Quantitative metabolomics services for biomarker discovery and validation.
Specializing in ready to use metabolomics kits.
Your source for quantitative metabolomics technologies and bioinformatics.
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Small Molecule Pathway Database.
Loading Pathway...
C28H46O 4a-Methylzymosterol 398.35486 HMDB01343 HMDB HMDB00256 HMDB 388357 ChemSpider 6022 PubChem-compound C28H44O Ergosterol 396.3392 HMDB01347 HMDB Farnesyl pyrophosphate C23H38N7O17P3S Acetyl-CoA 809.1258 1.0 PW002482 PathWhiz 937 ChemSpider 1.0 MEVALONATE BioCyc HMDB00250 HMDB 1.0 388353 ChemSpider HMDB01341 HMDB Lanosterol 14-alpha demethylase CHOLESTEROL BioCyc 1.0 1.0 1.0 P08524 UniProt C00448 KEGG Compound PW000054 PathWhiz SubPathwayInteraction3759 SubPathway3759Reaction SubPathwayReaction SubPathwayInteraction3757 SubPathway3757Reaction SubPathwayReaction ReactionCatalysis6580 ACTIVATION SubPathwayInteraction3758 SubPathwayReaction SubPathway3758Reaction SubPathwayInteraction3755 SubPathwayReaction SubPathway3755Reaction 111-02-4 CAS SubPathwayInteraction3756 SubPathway3756Reaction SubPathwayReaction NADPH SubPathwayInteraction3753 SubPathwayReaction SubPathway3753Reaction ATP BioCyc SubPathwayInteraction3754 SubPathway3754Reaction SubPathwayReaction P25087 UniProt SubPathwayInteraction3752 SubPathwayReaction SubPathway3752Reaction HMDB00142 HMDB PW000051 PathWhiz C15816 KEGG Compound 1.0 1.0 559142 ChemSpider 440371 PubChem-compound 2.0 Unknown http://identifiers.org/smpdb/SMP00035 SMPDB Mevalonic acid P54781 UniProt http://identifiers.org/smpdb/SMP00032 SMPDB CHEBI:28113 ChEBI C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 5α-cholesta-8,24-dien-3-one C15H23N6O5S S-Adenosylmethionine 399.14505 4α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol 4β-methyl-4α-carboxy-cholesta-8,24-dien-3β-ol 4α-carboxy-5α-cholesta-8,24-dien-3β-ol HMDB01206 HMDB 4α-formyl-5α-cholesta-8,24-dien-3β-ol 90657655 PubChem-compound 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 Steroid Biosynthesis PW000163 PathWhiz 2.0 1.0 C00332 KEGG Compound CHEBI:16474 ChEBI P10614 UniProt 1.0 952 ChemSpider Carbon dioxide HMDB59597 HMDB 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 4α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol EPOXYSQUALENE BioCyc (S)-2,3-Epoxysqualene 4a-Methylzymosterol HMDB01217 HMDB C00341 KEGG Compound BiologicalState210 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum BiologicalState213 Saccharomyces cerevisiae, Cell, Endoplasmic Reticulum Membrane CHEBI:17211 ChEBI 445713 PubChem-compound 1010 ChemSpider Ergosterol BiologicalState216 Saccharomyces cerevisiae, Cell, Peroxisome 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 http://identifiers.org/smpdb/SMP00051 SMPDB PPI BioCyc 1.0 Lanosterin Pyrophosphate 23724571 PubChem-compound 57-87-4 CAS 1.0 HMDB01423 HMDB 1.0 ReactionCatalysis6891 ACTIVATION ReactionCatalysis6890 ACTIVATION Hydrogen Ion 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 C14H20N6O5S S-Adenosylhomocysteine 384.12158 2.3.1.9 false 2.3.1.9 2 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE C10H20O7P2 Geranyl-PP 314.06842 ReactionCatalysis6895 ACTIVATION ReactionCatalysis6894 ACTIVATION ReactionCatalysis6893 ACTIVATION ReactionCatalysis6892 ACTIVATION ReactionCatalysis6899 ACTIVATION ReactionCatalysis6898 ACTIVATION ReactionCatalysis6897 ACTIVATION ReactionCatalysis6896 ACTIVATION C00009 KEGG Compound HMDB00221 HMDB C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider C00007 KEGG Compound C00006 KEGG Compound HMDB00227 HMDB C5H12O7P2 Dimethylallylpyrophosphate 246.00583 CHEBI:18009 ChEBI C29H48O 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 412.3705 1.0 C00001 KEGG Compound NADP C01694 KEGG Compound ERGOSTEROL BioCyc CHEBI:18361 ChEBI C00005 KEGG Compound CHEBI:18367 ChEBI 10477914 ChemSpider 1032 ChemSpider CHEBI:18364 ChEBI C00002 KEGG Compound P15496 UniProt 150-97-0 CAS Tryptophan Metabolism SubPathway HMDB01429 HMDB C-3 sterol dehydrogenase Geranyl-PP 1.0 57-88-5 CAS Methylsterol monooxygenase C00019 KEGG Compound C01107 KEGG Compound C30H50O Lanosterin 426.38617 1.0 763-10-0 CAS Adenosine triphosphate C00011 KEGG Compound C00010 KEGG Compound 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 24,25-Dihydrolanosterol 388531 ChemSpider C00013 KEGG Compound 3.0 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 2.0 NAD(P) BioCyc 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc 1.0 Reaction6886 false 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 388301 ChemSpider S-Adenosylhomocysteine 1.0 CHEBI:1949 ChEBI 445995 PubChem-compound 56-65-5 CAS 443212 PubChem-compound C00021 KEGG Compound 11090531 PubChem-compound C00024 KEGG Compound 1.0 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc 2.0 1.0 http://identifiers.org/smpdb/SMP00130 SMPDB CPD-499 BioCyc 647 PubChem-compound P27796 UniProt 388517 ChemSpider CL:0000000 CELL TYPE ONTOLOGY 372-97-4 CAS 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 Peroxisome Water Mevalonic acid-5P 1.0 SMILES [O-]P([O-])(=O)OP([O-])([O-])=O GERANYL-PP BioCyc 22298941 PubChem-compound 22298942 PubChem-compound 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 Lanosterol synthase SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O 5.3.3.2 false 5.3.3.2 Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate REVERSIBLE HMDB00538 HMDB Reaction6891 false Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate LEFT_TO_RIGHT Mevalonic acid 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 22298940 PubChem-compound 1.3.1.72 false 1.3.1.72 Lanosterin + NADPH ↔ 24,25-Dihydrolanosterol + NADP REVERSIBLE 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 1.0 C00058 KEGG Compound 436 ChemSpider Water 9029-62-3 CAS SMILES CC(O)(CCO)CC(O)=O 44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET BioCyc FORMATE BioCyc 46173808 PubChem-compound Adenosine diphosphate 3-keto sterol reductase Sterol 24-C-methyltransferase C-8 sterol isomerase CPD-4211 BioCyc C-5 sterol desaturase C10H16N5O13P3 Adenosine triphosphate 506.99576 SMILES CCCCC CPD-4578 BioCyc C00187 KEGG Compound Episterol 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 Pyrophosphate 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 Steroidogenesis SubPathway C30H52O 24,25-Dihydrolanosterol 428.40182 HMDB00878 HMDB HMDB01967 HMDB Bile Acid Biosynthesis SubPathway C-22 sterol desaturase C-24 sterol reductase 962 PubChem-compound Farnesyl pyrophosphate synthase 31983 ChemSpider 7448-03-5 CAS 5800 ChemSpider 1.0 53477900 PubChem-compound 3-Hydroxy-3-methylglutaryl-CoA CO2 Carbon dioxide 43.98983 1.0 Coenzyme A C00080 KEGG Compound SMILES O=O 1.0 1.0 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 Delta(14)-sterol reductase 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 Squalene 58-64-0 CAS C01054 KEGG Compound 21865764 ChemSpider 3-ketoacyl-CoA thiolase, peroxisomal 1.0 1.0 C28H46O fecosterol 398.35486 ergosta-5,7,22,24(28)-tetraen-3-β-ol 1.0 C28H44O 5,7,24(28)-Ergostatrienol 396.3392 5,7,24(28)-Ergostatrienol C27H44O Zymosterol 384.3392 fecosterol C28H42O ergosta-5,7,22,24(28)-tetraen-3-β-ol 394.32358 Zymosterol 1.0 644102 PubChem-compound 4932 TAXONOMY 444493 PubChem-compound SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 64-18-6 CAS 4,4-Dimethylcholesta-8,14,24-trienol 22833512 PubChem-compound 25246222 PubChem-compound ACETYL-COA BioCyc Unknown H2O Water 18.010565 22212495 PubChem-compound 1.0 2.0 29908-03-0 CAS Lanosterin HMDB00961 HMDB Squalene synthase 977 PubChem-compound Carbon dioxide 627 ChemSpider P25340 UniProt squalene monooxygenase P29704 UniProt Isopentenyl pyrophosphate 17215925 ChemSpider 4.0 P38604 UniProt Methylsterol monooxygenase C-3 sterol dehydrogenase CHEBI:16933 ChEBI SMILES O C6H12O4 Mevalonic acid 148.07356 CHEBI:16928 ChEBI SQUALENE BioCyc 3425 PubChem-compound Fatty acid Metabolism SubPathway 92746 PubChem-compound 1.0 393270 ChemSpider ReactionCatalysis6900 ACTIVATION 6816 PubChem-compound Water C27H46O Cholesterol 386.35486 ADP BioCyc 90659076 PubChem-compound HMDB00939 HMDB Dimethylallylpyrophosphate 1553-55-5 CAS Isopentenyl-diphosphate Delta-isomerase 53-59-8 CAS 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 Butyrate Metabolism SubPathway 1.0 C05109 KEGG Compound C05108 KEGG Compound 1038 PubChem-compound C05103 KEGG Compound ferrocytochrome c ferricytochrome c 79-63-0 CAS 1.0 (S)-5-Diphosphomevalonic acid 3.0 278 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 1.0 CHEBI:505093 ChEBI ADENOSYL-HOMO-CYS BioCyc CPD-641 BioCyc O4P Phosphate 94.95342 NADPH 1.0 1.0 Adenosine triphosphate NADP 25994967 ChemSpider C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 Acetyl-CoA SubPathwayOutput Geranylgeranyl pyrophosphate synthase 90659175 PubChem-compound NADPH BioCyc 449 PubChem-compound Mevalonic acid-5P 50990081 PubChem-compound C5H12O7P2 Isopentenyl pyrophosphate 246.00583 CPD-6641 BioCyc SMILES [O-]P([O-])([O-])=O P24521 UniProt Oxygen 124-38-9 CAS 1.0 mevalonate kinase 6.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 1.0 Oxygen CHEBI:15414 ChEBI P32377 UniProt 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 CHEBI:15899 ChEBI 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 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 1.0 393471 ChemSpider 53-57-6 CAS CPD-8606 BioCyc Lanosterol synthase squalene monooxygenase 1.0 1.0 Delta(14)-sterol reductase Lanosterol 14-alpha demethylase Isopentenyl-diphosphate Delta-isomerase Diphosphomevalonate decarboxylase SMILES O=C=O S-ADENOSYLMETHIONINE BioCyc Squalene synthase Farnesyl pyrophosphate synthase Phosphomevalonate kinase O7P2 Pyrophosphate 173.91193 C25H40N7O18P3S Acetoacetyl-CoA 851.13635 1.0 4-METHYL-824-CHOLESTADIENOL BioCyc Acetoacetyl-CoA SubPathwayOutput 1.0 5957 PubChem-compound 439418 PubChem-compound C30H50 Squalene 410.39127 Cholesterol SubPathwayInput 1.0 P53199 UniProt CHEBI:17813 ChEBI (S)-2,3-Epoxysqualene CHEBI:15991 ChEBI 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 439400 PubChem-compound C10H15N5O10P2 Adenosine diphosphate 427.02942 HMDB01090 HMDB GO:0005737 GENE ONTOLOGY 11025495 PubChem-compound C6H13O7P Mevalonic acid-5P 228.03989 79-62-9 CAS P12684 UniProt Coenzyme A P12683 UniProt P53045 UniProt Endoplasmic Reticulum Endoplasmic Reticulum Membrane CPD-8587 BioCyc HMDB01185 HMDB HMDB01188 HMDB CHEBI:15441 ChEBI 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 ReactionCatalysis6859 ACTIVATION CHEBI:1146900 ChEBI ReactionCatalysis6858 ACTIVATION ReactionCatalysis6857 ACTIVATION ReactionCatalysis6856 ACTIVATION 1.0 1.0 P32462 UniProt 14000-31-8 CAS P07277 UniProt CO-A BioCyc Adenosine diphosphate 1.0 LANOSTEROL BioCyc 5675 ChemSpider 72-89-9 CAS 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 ReactionCatalysis6867 ACTIVATION ReactionCatalysis6862 ACTIVATION 18971002 PubChem-compound Cytoplasm ReactionCatalysis6861 ACTIVATION ReactionCatalysis6860 ACTIVATION ReactionCatalysis6866 ACTIVATION 1.0 ReactionCatalysis6865 ACTIVATION ReactionCatalysis6864 ACTIVATION Cell ReactionCatalysis6863 ACTIVATION 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol ACETOACETYL-COA BioCyc 1.0 CHEBI:15422 ChEBI Farnesyl pyrophosphate synthase 6557 ChemSpider 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 HMDB01285 HMDB 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 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 1.0 3-ketoacyl-CoA thiolase, peroxisomal 440560 PubChem-compound 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 Isopentenyl pyrophosphate 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 391478 ChemSpider 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@@]([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 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 1.0 73566-35-5 CAS CHEBI:16761 ChEBI 7782-44-7 CAS 1.0 246983 PubChem-compound ReactionCatalysis6889 ACTIVATION 90658366 PubChem-compound GO:0005777 GENE ONTOLOGY ReactionCatalysis6882 ACTIVATION Dimethylallylpyrophosphate 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 21775588 PubChem-compound 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 PW000145 PathWhiz Farnesyl pyrophosphate C01724 KEGG Compound PW000023 PathWhiz 358-71-4 CAS HMDB06839 HMDB HMDB06838 HMDB 392413 ChemSpider (S)-5-Diphosphomevalonic acid 1.0 Diphosphomevalonate decarboxylase PW000141 PathWhiz 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 http://identifiers.org/smpdb/SMP00060 SMPDB CHEBI:30751 ChEBI 3-Hydroxy-3-methylglutaryl-CoA 1420-36-6 CAS http://identifiers.org/smpdb/SMP00063 SMPDB CHEBI:15377 ChEBI HMDB00067 HMDB CHEBI:17436 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] Phosphomevalonate kinase Unknown HMDB06847 HMDB PW000014 PathWhiz 3-hydroxy-3-methylglutaryl-coenzyme A reductase 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 1.0 Phosphate S-Adenosylmethionine CHEBI:16584 ChEBI SMILES C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3 SMILES [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])CC3 1.0 9200676 ChemSpider 3.0 http://identifiers.org/smpdb/SMP00073 SMPDB 280 PubChem-compound BiologicalState198 Saccharomyces cerevisiae, Cell, Cytoplasm 1.0 CHEBI:15467 ChEBI 30776536 ChemSpider CHEBI:15345 ChEBI 1195 PubChem-compound Pyruvate Metabolism SubPathway CHEBI:17407 ChEBI C00418 KEGG Compound 1.0 Valine, Leucine and Isoleucine Degradation SubPathway 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 mevalonate kinase 389460 ChemSpider 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 HMDB01484 HMDB http://identifiers.org/smpdb/SMP02381 SMPDB 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 1.0 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 SMILES CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O 1.0 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 NADP HMDB01377 HMDB CHEBI:1307929 ChEBI 1061 PubChem-compound 1.0 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 1.0 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 Formic acid 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 11975273 PubChem-compound Endoplasmic Reticulum Hydroxymethylglutaryl- CoA synthase 3-ketoacyl-CoA thiolase, peroxisomal Mevalonate kinase Phosphomevalonate kinase Diphosphomevalonate decarboxylase Isopentenyl- diphosphate Delta-isomerase 1 Farnesyl pyrophosphate synthase Geranylgeranyl pyrophosphate synthase Farnesyl pyrophosphate synthase Geranylgeranyl pyrophosphate synthase Squalene synthase Squalene monooxygenase Lanosterol