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C-24 sterol reductase C28H46O 4a-Methylzymosterol 398.35486 HMDB01343 HMDB 3.0 HMDB00256 HMDB 388357 ChemSpider C28H44O Ergosterol 396.3392 6022 PubChem-compound 1.0 HMDB01347 HMDB C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc HMDB00250 HMDB 388353 ChemSpider HMDB01341 HMDB C45H80O2 CE(18:0) 652.61584 CHOLESTEROL BioCyc http://identifiers.org/smpdb/SMP02441 SMPDB 389458 ChemSpider P08524 UniProt C00448 KEGG Compound HMDB03896 HMDB 4a-Methylzymosterol 111-02-4 CAS NADPH ATP BioCyc P25087 UniProt HMDB00142 HMDB C15816 KEGG Compound 1.0 559142 ChemSpider 440371 PubChem-compound Mevalonic acid P54781 UniProt C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 Sterol 24-C-methyltransferase C15H23N6O5S S-Adenosylmethionine 399.14505 HMDB01206 HMDB 90657655 PubChem-compound 1.0 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 1.0 C00332 KEGG Compound CHEBI:16474 ChEBI P10614 UniProt 952 ChemSpider HMDB59597 HMDB Ergosterol fecosterol EPOXYSQUALENE BioCyc HMDB01217 HMDB 1.0 BiologicalState210 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum C00341 KEGG Compound BiologicalState213 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum Membrane Isopentenyl pyrophosphate CHEBI:17211 ChEBI Cholesterol 445713 PubChem-compound 1010 ChemSpider 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 PPI BioCyc P41338 UniProt ReactionCatalysis6485 ACTIVATION 1.0 57-87-4 CAS 23724571 PubChem-compound HMDB01423 HMDB ReactionCatalysis6891 ACTIVATION ReactionCatalysis6890 ACTIVATION HMDB00217 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 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 979-92-0 CAS C00356 KEGG Compound C00235 KEGG Compound 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 CHEBI:16057 ChEBI C02530 KEGG Compound C14H20N6O5S S-Adenosylhomocysteine 384.12158 1.0 C10H20O7P2 Geranyl-PP 314.06842 ReactionCatalysis6895 ACTIVATION ReactionCatalysis6894 ACTIVATION ReactionCatalysis6893 ACTIVATION ReactionCatalysis6892 ACTIVATION ReactionCatalysis6899 ACTIVATION ReactionCatalysis6898 ACTIVATION ReactionCatalysis6897 ACTIVATION ReactionCatalysis6896 ACTIVATION HMDB00221 HMDB C00009 KEGG Compound C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider 1.0 C00007 KEGG Compound C00006 KEGG Compound 5a-cholesta-7,24-dien-3B-ol HMDB00227 HMDB CHEBI:18009 ChEBI C5H12O7P2 Dimethylallylpyrophosphate 246.00583 C29H48O 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 412.3705 C00001 KEGG Compound C01694 KEGG Compound ERGOSTEROL BioCyc NADP S-Adenosylhomocysteine CHEBI:18361 ChEBI 1.0 C00005 KEGG Compound 10477914 ChemSpider CHEBI:18367 ChEBI 1032 ChemSpider CHEBI:18364 ChEBI C00002 KEGG Compound P15496 UniProt 150-97-0 CAS HMDB01429 HMDB C-3 sterol dehydrogenase 1.0 Oxygen 57-88-5 CAS Isopentenyl-diphosphate Delta-isomerase Methylsterol monooxygenase 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol Hydroxymethylglutaryl-CoA synthase C00019 KEGG Compound C01107 KEGG Compound C30H50O Lanosterin 426.38617 1.0 763-10-0 CAS C00011 KEGG Compound C00010 KEGG Compound P54839 UniProt 388531 ChemSpider C00013 KEGG Compound Zymosterol 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 NAD(P) BioCyc 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc HMDB10368 HMDB 2.3.3.10 false 2.3.3.10 Acetoacetyl-CoA + Acetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A LEFT_TO_RIGHT Pyrophosphate H Hydrogen Ion 1.007825 C6H14O10P2 (S)-5-Diphosphomevalonic acid 308.00623 388301 ChemSpider CHEBI:1949 ChEBI 3.0 Lanosterol synthase Coenzyme A 445995 PubChem-compound 11090531 PubChem-compound 56-65-5 CAS 443212 PubChem-compound C00021 KEGG Compound 388662 ChemSpider C00024 KEGG Compound acetyl-CoA C-acetyltransferase 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc 3-keto sterol reductase 1.0 CPD-499 BioCyc 647 PubChem-compound 388517 ChemSpider CL:0000000 CELL TYPE ONTOLOGY 372-97-4 CAS 1.0 1.0 3-Hydroxy-3-methylglutaryl-CoA C28H46O Episterol 398.35486 SMILES CC(C)=CCC\C(C)=C/CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C 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 1.0 1.0 SMILES [O-]P([O-])(=O)OP([O-])([O-])=O GERANYL-PP BioCyc Squalene 22298941 PubChem-compound 22298942 PubChem-compound 3-Keto-4-methylzymosterol Desmosterol 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 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 C-3 sterol dehydrogenase 1.14.13.132 false 1.14.13.132 NADPH + Oxygen + Squalene → (S)-2,3-Epoxysqualene + NADP + Water LEFT_TO_RIGHT HMDB02719 HMDB 5.4.99.7 false 5.4.99.7 (S)-2,3-Epoxysqualene → Lanosterin LEFT_TO_RIGHT 22298940 PubChem-compound 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 C15H28O7P2 Farnesyl pyrophosphate 382.131 53477723 PubChem-compound 7448-02-4 CAS C01143 KEGG Compound 7732-18-5 CAS C00058 KEGG Compound 436 ChemSpider 9029-62-3 CAS SMILES CC(O)(CCO)CC(O)=O 44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET BioCyc 1.0 FORMATE BioCyc 46173808 PubChem-compound 2.3.1.9 false 2.3.1.9 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 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 FARNESYL-PP BioCyc C27H42O 7-Dehydrodesmosterol 382.32358 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 HMDB01967 HMDB 962 PubChem-compound 31983 ChemSpider 7448-03-5 CAS 1.0 5800 ChemSpider 53477900 PubChem-compound 3-hydroxy-3-methylglutaryl-coenzyme A reductase CO2 Carbon dioxide 43.98983 Coenzyme A C00080 KEGG Compound SMILES O=O 1.0 CHEBI:27910 ChEBI squalene monooxygenase Squalene synthase 4α-carboxy-5α-cholesta-8,24-dien-3β-ol 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 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 14265-44-2 CAS C28H44O2 4α-formyl-5α-cholesta-8,24-dien-3β-ol 412.33414 58-64-0 CAS 1.0 C01054 KEGG Compound 21865764 ChemSpider 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 Reaction7302 false Cholesterol + Stearidonoyl CoA → CE(18:0) + Coenzyme A LEFT_TO_RIGHT acetyl-CoA C-acetyltransferase C28H42O ergosta-5,7,22,24(28)-tetraen-3-β-ol 394.32358 1.0 (S)-2,3-Epoxysqualene 644102 PubChem-compound 4932 TAXONOMY 444493 PubChem-compound Mevalonic acid Acetyl-CoA 1.0 SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 64-18-6 CAS 1.0 22833512 PubChem-compound 25246222 PubChem-compound C-8 sterol isomerase ACETYL-COA BioCyc Mevalonic acid-5P H2O Water 18.010565 22212495 PubChem-compound Acetyl-CoA ReactionCatalysis7248 ACTIVATION 29908-03-0 CAS ReactionCatalysis7250 ACTIVATION 1.0 HMDB00961 HMDB 977 PubChem-compound ReactionCatalysis7251 ACTIVATION 2.0 627 ChemSpider P25340 UniProt 1.0 1.0 24769460 ChemSpider 1.0 5a-cholesta-7,24-dien-3B-ol P29704 UniProt 17215925 ChemSpider 7-Dehydrodesmosterol Acetoacetyl-CoA P38604 UniProt CHEBI:16933 ChEBI ferricytochrome c 1.0 CPD-4141 BioCyc SMILES O 3.0 C6H12O4 Mevalonic acid 148.07356 CHEBI:16928 ChEBI 1.0 C-5 sterol desaturase SQUALENE BioCyc 3425 PubChem-compound 1.0 92746 PubChem-compound Methylsterol monooxygenase 1.0 ReactionCatalysis6900 ACTIVATION 393270 ChemSpider 6816 PubChem-compound ergosta-5,7,22,24(28)-tetraen-3-β-ol C27H46O Cholesterol 386.35486 ADP BioCyc 52922033 PubChem-compound 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 C05107 KEGG Compound 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 C39H62N7O17P3S Stearidonoyl CoA 1025.3136 1.0 1038 PubChem-compound C05108 KEGG Compound Farnesyl pyrophosphate synthase C05103 KEGG Compound 79-63-0 CAS 278 ChemSpider C-22 sterol desaturase C-5 sterol desaturase C-24 sterol reductase 274 ChemSpider 3-keto sterol reductase C-8 sterol isomerase Sterol 24-C-methyltransferase CHEBI:505093 ChEBI ADENOSYL-HOMO-CYS BioCyc 1.0 CPD-641 BioCyc O4P Phosphate 94.95342 Lanosterin 25994967 ChemSpider C21H30N7O17P3 NADPH 745.0911 Hydrogen Ion mevalonate kinase C21H29N7O17P3 NADP 744.08325 90659175 PubChem-compound 1.0 Episterol NADPH BioCyc 449 PubChem-compound 50990081 PubChem-compound C5H12O7P2 Isopentenyl pyrophosphate 246.00583 CPD-6641 BioCyc SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N CE(18:0) SMILES [O-]P([O-])([O-])=O 5α-cholesta-8,24-dien-3-one P24521 UniProt 124-38-9 CAS 1.0 mevalonate kinase 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 CHEBI:15414 ChEBI 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 P32377 UniProt CHEBI:15899 ChEBI Stearidonoyl CoA Farnesyl pyrophosphate synthase NADPH 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 1.0 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 474-68-0 CAS 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 393471 ChemSpider 53-57-6 CAS Geranyl-PP Lanosterol synthase 1.0 squalene monooxygenase Delta(14)-sterol reductase Lanosterol 14-alpha demethylase C16163 KEGG Compound Isopentenyl-diphosphate Delta-isomerase Diphosphomevalonate decarboxylase SMILES O=C=O 1.0 S-ADENOSYLMETHIONINE BioCyc Squalene synthase Farnesyl pyrophosphate synthase Phosphomevalonate kinase O7P2 Pyrophosphate 173.91193 C25H40N7O18P3S Acetoacetyl-CoA 851.13635 4-METHYL-824-CHOLESTADIENOL BioCyc 5957 PubChem-compound 439418 PubChem-compound C30H50 Squalene 410.39127 1.0 P53199 UniProt CHEBI:17813 ChEBI Reaction989 false 7-Dehydrodesmosterol → Desmosterol LEFT_TO_RIGHT 1.0 CHEBI:15991 ChEBI 439400 PubChem-compound Farnesyl pyrophosphate C10H15N5O10P2 Adenosine diphosphate 427.02942 HMDB01090 HMDB 11025495 PubChem-compound C6H13O7P Mevalonic acid-5P 228.03989 P12684 UniProt P12683 UniProt 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 C01802 KEGG Compound P53045 UniProt 4,4-Dimethylcholesta-8,14,24-trienol HMDB06519 HMDB Endoplasmic Reticulum Endoplasmic Reticulum Membrane CPD-8587 BioCyc HMDB01185 HMDB Adenosine diphosphate HMDB01188 HMDB CHEBI:15441 ChEBI 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 ferrocytochrome c C-22 sterol desaturase CHEBI:1146900 ChEBI ReactionCatalysis6858 ACTIVATION ReactionCatalysis6857 ACTIVATION ReactionCatalysis6856 ACTIVATION 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol Hydroxymethylglutaryl-CoA synthase P32462 UniProt ReactionCatalysis6855 ACTIVATION 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 ReactionCatalysis6869 ACTIVATION ReactionCatalysis6868 ACTIVATION C21H36N7O16P3S Coenzyme A 767.11523 Water S-Adenosylmethionine 1.0 ReactionCatalysis6862 ACTIVATION 18971002 PubChem-compound ReactionCatalysis6860 ACTIVATION ReactionCatalysis6866 ACTIVATION ReactionCatalysis6865 ACTIVATION ReactionCatalysis6864 ACTIVATION Cell ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI Phosphomevalonate kinase 6557 ChemSpider 2.0 53480457 PubChem-compound 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 1.0 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol HMDB01285 HMDB 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 CHEBI:50586 ChEBI 1.0 HMDB01286 HMDB C27H44N7O20P3S 3-Hydroxy-3-methylglutaryl-CoA 911.1575 CHEBI:25351 ChEBI O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 439214 PubChem-compound 439577 PubChem-compound SMILES CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C GO:0005789 GENE ONTOLOGY 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 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 GO:0005783 GENE ONTOLOGY 439218 PubChem-compound CHEBI:16521 ChEBI Q12452 UniProt 1.0 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 CHEBI:17737 ChEBI 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 P32476 UniProt 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 Formic acid 440558 PubChem-compound 73566-35-5 CAS CHEBI:16761 ChEBI 7782-44-7 CAS 246983 PubChem-compound ReactionCatalysis6889 ACTIVATION 90658366 PubChem-compound Lanosterol 14-alpha demethylase ReactionCatalysis6882 ACTIVATION P32352 UniProt 21775588 PubChem-compound 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 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 ReactionCatalysis6886 ACTIVATION 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 1.0 358-71-4 CAS HMDB06838 HMDB 392413 ChemSpider 1.0 1715-86-2 CAS C00751 KEGG Compound HMDB01023 HMDB HMDB02111 HMDB SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O CHEBI:30751 ChEBI 3-Hydroxy-3-methylglutaryl-CoA 1420-36-6 CAS 2.0 CHEBI:15377 ChEBI HMDB00067 HMDB CHEBI:17436 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] Acetoacetyl-CoA PW002551 PathWhiz HMDB06847 HMDB 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 5886 PubChem-compound 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 CHEBI:16584 ChEBI SMILES C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3 9200676 ChemSpider Cholesterol-esters BioCyc 280 PubChem-compound 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 Phosphate CHEBI:15467 ChEBI 30776536 ChemSpider CHEBI:15345 ChEBI 1195 PubChem-compound CHEBI:17407 ChEBI 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 C00418 KEGG 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 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 HMDB01484 HMDB Delta(14)-sterol reductase 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 Reaction6923 false 5α-cholesta-8,24-dien-3-one + Hydrogen Ion + NADPH → NADP + Zymosterol LEFT_TO_RIGHT 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 2.1.1.41 false 2.1.1.41 S-Adenosylmethionine + Zymosterol → Hydrogen Ion + S-Adenosylhomocysteine + fecosterol LEFT_TO_RIGHT 1.0 SMILES CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O 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 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol (S)-5-Diphosphomevalonic acid NADP HMDB01377 HMDB CHEBI:1307929 ChEBI Cholesterol biosynthesis and metabolism CE(18:0) 1061 PubChem-compound 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 1.1.1.270 false 1.1.1.270 3-Keto-4-methylzymosterol + Hydrogen Ion + NADPH → 4a-Methylzymosterol + NADP 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 HMDB01375 HMDB 24762165 PubChem-compound 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 11975273 PubChem-compound