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C-24 sterol reductase 3.0 1.0 mevalonate kinase (S)-5-Diphosphomevalonic acid 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 Isopentenyl-diphosphate Delta-isomerase Farnesyl pyrophosphate synthase Squalene synthase 1.0 squalene monooxygenase Phosphomevalonate kinase Diphosphomevalonate decarboxylase P08524 UniProt C00448 KEGG Compound HMDB03896 HMDB NADPH P25087 UniProt HMDB00142 HMDB 559142 ChemSpider 440371 PubChem-compound BTO:0000759 BRENDA TISSUE ONTOLOGY HMDB01206 HMDB 90657655 PubChem-compound 1.0 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 2.0 CHEBI:16474 ChEBI P10614 UniProt 1.0 HMDB01217 HMDB BiologicalState210 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum 7-Dehydrodesmosterol BiologicalState213 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum Membrane Isopentenyl pyrophosphate BiologicalState212 Saccharomyces cerevisiae, Liver, Cell, Endoplasmic Reticulum Membrane 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 1.0 P41338 UniProt 23724571 PubChem-compound 57-87-4 CAS 1.0 HMDB01423 HMDB Hydrogen Ion 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 1989-52-2 CAS C00235 KEGG Compound CHEBI:16057 ChEBI Adenosine triphosphate Geranyl-PP 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 C00001 KEGG Compound NADP 1.0 C00005 KEGG Compound 10477914 ChemSpider C00002 KEGG Compound P15496 UniProt 150-97-0 CAS HMDB01429 HMDB 1.0 1.0 3130-72-1 CAS C00019 KEGG Compound C01107 KEGG Compound 1.0 C00011 KEGG Compound Dimethylallylpyrophosphate C00010 KEGG Compound 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 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 Coenzyme A 56-65-5 CAS 443212 PubChem-compound C00021 KEGG Compound 11090531 PubChem-compound 388662 ChemSpider C00024 KEGG Compound 1.0 CL:0000000 CELL TYPE ONTOLOGY 1.0 3-Hydroxy-3-methylglutaryl-CoA SMILES CC(C)=CCC\C(C)=C/CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 1.0 1.0 GERANYL-PP BioCyc 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 Reaction6892 false Geranyl-PP + Isopentenyl pyrophosphate → Farnesyl pyrophosphate + Pyrophosphate LEFT_TO_RIGHT 1.0 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 C00058 KEGG Compound 1.0 436 ChemSpider 9029-62-3 CAS SMILES CC(O)(CCO)CC(O)=O 1.0 2.0 FORMATE BioCyc 46173808 PubChem-compound 3-keto sterol reductase CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 FARNESYL-PP BioCyc 1.0 C27H42O 7-Dehydrodesmosterol 382.32358 2.0 962 PubChem-compound 31983 ChemSpider 1.0 CO2 Carbon dioxide 43.98983 1.0 Phosphate Coenzyme A 1.0 C00080 KEGG Compound C41H72O2 CE(14:0) 596.5532 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 14265-44-2 CAS 21865764 ChemSpider (S)-2,3-Epoxysqualene 1.0 644102 PubChem-compound Mevalonic acid 1.0 1.0 SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 64-18-6 CAS Acetyl-CoA 1.0 ReactionCatalysis7249 ACTIVATION ReactionCatalysis7248 ACTIVATION 29908-03-0 CAS ReactionCatalysis7250 ACTIVATION HMDB00961 HMDB 977 PubChem-compound ReactionCatalysis7251 ACTIVATION Carbon dioxide 627 ChemSpider Lanosterol synthase Lanosterol 14-alpha demethylase Delta(14)-sterol reductase 17215925 ChemSpider Hydroxymethylglutaryl-CoA synthase P38604 UniProt Methylsterol monooxygenase C-3 sterol dehydrogenase 1.0 89882 ChemSpider 1.0 Acetoacetyl-CoA 3.0 99486 PubChem-compound 1.0 Methylsterol monooxygenase ReactionCatalysis6900 ACTIVATION 6816 PubChem-compound C27H46O Cholesterol 386.35486 1.0 C05107 KEGG Compound Farnesyl pyrophosphate synthase C05108 KEGG Compound Farnesyl pyrophosphate synthase C05103 KEGG Compound 79-63-0 CAS 278 ChemSpider C-22 sterol desaturase C-5 sterol desaturase 274 ChemSpider C-24 sterol reductase Phosphomevalonate kinase 3-keto sterol reductase C-8 sterol isomerase Sterol 24-C-methyltransferase CPD-641 BioCyc 1.0 O4P Phosphate 94.95342 3-hydroxy-3-methylglutaryl-coenzyme A reductase Lanosterin 25994967 ChemSpider 2.0 Hydrogen Ion 90659175 PubChem-compound 5a-cholesta-7,24-dien-3B-ol NADPH BioCyc 50990081 PubChem-compound CPD-6641 BioCyc SMILES [O-]P([O-])([O-])=O Formic acid 1.0 mevalonate kinase 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 CHEBI:15532 ChEBI 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 NADPH Liver Episterol 474-68-0 CAS C35H62N7O17P3S Tetradecanoyl-CoA 977.3136 Geranyl-PP Lanosterol synthase squalene monooxygenase 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 SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCC)[C@H](C)CCCC(C)C 5957 PubChem-compound 1.0 P53199 UniProt Reaction989 false 7-Dehydrodesmosterol → Desmosterol LEFT_TO_RIGHT (S)-5-Diphosphomevalonic acid 1.0 CHEBI:15991 ChEBI HMDB01090 HMDB 11025495 PubChem-compound P12684 UniProt P12683 UniProt C01802 KEGG Compound 4,4-Dimethylcholesta-8,14,24-trienol P32462 UniProt 14000-31-8 CAS P07277 UniProt CO-A BioCyc LANOSTEROL BioCyc 1.0 5675 ChemSpider 72-89-9 CAS 216175 ChemSpider SMILES C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O Water Cell 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 1.0 6557 ChemSpider 1.0 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol HMDB01285 HMDB CHEBI:50586 ChEBI 1.0 HMDB01286 HMDB 1.0 CHEBI:25351 ChEBI CH2O2 Formic acid 46.005478 1.0 439577 PubChem-compound GO:0005789 GENE ONTOLOGY GO:0005783 GENE ONTOLOGY 1.0 CHEBI:17737 ChEBI 1.0 P32476 UniProt Formic acid 440558 PubChem-compound 7782-44-7 CAS Lanosterol 14-alpha demethylase 21775588 PubChem-compound Farnesyl pyrophosphate 1.0 358-71-4 CAS 392413 ChemSpider 1.0 1.0 1.0 C00751 KEGG Compound HMDB01023 HMDB HMDB02111 HMDB CHEBI:30751 ChEBI 3.0 CHEBI:15377 ChEBI 1.0 HMDB06725 HMDB CHEBI:15379 ChEBI (S)-2,3-Epoxysqualene CHEBI:15378 ChEBI SMILES [H+] 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 Mevalonic acid-5P 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 9200676 ChemSpider BiologicalState195 Saccharomyces cerevisiae, Endoplasmic Reticulum 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 30776536 ChemSpider CHEBI:15345 ChEBI 1195 PubChem-compound Farnesyl pyrophosphate synthase 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 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 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 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 1.0 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 Isopentenyl pyrophosphate 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 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 CHEBI:84304 ChEBI C28H46O 4a-Methylzymosterol 398.35486 HMDB01343 HMDB HMDB00256 HMDB 388357 ChemSpider 6022 PubChem-compound C28H44O Ergosterol 396.3392 HMDB01347 HMDB 1.0 C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc HMDB00250 HMDB Hydroxymethylglutaryl-CoA synthase 388353 ChemSpider 1.0 HMDB01341 HMDB CHOLESTEROL BioCyc 1.0 1.0 389458 ChemSpider 4a-Methylzymosterol 1.0 111-02-4 CAS ATP BioCyc Lanosterin C15816 KEGG Compound 1.0 Mevalonic acid P54781 UniProt C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 5α-cholesta-8,24-dien-3-one C15H23N6O5S S-Adenosylmethionine 399.14505 1.0 4α-carboxy-5α-cholesta-8,24-dien-3β-ol Adenosine diphosphate 1.0 1.0 C00332 KEGG Compound Hydrogen Ion 952 ChemSpider HMDB59597 HMDB Ergosterol 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol EPOXYSQUALENE BioCyc (S)-2,3-Epoxysqualene 4a-Methylzymosterol Acetyl-CoA C00341 KEGG Compound Tetradecanoyl-CoA CHEBI:17211 ChEBI Cholesterol 445713 PubChem-compound 2.0 Dimethylallylpyrophosphate 1010 ChemSpider 4.0 PPI BioCyc ReactionCatalysis6485 ACTIVATION Pyrophosphate 1.0 ReactionCatalysis6891 ACTIVATION ReactionCatalysis6890 ACTIVATION 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 1.0 C00356 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 1.0 C14H20N6O5S S-Adenosylhomocysteine 384.12158 1.0 C10H20O7P2 Geranyl-PP 314.06842 ReactionCatalysis6895 ACTIVATION ReactionCatalysis6894 ACTIVATION ReactionCatalysis6893 ACTIVATION ReactionCatalysis6892 ACTIVATION ReactionCatalysis6899 ACTIVATION 1.0 ReactionCatalysis6898 ACTIVATION ReactionCatalysis6897 ACTIVATION C-22 sterol desaturase ReactionCatalysis6896 ACTIVATION HMDB00221 HMDB C00129 KEGG Compound 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 Farnesyl pyrophosphate 1032 ChemSpider CHEBI:18364 ChEBI 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 HMDB01521 HMDB 763-10-0 CAS 1.0 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol Geranyl-PP 388531 ChemSpider 2.0 NAD(P) BioCyc 1.0 Pyrophosphate 388301 ChemSpider 3.0 Lanosterol synthase 445995 PubChem-compound acetyl-CoA C-acetyltransferase 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc http://identifiers.org/smpdb/SMP02435 SMPDB 1.0 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 Water Adenosine triphosphate 22298941 PubChem-compound 22298942 PubChem-compound 1.0 C02593 KEGG Compound S-Adenosylmethionine C-3 sterol dehydrogenase 22298940 PubChem-compound C15H28O7P2 Farnesyl pyrophosphate 382.131 53477723 PubChem-compound 3.0 7732-18-5 CAS Water 44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET BioCyc 1.0 2.3.1.9 false 2.3.1.9 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE 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 3-Keto-4-methylzymosterol 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 7448-03-5 CAS 5800 ChemSpider 53477900 PubChem-compound 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1.0 CHEBI:27910 ChEBI 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 Squalene 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 Isopentenyl-diphosphate Delta-isomerase 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 Farnesyl pyrophosphate synthase 1.0 1.0 22833512 PubChem-compound 25246222 PubChem-compound ACETYL-COA BioCyc Mevalonic acid-5P H2O Water 18.010565 22212495 PubChem-compound 1.0 1.0 Squalene synthase 1.0 P25340 UniProt 1.0 1.0 squalene monooxygenase 2.0 1.0 P29704 UniProt SMILES CCCCCCCCCCCCCC(=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 7-Dehydrodesmosterol Acetoacetyl-CoA 65113 PubChem-compound CHEBI:16933 ChEBI CPD-4141 BioCyc 1.0 SMILES O Squalene Pyrophosphate C6H12O4 Mevalonic acid 148.07356 CHEBI:16928 ChEBI SQUALENE BioCyc 3425 PubChem-compound 92746 PubChem-compound 5,7,24(28)-Ergostatrienol 1.0 393270 ChemSpider ergosta-5,7,22,24(28)-tetraen-3-β-ol ADP BioCyc 90659076 PubChem-compound fecosterol 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 1.0 1038 PubChem-compound Mevalonic acid 3-keto sterol reductase CHEBI:505093 ChEBI ADENOSYL-HOMO-CYS BioCyc 1.0 1.0 1.0 NADPH NADP C21H30N7O17P3 NADPH 745.0911 mevalonate kinase C21H29N7O17P3 NADP 744.08325 1.0 449 PubChem-compound C5H12O7P2 Isopentenyl pyrophosphate 246.00583 Zymosterol 3-Hydroxy-3-methylglutaryl-CoA P24521 UniProt Oxygen 124-38-9 CAS ergosta-5,7,22,24(28)-tetraen-3-β-ol Oxygen CHEBI:15414 ChEBI P32377 UniProt CHEBI:15899 ChEBI Farnesyl pyrophosphate synthase 1.0 TETRADECANOYL-COA BioCyc 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 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 2.5.1.10,2.5.1.1 false 2.5.1.10,2.5.1.1 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate LEFT_TO_RIGHT 1.0 Reaction7267 false Desmosterol → Cholesterol LEFT_TO_RIGHT Reaction7266 false 5a-cholesta-7,24-dien-3B-ol → 7-Dehydrodesmosterol LEFT_TO_RIGHT Reaction7268 false Cholesterol + Tetradecanoyl-CoA ↔ CE(14:0) + Coenzyme A REVERSIBLE 393471 ChemSpider 53-57-6 CAS 1.0 S-ADENOSYLMETHIONINE BioCyc O7P2 Pyrophosphate 173.91193 4-METHYL-824-CHOLESTADIENOL BioCyc CE(14:0) 439418 PubChem-compound C30H50 Squalene 410.39127 CHEBI:17813 ChEBI Isopentenyl pyrophosphate 439400 PubChem-compound Adenosine diphosphate Mevalonic acid-5P 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 58623 ChemSpider 1.0 3.0 Endoplasmic Reticulum Endoplasmic Reticulum Membrane CPD-8587 BioCyc 1.0 HMDB01185 HMDB HMDB01188 HMDB CHEBI:15441 ChEBI 4.0 Adenosine diphosphate 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 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol ReactionCatalysis6855 ACTIVATION Coenzyme A ReactionCatalysis6869 ACTIVATION ReactionCatalysis6868 ACTIVATION C21H36N7O16P3S Coenzyme A 767.11523 ReactionCatalysis6862 ACTIVATION 1.0 18971002 PubChem-compound 1.0 ReactionCatalysis6866 ACTIVATION ReactionCatalysis6865 ACTIVATION ReactionCatalysis6864 ACTIVATION 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI 2.0 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 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 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 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 439218 PubChem-compound CHEBI:16521 ChEBI Q12452 UniProt 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 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 C-5 sterol desaturase CHEBI:16761 ChEBI 246983 PubChem-compound 1.0 ReactionCatalysis6889 ACTIVATION 90658366 PubChem-compound ReactionCatalysis6882 ACTIVATION 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 C-8 sterol isomerase 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 Cholesterol biosynthesis and metabolism CE(14:0) HMDB06838 HMDB 1715-86-2 CAS Sterol 24-C-methyltransferase 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 5α-cholesta-8,24-dien-3-one HMDB00067 HMDB CHEBI:17436 ChEBI 4,4-Dimethylcholesta-8,14,24-trienol HMDB06847 HMDB 5886 PubChem-compound CHEBI:16584 ChEBI Methylsterol monooxygenase SMILES C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3 1.0 280 PubChem-compound Phosphate PW002544 PathWhiz CHEBI:15467 ChEBI CHEBI:17407 ChEBI C00418 KEGG Compound 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 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 1.0 ferrocytochrome c 1.0 NADP HMDB01377 HMDB 1061 PubChem-compound S-Adenosylhomocysteine ferricytochrome c HMDB01375 HMDB 24762165 PubChem-compound 11975273 PubChem-compound