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C-24 sterol reductase 3.0 1.0 1.0 P08524 UniProt C00448 KEGG Compound Lanosterin HMDB03896 HMDB CE(10:0) 1.0 P25087 UniProt HMDB00142 HMDB 559142 ChemSpider 440371 PubChem-compound HMDB01206 HMDB 90657655 PubChem-compound 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 1.0 CHEBI:16474 ChEBI P10614 UniProt 1.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 HMDB01217 HMDB BiologicalState210 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum Isopentenyl pyrophosphate 1.0 SMILES CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS 1.0 P41338 UniProt 23724571 PubChem-compound 57-87-4 CAS 7-Dehydrodesmosterol HMDB01423 HMDB HMDB03603 HMDB SMILES [H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C 979-92-0 CAS C00235 KEGG Compound CHEBI:16057 ChEBI C00009 KEGG Compound C00008 KEGG Compound 1158 ChemSpider C00007 KEGG Compound C00006 KEGG Compound 5a-cholesta-7,24-dien-3B-ol CHEBI:18009 ChEBI C5H12O7P2 Dimethylallylpyrophosphate 246.00583 Hydrogen Ion C00001 KEGG Compound NADP S-Adenosylhomocysteine 1.0 C00005 KEGG Compound 10477914 ChemSpider NADPH C00002 KEGG Compound P15496 UniProt 1.0 150-97-0 CAS HMDB01429 HMDB 1.0 Isopentenyl-diphosphate Delta-isomerase C37H64O2 CE(10:0) 540.49066 C00019 KEGG Compound C01107 KEGG Compound 1.0 Coenzyme A C00011 KEGG Compound C00010 KEGG Compound 1.0 P54839 UniProt C00013 KEGG Compound 2.7.1.36 false 2.7.1.36 Adenosine triphosphate + Mevalonic acid → Adenosine diphosphate + Mevalonic acid-5P LEFT_TO_RIGHT 2.7.4.2 false 2.7.4.2 Adenosine triphosphate + Mevalonic acid-5P → (S)-5-Diphosphomevalonic acid + Adenosine diphosphate LEFT_TO_RIGHT 4.1.1.33 false 4.1.1.33 (S)-5-Diphosphomevalonic acid + Adenosine triphosphate → Adenosine diphosphate + Carbon dioxide + Isopentenyl pyrophosphate + Phosphate LEFT_TO_RIGHT 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc 1183-04-6 CAS 2.3.3.10 false 2.3.3.10 Acetoacetyl-CoA + Acetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A LEFT_TO_RIGHT C6H14O10P2 (S)-5-Diphosphomevalonic acid 308.00623 H Hydrogen Ion 1.007825 CHEBI:1949 ChEBI 56-65-5 CAS 443212 PubChem-compound C00021 KEGG Compound 11090531 PubChem-compound 389510 ChemSpider 388662 ChemSpider C00024 KEGG Compound 1264-57-9 CAS 1.0 CHEBI:28493 ChEBI (S)-5-Diphosphomevalonic acid NADP CL:0000000 CELL TYPE ONTOLOGY 1.0 SMILES CC(C)=CCC\C(C)=C/CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C Formic acid C-24 sterol reductase SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 1.0 1.0 GERANYL-PP BioCyc Squalene Methylsterol monooxygenase 3-Keto-4-methylzymosterol SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O 10148626 ChemSpider 1.3.1.70 false 1.3.1.70 4,4-Dimethylcholesta-8,14,24-trienol + NADPH → 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP LEFT_TO_RIGHT SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O 4α-formyl-5α-cholesta-8,24-dien-3β-ol 3-Hydroxy-3-methylglutaryl-CoA HMDB00538 HMDB Reaction6891 false Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate LEFT_TO_RIGHT Reaction6892 false Geranyl-PP + Isopentenyl pyrophosphate → Farnesyl pyrophosphate + Pyrophosphate LEFT_TO_RIGHT 2.5.1.21 false 2.5.1.21 2 Farnesyl pyrophosphate + NADPH → NADP + 2 Pyrophosphate + Squalene LEFT_TO_RIGHT 1.14.13.132 false 1.14.13.132 NADPH + Oxygen + Squalene → (S)-2,3-Epoxysqualene + NADP + Water LEFT_TO_RIGHT 5.4.99.7 false 5.4.99.7 (S)-2,3-Epoxysqualene → Lanosterin LEFT_TO_RIGHT HMDB02719 HMDB C15777 KEGG Compound 1.14.13.70 false 1.14.13.70 Lanosterin + 3 NADPH + 3 Oxygen → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + 3 NADP + 4 Water LEFT_TO_RIGHT 7448-02-4 CAS C01143 KEGG Compound 2.0 C00058 KEGG Compound 436 ChemSpider (S)-2,3-Epoxysqualene 9029-62-3 CAS SMILES CC(O)(CCO)CC(O)=O FORMATE BioCyc 46173808 PubChem-compound CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 FARNESYL-PP BioCyc Lanosterol 14-alpha demethylase C27H42O 7-Dehydrodesmosterol 382.32358 1.0 ergosta-5,7,22,24(28)-tetraen-3-β-ol 962 PubChem-compound 31983 ChemSpider 1.0 CO2 Carbon dioxide 43.98983 Coenzyme A C00080 KEGG Compound SMILES O=O SMILES C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 2.0 14265-44-2 CAS Diphosphomevalonate decarboxylase 21865764 ChemSpider (S)-2,3-Epoxysqualene 644102 PubChem-compound Acetyl-CoA 1.0 SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 64-18-6 CAS 1.0 1.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase ReactionCatalysis7248 ACTIVATION 29908-03-0 CAS 2.0 Farnesyl pyrophosphate ReactionCatalysis7250 ACTIVATION Dimethylallylpyrophosphate HMDB00961 HMDB 977 PubChem-compound ReactionCatalysis7251 ACTIVATION 2.0 627 ChemSpider 1.0 1.0 5a-cholesta-7,24-dien-3B-ol 1.0 17215925 ChemSpider P38604 UniProt 1.0 1.0 Acetoacetyl-CoA 3.0 1.0 Lanosterol synthase Cholesterol Methylsterol monooxygenase 1.0 ReactionCatalysis6900 ACTIVATION 6816 PubChem-compound C27H46O Cholesterol 386.35486 1.0 C05107 KEGG Compound 1.0 C05108 KEGG Compound C05103 KEGG Compound Farnesyl pyrophosphate synthase 79-63-0 CAS 278 ChemSpider C-22 sterol desaturase C-5 sterol desaturase 274 ChemSpider C-24 sterol reductase 3-keto sterol reductase C-8 sterol isomerase Sterol 24-C-methyltransferase CPD-641 BioCyc Pyrophosphate O4P Phosphate 94.95342 1.0 C-3 sterol dehydrogenase Lanosterin 25994967 ChemSpider Hydrogen Ion 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 90659175 PubChem-compound Episterol NADPH BioCyc 50990081 PubChem-compound Carbon dioxide CPD-6641 BioCyc 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol SMILES [O-]P([O-])([O-])=O 1.0 mevalonate kinase 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 3434726 ChemSpider 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 3.0 ferricytochrome c NADPH 1.0 Geranyl-PP 474-68-0 CAS 4.0 Geranyl-PP Lanosterol synthase squalene monooxygenase 1.0 Delta(14)-sterol reductase Lanosterol 14-alpha demethylase Isopentenyl-diphosphate Delta-isomerase Diphosphomevalonate decarboxylase SMILES O=C=O 1.0 Squalene synthase Farnesyl pyrophosphate synthase Phosphomevalonate kinase C25H40N7O18P3S Acetoacetyl-CoA 851.13635 1.0 5957 PubChem-compound P53199 UniProt Reaction989 false 7-Dehydrodesmosterol → Desmosterol LEFT_TO_RIGHT CHEBI:15991 ChEBI C-22 sterol desaturase 1.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 HMDB01090 HMDB 11025495 PubChem-compound P12684 UniProt P12683 UniProt C01802 KEGG Compound 4,4-Dimethylcholesta-8,14,24-trienol SMILES CCCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C ferrocytochrome c C-22 sterol desaturase 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol P32462 UniProt 1.0 14000-31-8 CAS P07277 UniProt CO-A BioCyc LANOSTEROL BioCyc 5,7,24(28)-Ergostatrienol 5675 ChemSpider 72-89-9 CAS 1.0 1.0 1.0 216175 ChemSpider SMILES C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O Water 1.0 Cell 1.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 Phosphomevalonate kinase 6557 ChemSpider 1.0 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol HMDB01285 HMDB CHEBI:50586 ChEBI 1.0 HMDB01286 HMDB CHEBI:25351 ChEBI CH2O2 Formic acid 46.005478 BiologicalState160 Saccharomyces cerevisiae, Cell, Cytosol 439577 PubChem-compound GO:0005783 GENE ONTOLOGY Water Squalene synthase 1.0 CHEBI:17737 ChEBI 1.0 P32476 UniProt Formic acid 440558 PubChem-compound 7782-44-7 CAS 1.0 Lanosterol 14-alpha demethylase C-8 sterol isomerase 21775588 PubChem-compound 358-71-4 CAS 392413 ChemSpider 1.0 1.0 C00751 KEGG Compound HMDB01023 HMDB HMDB02111 HMDB CHEBI:30751 ChEBI Reaction6902 false 3-Keto-4-methylzymosterol + NADPH → 4a-Methylzymosterol + NADP LEFT_TO_RIGHT 3-Hydroxy-3-methylglutaryl-CoA 4225619 PubChem-compound CHEBI:15377 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] Acetoacetyl-CoA C5H12 ferrocytochrome c 72.0939 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O C42H68O13 ferricytochrome c 780.466 1.0 SMILES [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)CCC=C(C)C Oxygen 9200676 ChemSpider Cholesterol-esters BioCyc Squalene acetyl-CoA C-acetyltransferase 30776536 ChemSpider CHEBI:15345 ChEBI 1195 PubChem-compound 1.3.1.71 false 1.3.1.71 ergosta-5,7,22,24(28)-tetraen-3-β-ol + Hydrogen Ion + NADPH → Ergosterol + NADP LEFT_TO_RIGHT 1.0 1.0 HMDB01484 HMDB Reaction6920 false 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + Hydrogen Ion + NADPH + Oxygen → 4α-formyl-5α-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT Reaction6921 false 4α-formyl-5α-cholesta-8,24-dien-3β-ol + NADPH + Oxygen → 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT Reaction6922 false 4α-carboxy-5α-cholesta-8,24-dien-3β-ol + NADP → 5α-cholesta-8,24-dien-3-one + Carbon dioxide + NADPH LEFT_TO_RIGHT 1.0 Reaction6923 false 5α-cholesta-8,24-dien-3-one + Hydrogen Ion + NADPH → NADP + Zymosterol LEFT_TO_RIGHT 2.1.1.41 false 2.1.1.41 S-Adenosylmethionine + Zymosterol → Hydrogen Ion + S-Adenosylhomocysteine + fecosterol LEFT_TO_RIGHT 5.-.-.- false 5.-.-.- fecosterol → Episterol LEFT_TO_RIGHT 1.14.19.20 false 1.14.19.20 Episterol + Hydrogen Ion + Oxygen + ferrocytochrome c → 5,7,24(28)-Ergostatrienol + Water + ferricytochrome c LEFT_TO_RIGHT 20036827 ChemSpider 1.14.19.41 false 1.14.19.41 5,7,24(28)-Ergostatrienol + Hydrogen Ion + NADPH + Oxygen → ergosta-5,7,22,24(28)-tetraen-3-β-ol + NADP + Water LEFT_TO_RIGHT (S)-5-Diphosphomevalonic acid CHEBI:1307929 ChEBI 1.0 Carbon dioxide 1.1.1.170 false 1.1.1.170 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol + NADP → 3-Keto-4-methylzymosterol + Carbon dioxide + NADPH LEFT_TO_RIGHT 64284-64-6 CAS Reaction6919 false 4a-Methylzymosterol + Hydrogen Ion + NADPH + Oxygen → 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT CHEBI:16680 ChEBI SMILES CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CHEBI:15351 ChEBI HMDB01251 HMDB 1.1.1.34 false 1.1.1.34 3-Hydroxy-3-methylglutaryl-CoA + NADPH → Coenzyme A + Mevalonic acid + NADP LEFT_TO_RIGHT Reaction6914 false 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + Hydrogen Ion + NADPH + Oxygen → 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT Reaction6915 false 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + Hydrogen Ion + NADPH + Oxygen → 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT Reaction6916 false 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NADPH + Oxygen → 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol + NADP + Water LEFT_TO_RIGHT 85-61-0 CAS 313-04-2 CAS 4a-Methylzymosterol C28H46O 4a-Methylzymosterol 398.35486 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 HMDB01343 HMDB 1.0 HMDB00256 HMDB 388357 ChemSpider 6022 PubChem-compound 3.0 C28H44O Ergosterol 396.3392 HMDB01347 HMDB 1.0 C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc HMDB00250 HMDB 388353 ChemSpider HMDB01341 HMDB CHOLESTEROL BioCyc 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 389458 ChemSpider 4a-Methylzymosterol 111-02-4 CAS ATP BioCyc 1.0 C15816 KEGG Compound Mevalonic acid P54781 UniProt C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 Sterol 24-C-methyltransferase C15H23N6O5S S-Adenosylmethionine 399.14505 1.0 2.0 1.0 C00332 KEGG Compound 952 ChemSpider 1.0 HMDB59597 HMDB Ergosterol fecosterol EPOXYSQUALENE BioCyc 1.0 1.0 Acetyl-CoA C00341 KEGG Compound CHEBI:17211 ChEBI 445713 PubChem-compound 1010 ChemSpider PPI BioCyc ReactionCatalysis6485 ACTIVATION 1.0 1.0 ReactionCatalysis6891 ACTIVATION 1.0 HMDB00217 HMDB SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 Cytosol C00356 KEGG Compound 1.0 SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C/CC\C=C(/C)CC\C=C(\C)CC[C@]1([H])OC1(C)C C02530 KEGG Compound C14H20N6O5S S-Adenosylhomocysteine 384.12158 1.0 C10H20O7P2 Geranyl-PP 314.06842 ReactionCatalysis6895 ACTIVATION 2.0 ReactionCatalysis6894 ACTIVATION ReactionCatalysis6893 ACTIVATION ReactionCatalysis6892 ACTIVATION ReactionCatalysis6899 ACTIVATION ReactionCatalysis6898 ACTIVATION ReactionCatalysis6897 ACTIVATION ReactionCatalysis6896 ACTIVATION HMDB00221 HMDB C00129 KEGG Compound 1.0 HMDB00227 HMDB C29H48O 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 412.3705 C01694 KEGG Compound ERGOSTEROL BioCyc CHEBI:18361 ChEBI CHEBI:18367 ChEBI 1032 ChemSpider CHEBI:18364 ChEBI Delta(14)-sterol reductase C-3 sterol dehydrogenase Oxygen 57-88-5 CAS Methylsterol monooxygenase 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol Hydroxymethylglutaryl-CoA synthase C30H50O Lanosterin 426.38617 763-10-0 CAS 388531 ChemSpider Zymosterol NAD(P) BioCyc squalene monooxygenase Pyrophosphate 388301 ChemSpider http://identifiers.org/smpdb/SMP02436 SMPDB 3.0 Lanosterol synthase 445995 PubChem-compound Isopentenyl-diphosphate Delta-isomerase 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc 3-keto sterol reductase fecosterol CPD-499 BioCyc 647 PubChem-compound 388517 ChemSpider acetyl-CoA C-acetyltransferase 372-97-4 CAS 1.0 C28H46O Episterol 398.35486 SMILES CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 22298941 PubChem-compound 22298942 PubChem-compound Decanoyl-CoA (n-C10:0CoA) C31H54N7O17P3S Decanoyl-CoA (n-C10:0CoA) 921.251 C-3 sterol dehydrogenase 22298940 PubChem-compound C15H28O7P2 Farnesyl pyrophosphate 382.131 53477723 PubChem-compound 1.0 7732-18-5 CAS 44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET BioCyc 1.0 Farnesyl pyrophosphate synthase 1.0 2.3.1.9 false 2.3.1.9 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE 5a-cholesta-7,24-dien-3B-ol 1.0 SMILES CCCCC CPD-4578 BioCyc C00187 KEGG Compound SMILES CC(CC\C=C(/C)COC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C1CCC2(C)C3CC=C4C(CCC(O)C4(C)C)C3(C)C(=O)CC12C S-Adenosylhomocysteine 2.0 SMILES [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C C28H44O 3-Keto-4-methylzymosterol 396.3392 HMDB00878 HMDB 1.0 HMDB01967 HMDB 1.0 7448-03-5 CAS 5800 ChemSpider 53477900 PubChem-compound Cholesterol CHEBI:27910 ChEBI squalene monooxygenase Squalene synthase 4α-carboxy-5α-cholesta-8,24-dien-3β-ol C29H46O2 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 426.3498 C29H45O3 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol 441.33743 SMILES OC=O C29H48O2 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 428.36542 C28H43O3 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 427.32178 C27H42O 5α-cholesta-8,24-dien-3-one 382.32358 C28H46O2 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 414.3498 C28H44O2 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.33414 58-64-0 CAS 1.0 C01054 KEGG Compound 1.0 4α-formyl-5α-cholesta-8,24-dien-3β-ol C27H44O Desmosterol 384.3392 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol C28H46O fecosterol 398.35486 C28H44O 5,7,24(28)-Ergostatrienol 396.3392 C27H44O Zymosterol 384.3392 acetyl-CoA C-acetyltransferase C28H42O ergosta-5,7,22,24(28)-tetraen-3-β-ol 394.32358 1.0 444493 PubChem-compound 4932 TAXONOMY 1.0 22833512 PubChem-compound 25246222 PubChem-compound C-8 sterol isomerase Hydroxymethylglutaryl-CoA synthase ACETYL-COA BioCyc Mevalonic acid-5P H2O Water 18.010565 22212495 PubChem-compound 3-keto sterol reductase 1.0 1.0 P25340 UniProt 1.0 1.0 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol P29704 UniProt CHEBI:16933 ChEBI ferricytochrome c 1.0 CPD-4141 BioCyc 1.0 SMILES O Acetyl-CoA C6H12O4 Mevalonic acid 148.07356 CHEBI:16928 ChEBI C-5 sterol desaturase SQUALENE BioCyc Farnesyl pyrophosphate synthase 3425 PubChem-compound 1.0 1.0 92746 PubChem-compound 1.0 393270 ChemSpider 5,7,24(28)-Ergostatrienol ergosta-5,7,22,24(28)-tetraen-3-β-ol ADP BioCyc Sterol 24-C-methyltransferase 90659076 PubChem-compound HMDB00939 HMDB Dimethylallylpyrophosphate 1553-55-5 CAS 53-59-8 CAS Reaction7263 false Isopentenyl pyrophosphate → Dimethylallylpyrophosphate LEFT_TO_RIGHT 358-72-5 CAS SMILES [H][C@@](C)(CCC(=C)C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12C Ergosterol 1038 PubChem-compound 3-Keto-4-methylzymosterol GO:0005829 GENE ONTOLOGY CHEBI:505093 ChEBI ADENOSYL-HOMO-CYS BioCyc 1.0 SMILES CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N Desmosterol Phosphomevalonate kinase C21H30N7O17P3 NADPH 745.0911 mevalonate kinase C21H29N7O17P3 NADP 744.08325 449 PubChem-compound mevalonate kinase C5H12O7P2 Isopentenyl pyrophosphate 246.00583 Mevalonic acid-5P 5α-cholesta-8,24-dien-3-one P24521 UniProt 124-38-9 CAS Mevalonic acid 1.0 CHEBI:15414 ChEBI P32377 UniProt CHEBI:15899 ChEBI 440615 PubChem-compound Farnesyl pyrophosphate synthase SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Adenosine triphosphate Acetoacetyl-CoA SMILES NC(=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=C(N)N=CN=C23)[C@H](O)[C@@H]1O Reaction7265 false Zymosterol ↔ 5a-cholesta-7,24-dien-3B-ol REVERSIBLE Reaction7267 false Desmosterol → Cholesterol LEFT_TO_RIGHT Reaction7266 false 5a-cholesta-7,24-dien-3B-ol → 7-Dehydrodesmosterol LEFT_TO_RIGHT Reaction7269 false Cholesterol + Decanoyl-CoA (n-C10:0CoA) ↔ CE(10:0) + Coenzyme A REVERSIBLE 393471 ChemSpider 53-57-6 CAS 1.0 S-ADENOSYLMETHIONINE BioCyc C05274 KEGG Compound O7P2 Pyrophosphate 173.91193 4-METHYL-824-CHOLESTADIENOL BioCyc 439418 PubChem-compound C30H50 Squalene 410.39127 CHEBI:17813 ChEBI 439400 PubChem-compound Adenosine triphosphate Farnesyl pyrophosphate C10H15N5O10P2 Adenosine diphosphate 427.02942 C6H13O7P Mevalonic acid-5P 228.03989 SMILES [H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C P53045 UniProt Endoplasmic Reticulum 1.0 CPD-8587 BioCyc HMDB01185 HMDB HMDB01188 HMDB CHEBI:15441 ChEBI Adenosine diphosphate 4.0 CHEBI:15440 ChEBI SMILES [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)C CHEBI:1146900 ChEBI ReactionCatalysis6858 ACTIVATION ReactionCatalysis6857 ACTIVATION ReactionCatalysis6856 ACTIVATION 1.0 Hydroxymethylglutaryl-CoA synthase ReactionCatalysis6855 ACTIVATION HMDB06404 HMDB S-Adenosylmethionine Coenzyme A ReactionCatalysis6869 ACTIVATION ReactionCatalysis6868 ACTIVATION C21H36N7O16P3S Coenzyme A 767.11523 Adenosine diphosphate S-Adenosylmethionine ReactionCatalysis6862 ACTIVATION 18971002 PubChem-compound ReactionCatalysis6860 ACTIVATION ReactionCatalysis6866 ACTIVATION ReactionCatalysis6865 ACTIVATION ReactionCatalysis6864 ACTIVATION ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI acetyl-CoA C-acetyltransferase SMILES CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C SMILES CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 1.0 SMILES [H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C 1.0 C27H44N7O20P3S 3-Hydroxy-3-methylglutaryl-CoA 911.1575 O2 Oxygen 31.98983 439214 PubChem-compound 1.0 SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C=O)[C@]1([H])CC3 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol ReactionCatalysis6873 ACTIVATION SMILES C[C@H](CCC=C(C)C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(CO)[C@@H]1CC3 SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(CO)[C@]1([H])CC3 SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)C(C)(C([O-])=O)[C@]1([H])CC3 Isopentenyl pyrophosphate 439218 PubChem-compound CHEBI:16521 ChEBI Q12452 UniProt 391478 ChemSpider SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C([O-])=O)[C@]1([H])CC3 P32353 UniProt SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C=O)[C@]1([H])CC3 CHEBI:16526 ChEBI SMILES [H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C[C@]1([H])CC3)[C@H](C)CCC=C(C)C 73566-35-5 CAS CHEBI:16761 ChEBI 246983 PubChem-compound ReactionCatalysis6889 ACTIVATION 90658366 PubChem-compound Episterol ferrocytochrome c 4,4-Dimethylcholesta-8,14,24-trienol ReactionCatalysis6882 ACTIVATION 1.0 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol P32352 UniProt ReactionCatalysis6888 ACTIVATION SMILES [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)CCC(=C)C(C)C ReactionCatalysis6887 ACTIVATION SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3 ReactionCatalysis6886 ACTIVATION SMILES CC(C)C(=C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C SMILES CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C C01724 KEGG Compound 1.0 Cholesterol biosynthesis and metabolism CE(10:0) HMDB06838 HMDB 1715-86-2 CAS 1.0 SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O 1420-36-6 CAS 2.0 HMDB00067 HMDB CHEBI:17436 ChEBI Zymosterol HMDB06847 HMDB 3-hydroxy-3-methylglutaryl-coenzyme A reductase 5886 PubChem-compound 1.0 CHEBI:16584 ChEBI Phosphate SMILES C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3 280 PubChem-compound C-5 sterol desaturase 5α-cholesta-8,24-dien-3-one Phosphate PW002545 PathWhiz CHEBI:15467 ChEBI CHEBI:17407 ChEBI C00418 KEGG Compound HMDB01120 HMDB SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O Diphosphomevalonate decarboxylase 1.0 Delta(14)-sterol reductase SMILES [H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C SMILES CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O 3.0 1.0 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol HMDB01377 HMDB 1061 PubChem-compound HMDB01375 HMDB 24762165 PubChem-compound 11975273 PubChem-compound