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C-24 sterol reductase C28H46O 4a-Methylzymosterol 398.35486 3.0 C28H44O Ergosterol 396.3392 388357 ChemSpider 6022 PubChem-compound 1.0 C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc 388353 ChemSpider CHOLESTEROL BioCyc HMDB0001185 HMDB HMDB0001188 HMDB P08524 UniProt C00448 KEGG Compound 389458 ChemSpider 4a-Methylzymosterol 111-02-4 CAS ATP BioCyc P25087 UniProt C15816 KEGG Compound 559142 ChemSpider 440371 PubChem-compound Mevalonic acid P54781 UniProt C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 CHEBI:16113 ChEBI Sterol 24-C-methyltransferase C15H23N6O5S S-Adenosylmethionine 399.14505 90657655 PubChem-compound 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 1.0 CHEBI:16474 ChEBI C00332 KEGG Compound P10614 UniProt 952 ChemSpider Ergosterol fecosterol 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 EPOXYSQUALENE BioCyc HMDB0001090 HMDB 1.0 C00341 KEGG Compound Isopentenyl pyrophosphate CHEBI:17211 ChEBI Cholesterol 445713 PubChem-compound 1010 ChemSpider 1.0 Saccharomyces cerevisiae 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@@H](O)C(=O)NCCC(=O)NCCS 1.0 PPI BioCyc P41338 UniProt 1.0 ReactionCatalysis6485 ACTIVATION 57-87-4 CAS 23724571 PubChem-compound ReactionCatalysis6891 ACTIVATION ReactionCatalysis6890 ACTIVATION 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=C1N=CN=C2N 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 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 C00009 KEGG Compound C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider HMDB0062389 HMDB 1.0 C00007 KEGG Compound C00006 KEGG Compound 5a-cholesta-7,24-dien-3B-ol 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 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 long-chain fatty acyl-CoA C00019 KEGG Compound C01107 KEGG Compound C30H50O Lanosterin 426.38617 1.0 763-10-0 CAS C00011 KEGG Compound C00010 KEGG Compound P54839 UniProt CHEBI:17002 ChEBI 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 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 445995 PubChem-compound 11090531 PubChem-compound 56-65-5 CAS 443212 PubChem-compound C00021 KEGG Compound 5775 ChemSpider 388662 ChemSpider C00024 KEGG Compound 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc 3-keto sterol reductase CPD-499 BioCyc 647 PubChem-compound 388517 ChemSpider 372-97-4 CAS 1.0 1.0 C28H46O Episterol 398.35486 HMDB0001343 HMDB 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 HMDB0000256 HMDB HMDB0001347 HMDB HMDB0000250 HMDB 1.0 1.0 SMILES [O-]P([O-])(=O)OP([O-])([O-])=O HMDB0001341 HMDB GERANYL-PP BioCyc Squalene 22298941 PubChem-compound 22298942 PubChem-compound 3-Keto-4-methylzymosterol Cholesteryl ester 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 HMDB0003896 HMDB SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O 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 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 HMDB0000142 HMDB 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 HMDB0060404 HMDB FORMATE BioCyc 46173808 PubChem-compound HMDB0001120 HMDB 2.3.1.9 false 2.3.1.9 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE HMDB0001484 HMDB 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 HMDB0001377 HMDB 2.0 SMILES [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)C C28H44O 3-Keto-4-methylzymosterol 396.3392 HMDB0001251 HMDB HMDB0001375 HMDB 962 PubChem-compound 31983 ChemSpider 7448-03-5 CAS 1.0 5800 ChemSpider 53477900 PubChem-compound CO2 Carbon dioxide 43.98983 Coenzyme A C00080 KEGG Compound SMILES O=O HMDB0006838 HMDB CHEBI:27910 ChEBI squalene monooxygenase Squalene synthase long-chain fatty acyl-CoA 4α-carboxy-5α-cholesta-8,24-dien-3β-ol HMDB0002111 HMDB 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 HMDB0001023 HMDB PW071057 PathWhiz 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 HMDB0006847 HMDB C27H44O Desmosterol 384.3392 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol HMDB0000067 HMDB C28H46O fecosterol 398.35486 C28H44O 5,7,24(28)-Ergostatrienol 396.3392 C27H44O Zymosterol 384.3392 C28H42O ergosta-5,7,22,24(28)-tetraen-3-β-ol 394.32358 acetyl-CoA C-acetyltransferase 1.0 (S)-2,3-Epoxysqualene 644102 PubChem-compound 4932 TAXONOMY 444493 PubChem-compound Acetyl-CoA 1.0 SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 64-18-6 CAS 1.0 Cholesterol Biosynthesis and Metabolism 22833512 PubChem-compound 25246222 PubChem-compound C-8 sterol isomerase ACETYL-COA BioCyc Mevalonic acid-5P H2O Water 18.010565 22212495 PubChem-compound HMDB0001285 HMDB ReactionCatalysis7248 ACTIVATION HMDB0001286 HMDB 2.0 ReactionCatalysis7250 ACTIVATION 1.0 977 PubChem-compound HMDB0059597 HMDB ReactionCatalysis7251 ACTIVATION 2.0 627 ChemSpider P25340 UniProt 1.0 1.0 5a-cholesta-7,24-dien-3B-ol P29704 UniProt 17215925 ChemSpider 7-Dehydrodesmosterol P38604 UniProt CHEBI:16933 ChEBI ferricytochrome c 1.0 CPD-4141 BioCyc SMILES O 3.0 C6H12O4 Mevalonic acid 148.07356 CHEBI:16928 ChEBI C-5 sterol desaturase SQUALENE BioCyc HMDB0000538 HMDB 3425 PubChem-compound 1.0 92746 PubChem-compound Methylsterol monooxygenase HMDB0002719 HMDB 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 90659076 PubChem-compound Dimethylallylpyrophosphate 53-59-8 CAS 1553-55-5 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 C05107 KEGG Compound 1.0 1038 PubChem-compound C05108 KEGG Compound 5997 PubChem-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 485-80-3 CAS Lanosterin SMP0070041 SMPDB 25994967 ChemSpider Hydrogen Ion C21H30N7O17P3 NADPH 745.0911 mevalonate kinase C21H29N7O17P3 NADP 744.08325 90659175 PubChem-compound Episterol NADPH BioCyc 449 PubChem-compound 50990081 PubChem-compound C5H12O7P2 Isopentenyl pyrophosphate 246.00583 CPD-6641 BioCyc HMDB0001423 HMDB SMILES [O-]P([O-])([O-])=O 5α-cholesta-8,24-dien-3-one HMDB0000217 HMDB P24521 UniProt 124-38-9 CAS 1.0 mevalonate kinase 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 CHEBI:15414 ChEBI P32377 UniProt 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 CHEBI:15899 ChEBI HMDB0001429 HMDB 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 HMDB0000221 HMDB 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 HMDB0000227 HMDB 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 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 HMDB0001206 HMDB 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 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 439400 PubChem-compound Farnesyl pyrophosphate C10H15N5O10P2 Adenosine diphosphate 427.02942 C6H13O7P Mevalonic acid-5P 228.03989 HMDB0001217 HMDB P12684 UniProt Reaction119907 false Cholesterol + long-chain fatty acyl-CoA ↔ Cholesteryl ester + Coenzyme A REVERSIBLE 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 Endoplasmic Reticulum CPD-8587 BioCyc Adenosine diphosphate 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 HMDB0000939 HMDB ReactionCatalysis6869 ACTIVATION ReactionCatalysis6868 ACTIVATION C21H36N7O16P3S Coenzyme A 767.11523 Water S-Adenosylmethionine ReactionCatalysis6862 ACTIVATION 18971002 PubChem-compound 1.0 ReactionCatalysis6860 ACTIVATION ReactionCatalysis6866 ACTIVATION ReactionCatalysis6865 ACTIVATION ReactionCatalysis6864 ACTIVATION ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI Phosphomevalonate kinase 6557 ChemSpider 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 HMDB0062392 HMDB 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 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 1.0 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 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 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:17737 ChEBI 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 HMDB0000961 HMDB 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 358-71-4 CAS Cholesteryl ester 392413 ChemSpider 1.0 1715-86-2 CAS C00751 KEGG Compound 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 CHEBI:17436 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] Acetoacetyl-CoA C5H12 ferrocytochrome c 72.0939 3-hydroxy-3-methylglutaryl-coenzyme A reductase 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 CHEBI:16584 ChEBI 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 SMILES C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3 280 PubChem-compound 1.0 Phosphate CHEBI:15467 ChEBI 30776536 ChemSpider CHEBI:15345 ChEBI 1195 PubChem-compound CHEBI:17407 ChEBI 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 SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O Diphosphomevalonate decarboxylase 1.0 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 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 HMDB0000878 HMDB HMDB0001967 HMDB 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 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 Endoplasmic Reticulum acetyl-CoA C- acetyltransferase Hydroxymethylglutaryl- CoA synthase mevalonate kinase Phosphomevalonate kinase Diphosphomevalonate decarboxylase Isopentenyl- diphosphate Delta-isomerase Farnesyl pyrophosphate synthase Farnesyl pyrophosphate synthase Squalene synthase squalene monooxygenase Lanosterol synthase Lanosterol 14-alpha demethylase Delta(14)- sterol reductase Methylsterol monooxygenase Methylsterol monooxygenase Methylsterol monooxygenase C-3 sterol dehydrogenase 3-keto sterol reductase Methylsterol monooxygenase Methylsterol monooxygenase Methylsterol monooxygenase C-3 sterol dehydrogenase 3-keto sterol reductase Sterol 24-C- methyltransferase C-8 sterol isomerase C-5 sterol desaturase C-22 sterol desaturase C-24 sterol reductase C-8 sterol isomerase C-5 sterol desaturase 3-hydroxy-3- methylglutaryl- coenzyme A reductase 2 Desmosterol Cholesterol Acetyl-CoA CoA Acetoacetyl-CoA Acetyl-CoA H 2 O 3-Hydroxy-3- methylglutaryl- CoA CoA NADPH Mevalonic acid NADP CoA ATP