,29-/m0/s1GLCDBDRQLZKKOJ-XQTRBMGCSA-N444.6896444.3603454024a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol;4a-carboxy-4beta-methyl-5a-cholesta-8-en-3beta-ol;4alpha-carboxy-4b-methyl-5alpha-cholesta-8-en-3b-olPW_C007720CMCEOL1046594α-methyl-5α-cholesta-8-en-3-ol4α-methyl-5α-cholesta-8-en-3-ol has the chemical formula C28H48O, and an average molecular weight of 400.691. 4α-methyl-5α-cholesta-8-en-3-ol is involved in the Kandutsch-Russell Pathway (Cholesterol Biosynthesis).C05110645264087051CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@@H]1CC3C28H48OInChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24,26,29H,7-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1SCEZIHJVTBQOLS-YIJYGBTNSA-N400.691400.370516166Methost-8-enolPW_C104659M8E77284α-hydroxymethyl-5α-cholesta-8-en-3β-olHMDB00121734Alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4a-formyl-5a-cholesta-8-en-3b-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25201885CPD-8607CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC3C28H48O2InChI=1S/C28H48O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h18-19,21-24,26,29-30H,6-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1UPEGTKGKNWDIAN-GYISYUOESA-N416.6795416.36543078PW_C007728hmceol77244α-Formyl-5α-cholesta-8-en-3β-olHMDB00121694alpha-formyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic reduction of 4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis II (via 24,25-dihydrolanosterol) may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25200885CPD-8618CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C=O)C1CC3C28H46O2InChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h17-19,21-24,26,30H,6-16H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1MHYWFGFPMGLYBL-GYISYUOESA-N414.6636414.3497807164a-formyl-5a-cholesta-8-en-3b-ol;4a-formyl-5a-cholesta-8-en-3beta-ol;4alpha-formyl-5alpha-cholesta-8-en-3b-olPW_C007724fceol77214α-Carboxy-5α-cholesta-8-en-3β-olHMDB00121664alpha-carboxy-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and it can be generated from the enzymatic carboxylation of 5alpha-cholesta-8-en-3-one. It is also a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25200718CPD-8619CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=OC28H46O3InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1RODBXVVNKJCWQR-KLZNZPMLSA-N430.663430.3446953384a-carboxy-5a-cholesta-8-en-3b-ol;4a-carboxy-5a-cholesta-8-en-3beta-ol;4alpha-carboxy-5alpha-cholesta-8-en-3b-olPW_C0077214C5C8E377335α-cholesta-8-en-3-oneHMDB00121785Alpha-cholesta-8-en-3-one is involved in the cholesterol biosynthesis II(via 24,25-dihydrolanosterol) pathway. It can be generated from the enzymatic reduction of 4a-methyl-cholesta-8-enol or enzymatic oxidation of 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol.The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25203379CPD-8614CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)CC1CC3C27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,23-24H,6-17H2,1-5H3/t19?,20?,23?,24?,26-,27+/m0/s1RZSXSHNNQBIPTL-HJWVNVQISA-N384.6377384.339216035a-cholesta-8-en-3-onePW_C0077335chene29645a-Cholest-8-en-3b-olHMDB00068415a-Cholest-8-en-3b-ol is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decrease and cholesterol precursor sterols such as zymostenol increase. (PMID: 15736111, 16709621, 16477216, 12756385).566-97-2C0384510177016608CPD-862191952[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1QETLKNDKQOXZRP-XTGBIJOFSA-N386.6535386.354866094FDB024114(3beta,5alpha)cholestenol;3beta-hydroxy-8(9)-cholestene;3beta-hydroxycholest-8(9)-ene;5alpha-cholest-8(9)-en-3beta-ol;5alpha-cholest-8-en-3beta-ol;Cholest-8(9)-en-3beta-ol;Cholesta-8(9)-en-3beta-ol;Delta(8)-cholestenol;5-alpha-cholest-8-en-3-beta-ol;Cholestenol;Zymostenol;5a-cholest-8-en-3b-ol;5α-cholest-8-en-3β-olPW_C0029645aChlol164549733721378947331121512383124070398908LathosterolHMDB0001170Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O.80-99-9C011896572817168CPD-418659151[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1IZVFFXVYBHFIHY-SKCNUYALSA-N386.6535386.354866094FDB022463(3beta)-cholest-7-en-3-ol;(3beta,5alpha)-cholest-7-en-3-ol;(3beta,alpha)-cholest-7-en-3-ol;(7)-cholestenol;3b-hydroxy-5-cholestene;3beta-hydroxy-5alpha-cholest-7-ene;5-a-cholest-7-en-3-beta-ol;5-alpha-cholest-7-en-3-beta-ol;5alpha-cholest-7-en-3beta-ol;7-cholesten-3-beta-ol;7-cholestenol;7-cholesterol;Cholest-7-en-3-ol;Cholest-7-en-3beta-ol;Cholest-7-en-ol;Cholesterol - synthetic;Cholesterol pharma;Cholesterol extra pure;Cholesterol gr;Cholesterol,nf grade;Delta7-cholesten-3beta-ol;Delta7-cholestenol;Lathosterol;Delta(7)-cholestenol;Gamma-cholestenol;Gamma-cholesterol;G-cholesterol;γ-cholesterolPW_C000908Lathost164849733821378948331121513383124071398227-DehydrocholesterolHMDB00000327-Dehydrocholesterol is a zoosterol (a sterol produced by animals rather than plants). It is a provitamin-D. The presence of this compound in skin enables humans to manufacture vitamin D3 from ultraviolet rays via an intermediate isomer provitamin D3. It is also found in breast milk.434-16-2C01164439423177597-DEHYDRO-CHOLESTEROL388534[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1UCTLRSWJYQTBFZ-DDPQNLDTSA-N384.6377384.33921603FDB021882(-)-7-dehydrocholesterol;(3b)-cholesta-5,7-dien-3-ol;(3beta)-cholesta-5,7-dien-3-ol;10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-ol;17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol;5,7-cholestadien-3-beta-ol;5,7-cholestandien-3-ol;5,7-cholestandien-3beta-ol;7,8-dehydro-cholesterol;7,8-didehydrocholesterol;7-dehydro-cholesterol;7-dehydrocholesterin;7-dehydrocholesterol;7dhc;Cholesta-5,7-dien-3 beta -ol;Cholesta-5,7-dien-3-beta-ol;Cholesta-5,7-dien-3-ol;Cholesta-5,7-dien-3b-ol;Cholesta-5,7-dien-3beta-ol;Dehydrocholesterin;Dehydrocholesterol;Delta5,7-cholestadien-3beta-ol;Delta5,7-cholesterol;Delta7-cholesterol;Provitamin d3;Provitamin-d3;5,7-cholestadien-3beta-ol;(3β)-cholesta-5,7-dien-3-olPW_C0000227DHC16554973402137895033112151538312407339847CholesterolHMDB0000067Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50% of the lipid in the membrane or 60-80% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginine (ADMA) in the endothelium since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with highly oxidized levels of LDL, pose a heightened risk factor for vascular disease. Chronically high levels of cholesterol are associated with at least five inborn errors of metabolism, including cerebrotendinous xanthomatosis, cholesteryl ester storage disease, congenital lipoid adrenal hyperplasia, hypercholesterolemia, and Zellweger syndrome. In chronically high levels, cholesterol can function as an atherogen (causes atherosclerosis and cardiovascular disease). Specifically, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease.57-88-5C00187599716113CHOLESTEROL5775DB04540[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1HVYWMOMLDIMFJA-DPAQBDIFSA-N386.6535386.354866094FDB013269(+)-ent-cholesterol;(-)-cholesterol;(20bfh)-cholest-5-en-3b-ol;(3b)-cholest-5-en-3-ol;(3beta)-cholest-5-en-3-ol;20-epi-cholesterol;20-iso-cholesterol;20bfh-cholest-5-en-3b-ol;3beta-hydroxycholest-5-ene;5-cholesten-3b-ol;5-cholesten-3beta-ol;5:6-cholesten-3-ol;5:6-cholesten-3beta-ol;Cholest-5-en-3-ol;Cholest-5-en-3b-ol;Cholest-5-en-3beta-ol;Cholesterin;Cholesterine;Cholesterol;Cholesterol base h;Cholesteryl alcohol;Cholestrin;Cholestrol;Cordulan;Dastar;Dusoline;Dusoran;Dythol;Epicholesterin;Epicholesterol;Fancol ch;Hydrocerin;Kathro;Lanol;Liquid crystal cn/9;Nimco cholesterol base h;Nimco cholesterol base no. 712;Super hartolan;TegolanPW_C000047Lanol8292165849233032840292845157341213756721076491607765333677685114789513317898811212151638312169742912173140912183140712407439812424646412428213712438411977294α-methyl-5α-cholesta-8-en-3-oneHMDB00121744Alpha-methyl-5alpha-cholesta-8-en-3-one is involved in the cholesterol biosynthesis II(via 24,25-dihydrolanosterol) pathway. It can be generated from the enzymatic reduction of 4A-methyl-cholesta-8-enol or enzymatic oxidation of 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol.The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25202835CPD-8614CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)C1CC3C28H46OInChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24H,7-17H2,1-6H3/t19?,20-,22?,23?,24?,27+,28-/m0/s1SDZUXFFGOQZLPK-RJBGAFQBSA-N398.6642398.3548660944a-methyl-5a-cholesta-8-en-3-onePW_C0077294M5C8E31316Carbon 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_C001316CO250812112044480135031864036773169520806511334316384917452255117314470528310353201115750108577110159681006026155607816164711786637107692219070171607035163706118871632057308198733321374612227530210821522582231519158249118492771190817012464226126882904262631543523318769942937712213377170132774703337773911277750129777633417807713478405356784273347894133179227130800083688067511980717135948363841132913911155491211199544061200891221201554071203644121205564141208334191209221241209914081212841251215053831227441201230114461231904501234184551234891181235563741238551361240633981253444791254602971255164811258244901258702991259314821262804801268875011270522061272775071273313881273905021407981851688Delta(24)-sterol reductaseQ15392Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
HMDBP01935DHCR241p32.3AF39833711.3.1.7216274913578518259Lanosterol 14-alpha demethylaseQ16850Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
HMDBP00265CYP51A17q21.2U5168711.14.13.701630491357861814268753142688973142760104722637Lamin-B receptorQ14739
Anchors the lamina and the heterochromatin to the inner nuclear membrane.
LBR1135777168257Methylsterol monooxygenase 1Q15800HMDBP00263MSMO14q32-q34BC01065311.14.13.72163649135780187933-keto-steroid reductaseP56937Responsible for the reduction of the keto group on the C-3 of sterols.
HMDBP00848HSD17B71q23AF16276111.1.1.270; 1.1.1.62164149135779148923-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
HMDBP00949EBPXp11.23-p11.22BC00154915.3.3.5164449130Lathosterol oxidaseO75845Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
HMDBP00135SC5DL11q23.3BC01233311.14.21.61660495207-dehydrocholesterol reductaseQ9UBM7Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
HMDBP00548DHCR711q13.4AF06248111.3.1.2113578249258Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingQ15738HMDBP00264NSDHLXq28BC00024511.1.1.17016394913578718441Delta(24)-sterol reductase1PW_P000441464168812129641442Lanosterol 14-alpha demethylase1PW_P00044246525912131799112856Lamin-B Receptor1PW_P01285622615226371135778168444Methylsterol monooxygenase 11PW_P0004444672571214979414463-keto-steroid reductase1PW_P00044646979314473-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase1PW_P0004474708921451Lathosterol oxidase1PW_P000451474130121597941128577-Dehydrodesmosterol reductase1PW_P01285722616520113578149445Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating1PW_P0004454682581179314PW_R179314Right6765331461Compoundfalse676534400341Compoundfalse6765359661Compoundfalse6765361431Compoundfalse67653729621Compoundfalse169219441179315PW_R179315Right67653829621Compoundfalse6765398913Compoundfalse67654010653Compoundfalse676541921Compoundfalse67654211703Compoundfalse67654314204Compoundfalse676544400341Compoundfalse6765451046561Compoundfalse169220442179316PW_R179316Right6765461046561Compoundfalse6765478913Compoundfalse67654810653Compoundfalse6765491046571Compoundfalse67655011703Compoundfalse67655114204Compoundfalse676552921Compoundfalse676553400341Compoundfalse169221442179317PW_R179317Right6765541046571Compoundfalse6765558913Compoundfalse67655610653Compoundfalse6765571046581Compoundfalse67655811703Compoundfalse676559921Compoundfalse67656014204Compoundfalse676561400341Compoundfalse169222442179318PW_R179318Right6765621046581Compoundfalse6765631461Compoundfalse676564400341Compoundfalse67656529631Compoundfalse6765661431Compoundfalse16922312856179319PW_R179319Right67656729631Compoundfalse6765685446Compoundfalse676569400345Compoundfalse67657010653Compoundfalse67657177261Compoundfalse67657281336Compoundfalse67657314204Compoundfalse169224444179320PW_R179320Right67657477261Compoundfalse6765755446Compoundfalse676576400345Compoundfalse67657710653Compoundfalse67657877231Compoundfalse67657981336Compoundfalse67658014204Compoundfalse169225444179321PW_R179321Right67658177231Compoundfalse6765825446Compoundfalse676583400345Compoundfalse67658410653Compoundfalse67658577201Compoundfalse67658681336Compoundfalse67658714204Compoundfalse169226444179324PW_R179324Right6765981046591Compoundfalse6765995446Compoundfalse676600400345Compoundfalse67660110653Compoundfalse67660277281Compoundfalse67660381336Compoundfalse67660414204Compoundfalse169229444179325PW_R179325Right67660577281Compoundfalse6766065446Compoundfalse676607400345Compoundfalse67660810653Compoundfalse67660977241Compoundfalse67661081336Compoundfalse67661114204Compoundfalse169230444179326PW_R179326Right67661277241Compoundfalse6766135446Compoundfalse676614400345Compoundfalse67661510653Compoundfalse67661677211Compoundfalse67661781336Compoundfalse67661814204Compoundfalse169231444179329PW_R179329Right67662929641Compoundfalse6766309081Compoundfalse169234447179330PW_R179330Right6766319081Compoundfalse6766325442Compoundfalse676633400342Compoundfalse67663410651Compoundfalse676635221Compoundfalse67663681331Compoundfalse67663714202Compoundfalse169235451179331PW_R179331Right676638221Compoundfalse6766391461Compoundfalse676640400341Compoundfalse676641471Compoundfalse6766421431Compoundfalse16923612857179322PW_R179322Right67658877201Compoundfalse6765891431Compoundfalse67659077291Compoundfalse6765911461Compoundfalse67659213161Compoundfalse169227445179323PW_R179323Right67659377291Compoundfalse6765941461Compoundfalse676595400341Compoundfalse6765961046591Compoundfalse6765971431Compoundfalse169228446179327PW_R179327Right67661977211Compoundfalse6766201431Compoundfalse67662177331Compoundfalse6766221461Compoundfalse676623400341Compoundfalse169232445179328PW_R179328Right67662477331Compoundfalse676625400341Compoundfalse6766261461Compoundfalse67662729641Compoundfalse6766281431Compoundfalse16923344626781001461862false120480010regular50302678101400341855false144077510regular787826781029661881false124456010regular20019026781031431861false1444102110regular5030267810429621881false1244109610regular2001902678105964189false129487920regular1002526781068911881false1044129610regular200190267810710651865false1441134710regular78782678108921881false1034172110regular200190267810911701881false1034152110regular200190267811014201849false1442167210regular78782678111400341855false1445155710regular787826781121046561881false1243183610regular20021026781131799189false1295144319regular1002526781148911881false1039200110regular200190267811510651865false1445205210regular787826781161046571881false1244250510regular200200267811711701881false1059223010regular200190267811814201849false1440224110regular78782678119921881false1468234010regular2001902678120400341855false1149243610regular787826781211799189false1294215519regular1002526781308911881false1039271210regular200190267813110651865false1440277210regular787826781321046581881false1254351210regular200200267813311701881false1049312210regular2001902678134921881false1444312210regular200190267813514201849false1425300710regular78782678136400341855false1195301010regular787826781371799189false1294289820regular10025267814214616862false1569349910regular503026781434003416855false1540368410regular78782678144296316881false2034351310regular200200267814514316861false1884370810regular503026781535444981false2233286310regular2001902678154400344955false1953284410regular7878267815510654965false1951295910regular7878267815677264981false2031237010regular200200267815781334981false1821255010regular200190267815814204949false2226260610regular787826781599794499false2081273919regular1002526781605444981false1820221010regular2001902678161400344955false1950211610regu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815 C1284 815 1343 815 1344 889 5false183657194M1440 814 C1396 815 1345 830 1344 889 5false183657195M1344 750 C1343 817 1344 803 1344 889 5false183657196M1444 1036 C1410 1035 1344 1041 1344 959 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657197M1344 1096 C1345 1014 1345 1076 1344 959 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657198M1289 809 L1289 859 L1339 809 z10true183657199M1344 1286 C1344 1316 1345 1423 1345 1453 5false183657200M1244 1391 C1290 1388 1344 1421 1345 1453 5false183657201M1441 1386 C1391 1384 1346 1411 1345 1453 5false183657202M1234 1816 C1282 1814 1344 1612 1345 1523 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657203M1234 1616 C1279 1615 1344 1575 1345 1523 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657204M1442 1711 C1386 1711 1344 1612 1345 1523 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657205M1445 1596 C1392 1597 1345 1584 1345 1523 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657206M1343 1836 C1343 1806 1345 1553 1345 1523 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3657207M1180 1338.5 L1180 1388.5 L1230 1338.5 z10true183657208M1343 2046 C1343 2076 1344 2135 1344 2165 5false183657209M1239 2096 C1272 2096 1344 2110 1344 2165 5false183657210M1445 2091 C1406 2090 1344 2106 1344 2165 5false183657211M1344 2505 C1344 2475 1344 2265 1344 2235 5false18trueM 25.946855044164835 1138.261556296296 L 11 1137 L 17.380887721185843 1150.5751343230784false3657212M1259 2325 C1312 2328 1344 2296 1344 2235 5false18trueM 25.946855044164835 1138.261556296296 L 11 1137 L 17.380887721185843 1150.5751343230784false3657213M1440 2280 C1413 2282 1343 2279 1344 2235 5false18trueM 25.946855044164835 1138.261556296296 L 11 1137 L 17.380887721185843 1150.5751343230784false3657214M1468 2435 C1404 2433 1346 2323 1344 2235 5false18trueM 25.946855044164835 1138.261556296296 L 11 1137 L 17.380887721185843 1150.5751343230784false3657215M1227 2475 C1321 2478 1343 2329 1344 2235 5false18trueM 25.946855044164835 1138.261556296296 L 11 1137 L 17.380887721185843 1150.5751343230784false3657216M1154 2030.5 L1154 2080.5 L1204 2030.5 z10true183657217M1344 390 C1345 427 1345 507 1344 560 5false18trueM 933.7463925514439 496.8704463525125 L 941 510 L 948.7437232747968 497.15341485672667false3657227M1344 2705 C1344 2769 1345 2815 1344 2913 5false183657228M1239 2807 C1283 2806 1345 2825 1344 2913 5false183657229M1440 2811 C1378 2812 1345 2851 1344 2913 5false183657230M1354 3512 C1354 3458 1344 3060 1344 2983 5false18trueM 25.946855044164835 1774.511556296296 L 11 1773.25 L 17.380887721185843 1786.8251343230784false3657231M1249 3217 C1316 3214 1343 3087 1344 2983 5false18trueM 25.946855044164835 1774.511556296296 L 11 1773.25 L 17.380887721185843 1786.8251343230784false3657232M1444 3217 C1383 3215 1345 3076 1344 2983 5false18trueM 25.946855044164835 1774.511556296296 L 11 1773.25 L 17.380887721185843 1786.8251343230784false3657233M1425 3046 C1396 3048 1342 3028 1344 2983 5false18trueM 25.946855044164835 1774.511556296296 L 11 1773.25 L 17.380887721185843 1786.8251343230784false3657234M1273 3049 C1325 3048 1342 3013 1344 2983 5false18trueM 25.946855044164835 1774.511556296296 L 11 1773.25 L 17.380887721185843 1786.8251343230784false3657235M1514 2418.5 L1514 2468.5 L1564 2418.5 z10true183657241M1454 3612 C1484 3612 1649 3610 1679 3610 5false183657242M1594 3529 C1594 3574 1610 3610 1679 3610 5false183657243M1579 3684 C1579 3635 1631 3610 1679 3610 5false183657244M2034 3613 C2004 3613 1859 3610 1829 3610 5false18trueM 572.1968550441649 2635.761556296296 L 557.25 2634.5 L 563.6308877211858 2648.075134323078false3657245M1909 3708 C1906 3644 1885 3610 1829 3610 5false18trueM 572.1968550441649 2635.761556296296 L 557.25 2634.5 L 563.6308877211858 2648.075134323078false3657254M2134 3513 C2134 3543 2131 2789 2131 2819 5false183657255M2233 2958 C2163 2960 2129 2894 2131 2819 5false183657256M2031 2883 C2062 2883 2131 2864 2131 2819 5false183657257M2029 2998 C2102 2997 2131 2905 2131 2819 5false183657258M2131 2570 C2131 2609 2132 2716 2131 2749 5false18trueM 1150.9468550441647 2548.261556296296 L 1136 2547 L 1142.380887721186 2560.575134323078false3657259M2021 2645 C2112 2647 2133 2690 2131 2749 5false18trueM 1150.9468550441647 2548.261556296296 L 1136 2547 L 1142.380887721186 2560.575134323078false3657260M2226 2645 C2166 2646 2131 2665 2131 2749 5false18trueM 1150.9468550441647 2548.261556296296 L 1136 2547 L 1142.380887721186 2560.575134323078false3657261M1856 3229 L1856 3279 L1906 3229 z10true183657262M2131 2370 C2131 2340 2128 2132 2128 2102 5false183657263M2020 2305 C2094 2302 2128 2186 2128 2102 5false183657264M2028 2155 C2076 2154 2126 2144 2128 2102 5false183657265M2228 2185 C2160 2187 2129 2169 2128 2102 5false183657266M2128 1825 C2128 1855 2128 2002 2128 2032 5false18trueM 1098.4468550441647 1802.011556296296 L 1083.5 1800.75 L 1089.880887721186 1814.3251343230784false3657267M2008 1905 C2091 1906 2128 1979 2128 2032 5false18trueM 1098.4468550441647 1802.011556296296 L 1083.5 1800.75 L 1089.880887721186 1814.3251343230784false3657268M2238 1910 C2183 1911 2127 1936 2128 2032 5false18trueM 1098.4468550441647 1802.011556296296 L 1083.5 1800.75 L 1089.880887721186 1814.3251343230784false3657269M1908 2347.5 L1908 2397.5 L1958 2347.5 z10true183657270M2128 1625 C2128 1595 2130 1382 2130 1352 5false183657271M2237 1580 C2162 1578 2130 1442 2130 1352 5false183657272M2030 1500 C2095 1498 2131 1457 2130 1352 5false183657273M2225 1435 C2175 1435 2130 1420 2130 1352 5false183657274M2130 1095 C2130 1125 2130 1252 2130 1282 5false18trueM 1297.1968550441647 1219.511556296296 L 1282.25 1218.25 L 1288.630887721186 1231.8251343230784false3657275M2025 1180 C2109 1179 2130 1212 2130 1282 5false18trueM 1297.1968550441647 1219.511556296296 L 1282.25 1218.25 L 1288.630887721186 1231.8251343230784false3657276M2230 1180 C2162 1180 2129 1201 2130 1282 5false18trueM 1297.1968550441647 1219.511556296296 L 1282.25 1218.25 L 1288.630887721186 1231.8251343230784false3657277M1905 1602.5 L1905 1652.5 L1955 1602.5 z10true183657296M2891 323 C2891 353 2893 775 2893 805 5false183657297M2765 548 C2827 548 2894 611 2893 805 5false183657298M2783 688 C2838 688 2896 731 2893 805 5false183657299M2988 683 C2940 682 2894 701 2893 805 5false183657300M2893 1053 C2893 1023 2893 905 2893 875 5false18trueM 1535.9468550441647 727.011556296296 L 1521 725.75 L 1527.380887721186 739.3251343230784false3657301M2768 993 C2809 993 2893 974 2893 875 5false18trueM 1535.9468550441647 727.011556296296 L 1521 725.75 L 1527.380887721186 739.3251343230784false3657302M2993 978 C2946 976 2892 960 2893 875 5false18trueM 1535.9468550441647 727.011556296296 L 1521 725.75 L 1527.380887721186 739.3251343230784false3657303M2658 1705.5 L2658 1755.5 L2708 1705.5 z10true183657304M2893 1253 C2893 1283 2895 1438 2895 1468 5false183657305M2792 1343 C2887 1342 2897 1391 2895 1468 5false183657306M2987 1398 C2950 1398 2897 1433 2895 1468 5false183657307M2985 1303 C2939 1305 2895 1382 2895 1468 5false183657308M2890 1748 C2890 1718 2895 1568 2895 1538 5false18trueM 1535.9468550441647 1680.761556296296 L 1521 1679.5 L 1527.380887721186 1693.0751343230784false3657309M2775 1658 C2819 1655 2895 1620 2895 1538 5false18trueM 1535.9468550441647 1680.761556296296 L 1521 1679.5 L 1527.380887721186 1693.0751343230784false3657310M2995 1628 C2951 1627 2895 1618 2895 1538 5false18trueM 1535.9468550441647 1680.761556296296 L 1521 1679.5 L 1527.380887721186 1693.0751343230784false3657311M2655 2448 L2655 2498 L2705 2448 z10true183657312M2890 1948 C2890 2058 2892 1984 2890 2077 5false183657313M2995 2257 C2930 2258 2892 2318 2890 2385 5false183657314M2779 2206 C2866 2210 2892 2281 2890 2385 5false183657315M2779 2304 C2770 2305 2890 2289 2890 2385 5false183657316M2890 2385 C2890 2320 2889 2242 2890 2147 5false18trueM 2274.6968550441647 2634.511556296296 L 2259.75 2633.25 L 2266.130887721186 2646.825134323078false3657317M3020 2725 C2971 2725 2890 2695 2890 2585 5false18trueM 2274.6968550441647 2634.511556296296 L 2259.75 2633.25 L 2266.130887721186 2646.825134323078false3657318M2789 2694 C2828 2692 2890 2649 2890 2585 5false18trueM 2274.6968550441647 2634.511556296296 L 2259.75 2633.25 L 2266.130887721186 2646.825134323078false3657319M3065 3072.5 L3065 3122.5 L3115 3072.5 z10true183657332M3601 3780 C3601 3750 3596 2912 3596 2882 5false183657333M3596 2530 C3596 2560 3596 2782 3596 2812 5false18trueM 2419.6968550441647 2343.261556296296 L 2404.75 2342 L 2411.130887721186 2355.575134323078false3657334M3596 2340 C3596 2310 3593 2070 3593 2040 5false183657335M3515 2125 C3583 2125 3593 2070 3593 2040 5false183657336M3498 2285 C3576 2285 3594 2145 3593 2040 5false183657337M3693 2170 C3646 2168 3594 2135 3593 2040 5false183657338M3593 1660 C3593 1690 3593 1940 3593 1970 5false18trueM 2419.6968550441647 1659.511556296296 L 2404.75 1658.25 L 2411.130887721186 1671.8251343230784false3657339M3493 1805 C3580 1805 3593 1914 3593 1970 5false18trueM 2419.6968550441647 1659.511556296296 L 2404.75 1658.25 L 2411.130887721186 1671.8251343230784false3657340M3698 1810 C3634 1810 3593 1863 3593 1970 5false18trueM 2419.6968550441647 1659.511556296296 L 2404.75 1658.25 L 2411.130887721186 1671.8251343230784false3657341M3358 2465 L3358 2515 L3408 2465 z10true183657342M3593 1470 C3593 1440 3591 1207 3591 1177 5false183657343M3489 1325 C3541 1322 3590 1282 3591 1177 5false183657344M3700 1305 C3646 1304 3591 1277 3591 1177 5false183657345M3594 860 C3594 890 3591 1077 3591 1107 5false18trueM 2304.6968550441647 1072.011556296296 L 2289.75 1070.75 L 2296.130887721186 1084.3251343230784false3657346M3479 960 C3549 960 3589 1011 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