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C28H46O 4a-Methylzymosterol 398.35486 HMDB01343 HMDB HMDB00256 HMDB 6022 PubChem-compound 388357 ChemSpider 1.0 HMDB01347 HMDB Farnesyl pyrophosphate C23H38N7O17P3S Acetyl-CoA 809.1258 P04035 UniProt 937 ChemSpider MEVALONATE BioCyc HMDB00250 HMDB Squalene monooxygenase 1.0 388353 ChemSpider HMDB01341 HMDB CHOLESTEROL BioCyc C15808 KEGG Compound SMP00023 SMPDB C00448 KEGG Compound 389458 ChemSpider HMDB03896 HMDB PW000054 PathWhiz HMDB06927 HMDB Lanosterol 14-alpha demethylase 1.0 111-02-4 CAS NADPH ATP BioCyc HMDB00142 HMDB PW000051 PathWhiz PW000050 PathWhiz C15816 KEGG Compound 1.0 3.1.1.13 false 3.1.1.13 Cholesterol + Fatty acid → Cholesterol Ester + Water LEFT_TO_RIGHT 4a-Methylzymosterol 1.0 559142 ChemSpider SMP00035 SMPDB Mevalonic acid Cholesterol Fatty acid SMP00032 SMPDB CHEBI:28113 ChEBI C11455 KEGG Compound C30H50O (S)-2,3-Epoxysqualene 426.38617 Cholesterol C03845 KEGG Compound 1.0 HMDB01206 HMDB P56937 UniProt 5742 ChemSpider C29H46O 4,4-Dimethylcholesta-8,14,24-trienol 410.35486 PW000163 PathWhiz 2.0 1.0 C00332 KEGG Compound CHEBI:16474 ChEBI 952 ChemSpider Carbon dioxide 1.0 EPOXYSQUALENE BioCyc (S)-2,3-Epoxysqualene 2.0 HMDB01217 HMDB 389550 ChemSpider C00341 KEGG Compound 7-Dehydrodesmosterol Steroid Biosynthesis CHEBI:17211 ChEBI 445713 PubChem-compound 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 SMP00051 SMPDB PPI BioCyc 1.0 Lanosterin Pyrophosphate HMDB01423 HMDB 1.0 Water 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 SubPathwayInteraction92 SubPathway92Reaction SubPathwayReaction Sterol O-acyltransferase 1 SubPathwayInteraction91 SubPathway91Reaction SubPathwayReaction SubPathwayInteraction96 SubPathwayReaction SubPathway96Reaction 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 C00356 KEGG Compound SubPathwayInteraction95 SubPathway95Reaction SubPathwayReaction CHEBI:16057 ChEBI SubPathwayInteraction94 SubPathway94Reaction SubPathwayReaction SubPathwayInteraction93 SubPathwayReaction SubPathway93Reaction Lysosomal acid lipase/cholesteryl ester hydrolase CHEBI:16290 ChEBI C10H20O7P2 Geranyl-PP 314.06842 3-Keto-4-methylzymosterol Q9BWD1 UniProt 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 Cholesterol C00009 KEGG Compound HMDB00221 HMDB C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider C00007 KEGG Compound C00249 KEGG Compound Diphosphomevalonate decarboxylase C00006 KEGG Compound 5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL BioCyc HMDB00227 HMDB C5H12O7P2 Dimethylallylpyrophosphate 246.00583 CHEBI:18009 ChEBI C29H48O 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol 412.3705 C00001 KEGG Compound NADP CHEBI:18361 ChEBI C00005 KEGG Compound CHEBI:18367 ChEBI 1032 ChemSpider CHEBI:18364 ChEBI C00002 KEGG Compound 150-97-0 CAS HMDB01429 HMDB P37268 UniProt 434-16-2 CAS Geranyl-PP 57-88-5 CAS ReactionCatalysis610 ACTIVATION ReactionCatalysis611 ACTIVATION 388534 ChemSpider BiologicalState49 C01107 KEGG Compound C30H50O Lanosterin 426.38617 ReactionCatalysis530 ACTIVATION 1.0 763-10-0 CAS SMILES [H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C Adenosine triphosphate C00011 KEGG Compound C00010 KEGG Compound 24,25-Dihydrolanosterol 388531 ChemSpider Squalene monooxygenase C00013 KEGG Compound 3.0 2.0 Delta(24)-sterol reductase NAD(P) BioCyc 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc Sterol O-acyltransferase 1 ReactionCatalysis527 ACTIVATION Lathosterol oxidase Acetyl-CoA acetyltransferase, cytosolic C6H14O10P2 (S)-5-Diphosphomevalonic acid 308.00623 Zymosterol intermediate 2 1.0 CHEBI:1949 ChEBI 445995 PubChem-compound 56-65-5 CAS 443212 PubChem-compound Lanosterol 14-alpha demethylase 388662 ChemSpider Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating C00024 KEGG Compound Squalene synthase Methylsterol monooxygenase 1 SubPathwayInteraction98 SubPathwayReaction SubPathway98Reaction Delta(14)-sterol reductase SubPathwayInteraction97 SubPathway97Reaction SubPathwayReaction Lathosterol oxidase 44-DIMETHYL-CHOLESTA-812-24-TRIENOL BioCyc ReactionCatalysis517 ACTIVATION 2.0 65728 PubChem-compound SMP00130 SMPDB Q15800 UniProt CPD-499 BioCyc 647 PubChem-compound 388517 ChemSpider P53602 UniProt C29H50O 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 414.38617 CL:0000000 CELL TYPE ONTOLOGY 372-97-4 CAS C27H46O 5a-Cholest-8-en-3b-ol 386.35486 C27H44O 5a-Cholesta-7,24-dien-3b-ol 384.3392 59151 ChemSpider SMILES CC(C)=CCC\C(C)=C/CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C HMDB61374 HMDB 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 Lanosterol synthase Mevalonic acid-5P Vitamin D3 1.0 HMDB61373 HMDB 114943 ChemSpider SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 1.0 GERANYL-PP BioCyc Farnesyl pyrophosphate synthase 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 3-keto-steroid reductase 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O 6.0 HMDB00538 HMDB Mevalonic acid 1.0 HMDB02719 HMDB C15H28O7P2 Farnesyl pyrophosphate 382.131 53477723 PubChem-compound 7448-02-4 CAS HMDB00876 HMDB 1.0 CHEBI:18252 ChEBI C01143 KEGG Compound Q15392 UniProt 7732-18-5 CAS CHEBI:17168 ChEBI 1.0 C00058 KEGG Compound 436 ChemSpider Water 9029-62-3 CAS 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(O)(CCO)CC(O)=O 44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET BioCyc FORMATE BioCyc Adenosine diphosphate SMILES [H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C 57-10-3 CAS 3-hydroxy-3-methylglutaryl-coenzyme A reductase 101770 PubChem-compound CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 CPD-4578 BioCyc C00187 KEGG Compound FARNESYL-PP BioCyc C27H42O 7-Dehydrodesmosterol 382.32358 Pyrophosphate BiologicalState18 70741-38-7 CAS 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 30792004 ChemSpider C28H44O 3-Keto-4-methylzymosterol 396.3392 C30H52O 24,25-Dihydrolanosterol 428.40182 HMDB01967 HMDB P38571 UniProt 962 PubChem-compound 7448-03-5 CAS 5800 ChemSpider 53477900 PubChem-compound 1.0 SMILES CCCCCCCCCCCCCCCC(O)=O SMILES CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C CO2 Carbon dioxide 43.98983 C01164 KEGG Compound 1.0 2.0 Coenzyme A SMILES O=O 1.0 1.0 CHEBI:27910 ChEBI HMDB06271 HMDB 1.0 BiologicalState9 BiologicalState8 BiologicalState5 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 53477909 PubChem-compound SMILES OC=O 14265-44-2 CAS Isopentenyl-diphosphate Delta-isomerase 1 Squalene 58-64-0 CAS P14324 UniProt C01054 KEGG Compound Farnesyl pyrophosphate synthase Geranylgeranyl pyrophosphate synthase SMILES C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O C27H44O Desmosterol 384.3392 960 ChemSpider Mevalonate kinase 1.0 1.0 1.0 985 PubChem-compound 644102 PubChem-compound 444493 PubChem-compound C01189 KEGG 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 1.0 ACETYL-COA BioCyc 1.0 H2O Water 18.010565 22212495 PubChem-compound 1.0 Lanosterin Isopentenyl-diphosphate Delta-isomerase 1 HMDB00961 HMDB 977 PubChem-compound C27H44O Vitamin D3 384.3392 C05437 KEGG Compound C05439 KEGG Compound 627 ChemSpider 1.0 Desmosterol 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase 8-Dehydrocholesterol Q13907 UniProt P48449 UniProt Isopentenyl pyrophosphate 17215925 ChemSpider 4.0 9058792 ChemSpider CPD-8621 BioCyc C05443 KEGG Compound CPD-4141 BioCyc C27H44O 8-Dehydrocholesterol 384.3392 80-99-9 CAS 5a-Cholesta-7,24-dien-3b-ol 4a-Methylzymosterol-4-carboxylic acid C27H44O Zymosterol intermediate 2 384.3392 SMILES O Reaction995 true 7-Dehydrocholesterol → Vitamin D3 LEFT_TO_RIGHT Reaction996 true 7-Dehydrocholesterol → 8-Dehydrocholesterol LEFT_TO_RIGHT 1.3.1.72 false 1.3.1.72 Desmosterol + NADPH ↔ Cholesterol + NADP REVERSIBLE C6H12O4 Mevalonic acid 148.07356 1.3.1.72 false 1.3.1.72 7-Dehydrodesmosterol + NADPH ↔ 7-Dehydrocholesterol + NADP REVERSIBLE SQUALENE BioCyc Fatty acid Delta(24)-sterol reductase Phosphomevalonate kinase SMILES CC(C)CCC[C@@H](C)[C@H]1CCC2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C Acetyl-CoA acetyltransferase, cytosolic 92746 PubChem-compound Diphosphomevalonate decarboxylase 1.0 Desmosterol 393270 ChemSpider 6816 PubChem-compound C27H46O Cholesterol 386.35486 ADP BioCyc 7-DEHYDRO-CHOLESTEROL BioCyc ReactionCatalysis258 ACTIVATION Dimethylallylpyrophosphate 1.0 53-59-8 CAS Lysosome 1553-55-5 CAS 358-72-5 CAS C05107 KEGG Compound 1.0 C05109 KEGG Compound C05108 KEGG Compound C05103 KEGG Compound SMILES [H][C@@](C)(CCCC(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 [H][C@@](C)(CCC=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 Cholesterol Ester 79-63-0 CAS 1.0 (S)-5-Diphosphomevalonic acid 3.0 278 ChemSpider 91952 ChemSpider 274 ChemSpider CHEBI:505093 ChEBI 3-keto-steroid reductase CPD-641 BioCyc O4P Phosphate 94.95342 3-hydroxy-3-methylglutaryl-coenzyme A reductase Adenosine triphosphate 7-Dehydrocholesterol 25994967 ChemSpider C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 C27H44O 7-Dehydrocholesterol 384.3392 Acetyl-CoA SubPathwayOutput Reaction957 false Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate LEFT_TO_RIGHT NADPH BioCyc 449 PubChem-compound Mevalonic acid-5P 50990081 PubChem-compound C5H12O7P2 Isopentenyl pyrophosphate 246.00583 1.0 CPD-6641 BioCyc SMILES [O-]P([O-])([O-])=O 124-38-9 CAS CHEBI:16608 ChEBI GO:0005764 GENE ONTOLOGY 1.0 1.0 Oxygen 1.14.13.72 false 1.14.13.72 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + 3 NADPH + 3 Oxygen → 4a-Methylzymosterol-4-carboxylic acid + 3 NADP + 4 Water LEFT_TO_RIGHT 1.1.1.170 false 1.1.1.170 4a-Methylzymosterol-4-carboxylic acid + NADP → 3-Keto-4-methylzymosterol + Carbon dioxide + NADPH LEFT_TO_RIGHT 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 1.3.1.72 false 1.3.1.72 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADP LEFT_TO_RIGHT 1.3.1.72 false 1.3.1.72 Lanosterin + NADPH ↔ 24,25-Dihydrolanosterol + NADP REVERSIBLE CHEBI:15899 ChEBI 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 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 [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC=C2C[C@@H](O)CC[C@]12C 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 O76062 UniProt Zymosterol intermediate 2 393471 ChemSpider Reaction739 false Geranyl-PP + Isopentenyl pyrophosphate → Farnesyl pyrophosphate + Pyrophosphate LEFT_TO_RIGHT 53-57-6 CAS CPD-8606 BioCyc 1.0 5a-Cholesta-7,24-dien-3b-ol 1.3.1.72 false 1.3.1.72 5a-Cholesta-7,24-dien-3b-ol + NADPH ↔ Lathosterol + NADP REVERSIBLE Lysosomal acid lipase/cholesteryl ester hydrolase Reaction978 false 5a-Cholesta-7,24-dien-3b-ol → 7-Dehydrodesmosterol LEFT_TO_RIGHT 1.0 1.1.1.34 false 1.1.1.34 3-Hydroxy-3-methylglutaryl-CoA + NADPH → Coenzyme A + Mevalonic acid + NADP LEFT_TO_RIGHT 2.7.1.36 false 2.7.1.36 Adenosine triphosphate + Mevalonic acid → Adenosine diphosphate + Mevalonic acid-5P LEFT_TO_RIGHT SMILES O=C=O C45H80O2 Cholesterol Ester 652.61584 1.0 C16H32O2 Fatty acid 256.24023 O7P2 Pyrophosphate 173.91193 C25H40N7O18P3S Acetoacetyl-CoA 851.13635 4-METHYL-824-CHOLESTADIENOL BioCyc Acetoacetyl-CoA SubPathwayOutput 5957 PubChem-compound 1.0 439418 PubChem-compound Reaction971 true 4a-Methylzymosterol → Zymosterol intermediate 2 LEFT_TO_RIGHT 1.3.1.72 false 1.3.1.72 NADPH + Zymosterol intermediate 2 → 5a-Cholest-8-en-3b-ol + NADP LEFT_TO_RIGHT C30H50 Squalene 410.39127 Reaction970 false 3-Keto-4-methylzymosterol + NADPH → 4a-Methylzymosterol + NADP LEFT_TO_RIGHT Cholesterol SubPathwayInput 1.0 7-Dehydrocholesterol Q15126 UniProt 1.0 Q15125 UniProt 1.0 VITAMIN_D_%7B3%7D BioCyc CHEBI:17813 ChEBI 5.3.3.5 false 5.3.3.5 7-Dehydrocholesterol + NADPH → Cholesterol + NADP LEFT_TO_RIGHT Reaction989 false 7-Dehydrodesmosterol → Desmosterol LEFT_TO_RIGHT CHEBI:15756 ChEBI 1.0 (S)-2,3-Epoxysqualene 439400 PubChem-compound Cholesterol Ester C10H15N5O10P2 Adenosine diphosphate 427.02942 HMDB01090 HMDB GO:0005737 GENE ONTOLOGY 5a-Cholest-8-en-3b-ol 11025495 PubChem-compound C6H13O7P Mevalonic acid-5P 228.03989 79-62-9 CAS 1.14.13.132 false 1.14.13.132 NADPH + Oxygen + Squalene → (S)-2,3-Epoxysqualene + NADP + Water LEFT_TO_RIGHT Lathosterol Coenzyme A 5.4.99.7 false 5.4.99.7 (S)-2,3-Epoxysqualene → Lanosterin LEFT_TO_RIGHT 1.14.21.6 false 1.14.21.6 Lathosterol + NADPH + Oxygen ↔ 7-Dehydrocholesterol + NADP + 2 Water REVERSIBLE 2.5.1.21 false 2.5.1.21 2 Farnesyl pyrophosphate + NADPH → NADP + 2 Pyrophosphate + Squalene LEFT_TO_RIGHT 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 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 10883523 PubChem-compound C01802 KEGG Compound P35610 UniProt Endoplasmic Reticulum Endoplasmic Reticulum Membrane CPD-8587 BioCyc Geranylgeranyl pyrophosphate synthase HMDB01188 HMDB CHEBI:15441 ChEBI 7-Dehydrodesmosterol 2.0 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 Phosphomevalonate kinase Delta(14)-sterol reductase 1.0 1.0 1.0 Q15738 UniProt Lanosterol synthase 4a-Methylzymosterol 14000-31-8 CAS ReactionCatalysis543 ACTIVATION CHEBI:17759 ChEBI 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 C21H36N7O16P3S Coenzyme A 767.11523 439423 PubChem-compound 18971002 PubChem-compound Cytoplasm Q14534 UniProt 5.3.3.5 false 5.3.3.5 Lathosterol → 5a-Cholest-8-en-3b-ol LEFT_TO_RIGHT Cell 5.3.3.5 false 5.3.3.5 Zymosterol intermediate 2 → 5a-Cholesta-7,24-dien-3b-ol LEFT_TO_RIGHT 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol Tryptophan Metabolism SubPathway ACETOACETYL-COA BioCyc 83724 ChemSpider Valine, Leucine and Isoleucine Degradation SubPathway 1.0 ReactionCatalysis573 ACTIVATION Pyruvate Metabolism SubPathway CHEBI:15422 ChEBI Butyrate Metabolism SubPathway ReactionCatalysis571 ACTIVATION Bile Acid Biosynthesis SubPathway ReactionCatalysis572 ACTIVATION Steroidogenesis SubPathway 6557 ChemSpider Fatty acid Metabolism SubPathway ReactionCatalysis570 ACTIVATION Pyruvate Metabolism SubPathway 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 1.0 HMDB01286 HMDB C27H44N7O20P3S 3-Hydroxy-3-methylglutaryl-CoA 911.1575 CHEBI:25351 ChEBI 23724604 PubChem-compound O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 439214 PubChem-compound 439577 PubChem-compound 440560 PubChem-compound GO:0005789 GENE ONTOLOGY 1.0 Isopentenyl pyrophosphate ReactionCatalysis568 ACTIVATION GO:0005783 GENE ONTOLOGY ReactionCatalysis569 ACTIVATION ReactionCatalysis566 ACTIVATION ReactionCatalysis567 ACTIVATION 439218 PubChem-compound ReactionCatalysis564 ACTIVATION CHEBI:16521 ChEBI ReactionCatalysis565 ACTIVATION Water HMDB02027 HMDB 391478 ChemSpider 1.0 CHEBI:17737 ChEBI CHEBI:16526 ChEBI Farnesyl pyrophosphate synthase HMDB01170 HMDB O95749 UniProt C29H46O3 4a-Methylzymosterol-4-carboxylic acid 442.3447 1.0 440558 PubChem-compound 73566-35-5 CAS CHEBI:16761 ChEBI Geranylgeranyl pyrophosphate synthase 7782-44-7 CAS 1.0 246983 PubChem-compound 440670 PubChem-compound 1.0 GO:0005777 GENE ONTOLOGY Dimethylallylpyrophosphate ReactionCatalysis555 ACTIVATION 1.0 Mevalonate kinase ReactionCatalysis556 ACTIVATION 9606 TAXONOMY ReactionCatalysis597 ACTIVATION PW000145 PathWhiz Farnesyl pyrophosphate C01724 KEGG Compound PW000023 PathWhiz ReactionCatalysis595 ACTIVATION ReactionCatalysis596 ACTIVATION 358-71-4 CAS HMDB06839 HMDB HMDB06838 HMDB 392413 ChemSpider (S)-5-Diphosphomevalonic acid C27H46O Lathosterol 386.35486 1715-86-2 CAS 1.0 1.0 PW000141 PathWhiz Q03426 UniProt C00751 KEGG Compound HMDB01023 HMDB CPD-4186 BioCyc SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O HMDB02111 HMDB SMP00060 SMPDB CHEBI:30751 ChEBI 128-33-6 CAS 3-Hydroxy-3-methylglutaryl-CoA 1420-36-6 CAS SMP00063 SMPDB CHEBI:15377 ChEBI HMDB00067 HMDB CHEBI:17436 ChEBI CHEBI:15379 ChEBI ReactionCatalysis584 ACTIVATION PW000014 PathWhiz 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 5886 PubChem-compound HMDB06842 HMDB HMDB06841 HMDB 1.0 1.0 Phosphate HMDB06840 HMDB 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 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 9200676 ChemSpider 3.0 SMILES [H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3 SMP00073 SMPDB Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating 280 PubChem-compound 1.0 ReactionCatalysis579 ACTIVATION 2.3.1.9 false 2.3.1.9 2 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE ReactionCatalysis578 ACTIVATION Carbon dioxide 1.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase ReactionCatalysis257 ACTIVATION ReactionCatalysis254 ACTIVATION 30776536 ChemSpider CHEBI:15467 ChEBI CHEBI:15345 ChEBI 1195 PubChem-compound ReactionCatalysis255 ACTIVATION O75845 UniProt CHEBI:17407 ChEBI Methylsterol monooxygenase 1 C00418 KEGG Compound 1.0 566-97-2 CAS 389460 ChemSpider HMDB01120 HMDB HMDB00032 HMDB HMDB01484 HMDB 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 20036827 ChemSpider 5.3.3.2 false 5.3.3.2 Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate REVERSIBLE ReactionCatalysis249 ACTIVATION NADP ReactionCatalysis248 ACTIVATION HMDB01377 HMDB CHEBI:1307929 ChEBI 1061 PubChem-compound 1.0 129846 PubChem-compound Q16850 UniProt 651-54-7 CAS 64284-64-6 CAS Formic acid SMILES CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CHEBI:15351 ChEBI HMDB01251 HMDB HMDB01375 HMDB C15915 KEGG Compound CHEBI:283119 ChEBI Squalene synthase 85-61-0 CAS 313-04-2 CAS 67-97-0 CAS 2.7.4.2 false 2.7.4.2 Adenosine triphosphate + Mevalonic acid-5P → (S)-5-Diphosphomevalonic acid + Adenosine diphosphate LEFT_TO_RIGHT 11975273 PubChem-compound