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388357 ChemSpider 6022 PubChem-compound PW002485 PathWhiz Farnesyl pyrophosphate C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc 388353 ChemSpider 2.5.1.-,2.5.1.1, 2.5.1.29, 2.5.1.10 false 2.5.1.-,2.5.1.1, 2.5.1.29, 2.5.1.10 Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Geranylgeranyl-PP + Pyrophosphate LEFT_TO_RIGHT 6699-20-3 CAS 2.5.1.- false 2.5.1.- Farnesyl pyrophosphate + 3 Isopentenyl pyrophosphate → All-trans-hexaprenyl diphosphate + 3 Pyrophosphate LEFT_TO_RIGHT 2.5.1.87 false 2.5.1.87 Farnesyl pyrophosphate + 13 Isopentenyl pyrophosphate → di-trans, poly-cis-polyprenyl diphosphate (C80) + 13 Pyrophosphate LEFT_TO_RIGHT P08524 UniProt C00448 KEGG Compound PW000054 PathWhiz ReactionCatalysis6580 ACTIVATION ATP BioCyc PW000051 PathWhiz 559142 ChemSpider 2.0 Unknown Mevalonic acid SubPathwayInteraction3768 SubPathway3768Reaction SubPathwayReaction SubPathwayInteraction3769 SubPathwayReaction SubPathway3769Reaction SubPathwayInteraction3766 SubPathway3766Reaction SubPathwayReaction 1.0 SubPathwayInteraction3767 SubPathway3767Reaction SubPathwayReaction 5742 ChemSpider PW000163 PathWhiz C00332 KEGG Compound CHEBI:16474 ChEBI SubPathwayInteraction3770 SubPathway3770Reaction SubPathwayReaction Carbon dioxide SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 GERANYLGERANYL-PP BioCyc HMDB0001090 HMDB C00341 KEGG Compound CHEBI:17211 ChEBI 445713 PubChem-compound SubPathwayInteraction3771 SubPathway3771Reaction SubPathwayReaction 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 PPI BioCyc 1.0 HMDB0004486 HMDB 1.0 C00353 KEGG Compound C00356 KEGG Compound C00235 KEGG Compound CHEBI:16057 ChEBI 2.3.1.9 false 2.3.1.9 2 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE C10H20O7P2 Geranyl-PP 314.06842 C00009 KEGG Compound C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider C00006 KEGG Compound C5H12O7P2 Dimethylallylpyrophosphate 246.00583 CHEBI:18009 ChEBI C00001 KEGG Compound NADP CHEBI:18361 ChEBI C00005 KEGG Compound CHEBI:18367 ChEBI Farnesyl pyrophosphate 1032 ChemSpider C00002 KEGG Compound P15496 UniProt 150-97-0 CAS Geranyl-PP C01107 KEGG Compound 1.0 763-10-0 CAS Adenosine triphosphate C00011 KEGG Compound C00010 KEGG Compound 388531 ChemSpider 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 NAD(P) BioCyc 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc Reaction6886 false Acetoacetyl-CoA + Acetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A LEFT_TO_RIGHT C6H14O10P2 (S)-5-Diphosphomevalonic acid 308.00623 445995 PubChem-compound 56-65-5 CAS C01230 KEGG Compound C00024 KEGG Compound 2.0 CPD-499 BioCyc 647 PubChem-compound P27796 UniProt 388517 ChemSpider 372-97-4 CAS HMDB0001343 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 Mevalonic acid-5P HMDB0001347 HMDB 1.0 HMDB0000250 HMDB SMILES [O-]P([O-])(=O)OP([O-])([O-])=O HMDB0001341 HMDB GERANYL-PP BioCyc Hexaprenyl pyrophosphate synthase, mitochondrial ditrans,polycis-polyprenyl diphosphate synthase RER2 dehydrodolichyl diphosphate syntase complex subunit NUS1 ditrans,polycis-polyprenyl diphosphate synthase SRT1 46926091 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 1.0 SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O Q03175 UniProt 5.3.3.2 false 5.3.3.2 Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate REVERSIBLE 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 C15H28O7P2 Farnesyl pyrophosphate 382.131 C01143 KEGG Compound 7732-18-5 CAS 436 ChemSpider SMILES CC(O)(CCO)CC(O)=O Adenosine diphosphate HMDB0001120 HMDB HMDB0001484 HMDB P35196 UniProt 4444089 ChemSpider CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 FARNESYL-PP BioCyc Pyrophosphate HMDB0001375 HMDB 962 PubChem-compound Farnesyl pyrophosphate synthase 5800 ChemSpider 1.0 3-Hydroxy-3-methylglutaryl-CoA Unknown CO2 Carbon dioxide 43.98983 1.0 Coenzyme A 1.0 ditrans,polycis-polyprenyl diphosphate synthase SRT1 Butyrate Metabolism SubPathway Hexaprenyl pyrophosphate synthase, mitochondrial dehydrodolichyl diphosphate syntase complex subunit NUS1 1.0 ditrans,polycis-polyprenyl diphosphate synthase RER2 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 14265-44-2 CAS 58-64-0 CAS 3-ketoacyl-CoA thiolase, peroxisomal 3.0 1.0 1.0 Terpenoid Backbone Biosynthesis di-trans, poly-cis-polyprenyl diphosphate (C80) C80H129O7P2 di-trans, poly-cis-polyprenyl diphosphate (C80) 1263.923 644102 PubChem-compound 4932 TAXONOMY 444493 PubChem-compound SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 22833512 PubChem-compound ACETYL-COA BioCyc H2O Water 18.010565 1.0 HMDB0001285 HMDB 2.0 627 ChemSpider HMDB0012188 HMDB SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O Isopentenyl pyrophosphate 17215925 ChemSpider Q12063 UniProt Valine, Leucine, and Isoleucine Degradation SubPathway SMILES O Pyrophosphate C6H12O4 Mevalonic acid 148.07356 SMP0002384 SMPDB HMDB0000538 HMDB 393270 ChemSpider 6816 PubChem-compound Water ADP BioCyc Dimethylallylpyrophosphate 1553-55-5 CAS Isopentenyl-diphosphate Delta-isomerase 53-59-8 CAS 358-72-5 CAS Geranylgeranyl pyrophosphate synthase 1.0 (S)-5-Diphosphomevalonic acid Fatty Acid Metabolism SubPathway 274 ChemSpider CPD-641 BioCyc O4P Phosphate 94.95342 P18900 UniProt ReactionCatalysis6922 ACTIVATION Adenosine triphosphate Tryptophan Metabolism SubPathway Pyruvate Metabolism SubPathway C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 Acetyl-CoA SubPathwayOutput Geranylgeranyl pyrophosphate synthase ReactionCatalysis6921 ACTIVATION ReactionCatalysis6920 ACTIVATION NADPH BioCyc 449 PubChem-compound Mevalonic acid-5P C5H12O7P2 Isopentenyl pyrophosphate 246.00583 HMDB0001423 HMDB SMILES [O-]P([O-])([O-])=O P24521 UniProt HMDB0000217 HMDB 124-38-9 CAS 6.0 mevalonate kinase 6.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 1.0 447277 PubChem-compound P32377 UniProt 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 CHEBI:15899 ChEBI HMDB0001429 HMDB 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 HMDB0000221 HMDB Geranylgeranyl-PP SMP0000051 SMPDB C20H36O7P2 Geranylgeranyl-PP 450.19363 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 1.0 1.0 CHEBI:48861 ChEBI 393471 ChemSpider 53-57-6 CAS 394418 ChemSpider ALL-TRANS-HEXAPRENYL-DIPHOSPHATE BioCyc 1.0 Isopentenyl-diphosphate Delta-isomerase Diphosphomevalonate decarboxylase SMILES O=C=O Farnesyl pyrophosphate synthase Phosphomevalonate kinase O7P2 Pyrophosphate 173.91193 C25H40N7O18P3S Acetoacetyl-CoA 851.13635 1.0 SMP0000060 SMPDB Acetoacetyl-CoA SubPathwayOutput 1.0 HMDB0001206 HMDB 5957 PubChem-compound 439418 PubChem-compound SMP0000063 SMPDB Isopentenyl pyrophosphate 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 439400 PubChem-compound SMP0000073 SMPDB C10H15N5O10P2 Adenosine diphosphate 427.02942 GO:0005737 GENE ONTOLOGY C6H13O7P Mevalonic acid-5P 228.03989 P12684 UniProt Coenzyme A P12683 UniProt Endoplasmic Reticulum CPD-8587 BioCyc ReactionCatalysis6859 ACTIVATION CHEBI:1146900 ChEBI ReactionCatalysis6858 ACTIVATION ReactionCatalysis6857 ACTIVATION C30H52O7P2 All-trans-hexaprenyl diphosphate 586.31885 ReactionCatalysis6856 ACTIVATION 1.0 1.0 14000-31-8 CAS P07277 UniProt CO-A BioCyc Adenosine diphosphate 5675 ChemSpider 72-89-9 CAS SMILES C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O 1.0 C21H36N7O16P3S Coenzyme A 767.11523 ReactionCatalysis6862 ACTIVATION Cytoplasm ReactionCatalysis6861 ACTIVATION ReactionCatalysis6860 ACTIVATION 1.0 ReactionCatalysis6863 ACTIVATION ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI Farnesyl pyrophosphate synthase 6557 ChemSpider 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 C27H44N7O20P3S 3-Hydroxy-3-methylglutaryl-CoA 911.1575 CHEBI:25351 ChEBI 13.0 439214 PubChem-compound 3-ketoacyl-CoA thiolase, peroxisomal All-trans-hexaprenyl diphosphate 1.0 Isopentenyl pyrophosphate 13.0 GO:0005783 GENE ONTOLOGY 439218 PubChem-compound 1.0 CHEBI:16526 ChEBI 73566-35-5 CAS CHEBI:16761 ChEBI 5280413 PubChem-compound 1.0 HMDB0000961 HMDB GO:0005777 GENE ONTOLOGY SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP([O-])(=O)OP([O-])([O-])=O ReactionCatalysis6882 ACTIVATION Dimethylallylpyrophosphate SMP0000032 SMPDB PW000023 PathWhiz 358-71-4 CAS 392413 ChemSpider (S)-5-Diphosphomevalonic acid 1.0 Diphosphomevalonate decarboxylase SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O 3-Hydroxy-3-methylglutaryl-CoA 1.0 1420-36-6 CAS CHEBI:15377 ChEBI CHEBI:17436 ChEBI Phosphomevalonate kinase Unknown PW000014 PathWhiz 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 5886 PubChem-compound 1.0 1.0 Phosphate CHEBI:16584 ChEBI 280 PubChem-compound 1.0 CHEBI:15467 ChEBI CHEBI:15345 ChEBI 1195 PubChem-compound CHEBI:17407 ChEBI CHEBI:17528 ChEBI C00418 KEGG Compound dehydrodolichyl diphosphate synthase complex mevalonate kinase 3.0 SMILES CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O 1.0 1061 PubChem-compound 1.0 HMDB0001967 HMDB SMILES CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CHEBI:15351 ChEBI 1.1.1.34 false 1.1.1.34 3-Hydroxy-3-methylglutaryl-CoA + NADPH → Coenzyme A + Mevalonic acid + NADP LEFT_TO_RIGHT 85-61-0 CAS Unknown Acetyl-CoA acetyltransferase, cytosolic Mevalonate kinase Phosphomevalonate kinase Diphosphomevalonate decarboxylase Isopentenyl- diphosphate Delta-isomerase 1 Farnesyl pyrophosphate synthase Geranylgeranyl pyrophosphate synthase Farnesyl pyrophosphate synthase Geranylgeranyl pyrophosphate synthase 3-hydroxy-3- methylglutaryl- coenzyme A reductase Geranylgeranyl pyrophosphate synthase Hexaprenyl pyrophosphate synthase, mitochondrial ditrans,polycis- polyprenyl diphosphate synthase RER2 dehydrodolichyl diphosphate syntase complex subunit NUS1 ditrans,polycis- polyprenyl diphosphate synthase SRT1 Acetoacetyl-CoA Acetyl-CoA CoA H 2 O 3-Hydroxy-3-methylglutaryl-CoA CoA Mevalonic acid ATP Mevalonic acid-5P ADP ATP ADP (S)-5-Diphosphomevalonic acid ATP ADP P i Isopentenyl pyrophosphate CO 2 Dimethylallylpyrophosphate Geranyl-PP PP i Farnesyl pyrophosphate PP i NADPH NADP CoA Isopentenyl pyrophosphate PP i Geranylgeranyl- PP Isopentenyl pyrophosphate All-trans- hexaprenyl diphosphate PP i Isopentenyl pyrophosphate di-trans, poly-cis- polyprenyl diphosphate (C80) PP i Magnesium Magnesium Magnesium Magnesium Magnesium Butyrate Metabolism Pyruvate Metabolism Valine, Leucine, and Isoleucine Degradation Tryptophan Metabolism Pyruvate Metabolism Fatty Acid Metabolism Endoplasmic Reticulum Peroxisome Peroxisome Intracellular Space Extracellular Space Endoplasmic Reticulum Outer membrane Inner membrane
388357 ChemSpider 6022 PubChem-compound PW002485 PathWhiz Farnesyl pyrophosphate C23H38N7O17P3S Acetyl-CoA 809.1258 937 ChemSpider MEVALONATE BioCyc 388353 ChemSpider 2.5.1.-,2.5.1.1, 2.5.1.29, 2.5.1.10 false 2.5.1.-,2.5.1.1, 2.5.1.29, 2.5.1.10 Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Geranylgeranyl-PP + Pyrophosphate LEFT_TO_RIGHT 6699-20-3 CAS 2.5.1.- false 2.5.1.- Farnesyl pyrophosphate + 3 Isopentenyl pyrophosphate → All-trans-hexaprenyl diphosphate + 3 Pyrophosphate LEFT_TO_RIGHT 2.5.1.87 false 2.5.1.87 Farnesyl pyrophosphate + 13 Isopentenyl pyrophosphate → di-trans, poly-cis-polyprenyl diphosphate (C80) + 13 Pyrophosphate LEFT_TO_RIGHT P08524 UniProt C00448 KEGG Compound PW000054 PathWhiz ReactionCatalysis6580 ACTIVATION ATP BioCyc PW000051 PathWhiz 559142 ChemSpider 2.0 Unknown Mevalonic acid SubPathwayInteraction3768 SubPathway3768Reaction SubPathwayReaction SubPathwayInteraction3769 SubPathwayReaction SubPathway3769Reaction SubPathwayInteraction3766 SubPathway3766Reaction SubPathwayReaction 1.0 SubPathwayInteraction3767 SubPathway3767Reaction SubPathwayReaction 5742 ChemSpider PW000163 PathWhiz C00332 KEGG Compound CHEBI:16474 ChEBI SubPathwayInteraction3770 SubPathway3770Reaction SubPathwayReaction Carbon dioxide SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 GERANYLGERANYL-PP BioCyc HMDB0001090 HMDB C00341 KEGG Compound CHEBI:17211 ChEBI 445713 PubChem-compound SubPathwayInteraction3771 SubPathway3771Reaction SubPathwayReaction 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 PPI BioCyc 1.0 HMDB0004486 HMDB 1.0 C00353 KEGG Compound C00356 KEGG Compound C00235 KEGG Compound CHEBI:16057 ChEBI 2.3.1.9 false 2.3.1.9 2 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A REVERSIBLE C10H20O7P2 Geranyl-PP 314.06842 C00009 KEGG Compound C00008 KEGG Compound C00129 KEGG Compound 1158 ChemSpider C00006 KEGG Compound C5H12O7P2 Dimethylallylpyrophosphate 246.00583 CHEBI:18009 ChEBI C00001 KEGG Compound NADP CHEBI:18361 ChEBI C00005 KEGG Compound CHEBI:18367 ChEBI Farnesyl pyrophosphate 1032 ChemSpider C00002 KEGG Compound P15496 UniProt 150-97-0 CAS Geranyl-PP C01107 KEGG Compound 1.0 763-10-0 CAS Adenosine triphosphate C00011 KEGG Compound C00010 KEGG Compound 388531 ChemSpider 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 NAD(P) BioCyc 3-HYDROXY-3-METHYL-GLUTARYL-COA BioCyc Reaction6886 false Acetoacetyl-CoA + Acetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A LEFT_TO_RIGHT C6H14O10P2 (S)-5-Diphosphomevalonic acid 308.00623 445995 PubChem-compound 56-65-5 CAS C01230 KEGG Compound C00024 KEGG Compound 2.0 CPD-499 BioCyc 647 PubChem-compound P27796 UniProt 388517 ChemSpider 372-97-4 CAS HMDB0001343 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 Mevalonic acid-5P HMDB0001347 HMDB 1.0 HMDB0000250 HMDB SMILES [O-]P([O-])(=O)OP([O-])([O-])=O HMDB0001341 HMDB GERANYL-PP BioCyc Hexaprenyl pyrophosphate synthase, mitochondrial ditrans,polycis-polyprenyl diphosphate synthase RER2 dehydrodolichyl diphosphate syntase complex subunit NUS1 ditrans,polycis-polyprenyl diphosphate synthase SRT1 46926091 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 1.0 SMILES C[C@@](O)(CCOP(O)(O)=O)CC(O)=O Q03175 UniProt 5.3.3.2 false 5.3.3.2 Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate REVERSIBLE 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 C15H28O7P2 Farnesyl pyrophosphate 382.131 C01143 KEGG Compound 7732-18-5 CAS 436 ChemSpider SMILES CC(O)(CCO)CC(O)=O Adenosine diphosphate HMDB0001120 HMDB HMDB0001484 HMDB P35196 UniProt 4444089 ChemSpider CPD-4211 BioCyc C10H16N5O13P3 Adenosine triphosphate 506.99576 FARNESYL-PP BioCyc Pyrophosphate HMDB0001375 HMDB 962 PubChem-compound Farnesyl pyrophosphate synthase 5800 ChemSpider 1.0 3-Hydroxy-3-methylglutaryl-CoA Unknown CO2 Carbon dioxide 43.98983 1.0 Coenzyme A 1.0 ditrans,polycis-polyprenyl diphosphate synthase SRT1 Butyrate Metabolism SubPathway Hexaprenyl pyrophosphate synthase, mitochondrial dehydrodolichyl diphosphate syntase complex subunit NUS1 1.0 ditrans,polycis-polyprenyl diphosphate synthase RER2 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 14265-44-2 CAS 58-64-0 CAS 3-ketoacyl-CoA thiolase, peroxisomal 3.0 1.0 1.0 Terpenoid Backbone Biosynthesis di-trans, poly-cis-polyprenyl diphosphate (C80) C80H129O7P2 di-trans, poly-cis-polyprenyl diphosphate (C80) 1263.923 644102 PubChem-compound 4932 TAXONOMY 444493 PubChem-compound SMILES CC(=C)CCO[P@](O)(=O)OP(O)(O)=O 22833512 PubChem-compound ACETYL-COA BioCyc H2O Water 18.010565 1.0 HMDB0001285 HMDB 2.0 627 ChemSpider HMDB0012188 HMDB SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O Isopentenyl pyrophosphate 17215925 ChemSpider Q12063 UniProt Valine, Leucine, and Isoleucine Degradation SubPathway SMILES O Pyrophosphate C6H12O4 Mevalonic acid 148.07356 SMP0002384 SMPDB HMDB0000538 HMDB 393270 ChemSpider 6816 PubChem-compound Water ADP BioCyc Dimethylallylpyrophosphate 1553-55-5 CAS Isopentenyl-diphosphate Delta-isomerase 53-59-8 CAS 358-72-5 CAS Geranylgeranyl pyrophosphate synthase 1.0 (S)-5-Diphosphomevalonic acid Fatty Acid Metabolism SubPathway 274 ChemSpider CPD-641 BioCyc O4P Phosphate 94.95342 P18900 UniProt ReactionCatalysis6922 ACTIVATION Adenosine triphosphate Tryptophan Metabolism SubPathway Pyruvate Metabolism SubPathway C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 Acetyl-CoA SubPathwayOutput Geranylgeranyl pyrophosphate synthase ReactionCatalysis6921 ACTIVATION ReactionCatalysis6920 ACTIVATION NADPH BioCyc 449 PubChem-compound Mevalonic acid-5P C5H12O7P2 Isopentenyl pyrophosphate 246.00583 HMDB0001423 HMDB SMILES [O-]P([O-])([O-])=O P24521 UniProt HMDB0000217 HMDB 124-38-9 CAS 6.0 mevalonate kinase 6.0 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 1.0 447277 PubChem-compound P32377 UniProt 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 CHEBI:15899 ChEBI HMDB0001429 HMDB 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 HMDB0000221 HMDB Geranylgeranyl-PP SMP0000051 SMPDB C20H36O7P2 Geranylgeranyl-PP 450.19363 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 1.0 1.0 CHEBI:48861 ChEBI 393471 ChemSpider 53-57-6 CAS 394418 ChemSpider ALL-TRANS-HEXAPRENYL-DIPHOSPHATE BioCyc 1.0 Isopentenyl-diphosphate Delta-isomerase Diphosphomevalonate decarboxylase SMILES O=C=O Farnesyl pyrophosphate synthase Phosphomevalonate kinase O7P2 Pyrophosphate 173.91193 C25H40N7O18P3S Acetoacetyl-CoA 851.13635 1.0 SMP0000060 SMPDB Acetoacetyl-CoA SubPathwayOutput 1.0 HMDB0001206 HMDB 5957 PubChem-compound 439418 PubChem-compound SMP0000063 SMPDB Isopentenyl pyrophosphate 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 439400 PubChem-compound SMP0000073 SMPDB C10H15N5O10P2 Adenosine diphosphate 427.02942 GO:0005737 GENE ONTOLOGY C6H13O7P Mevalonic acid-5P 228.03989 P12684 UniProt Coenzyme A P12683 UniProt Endoplasmic Reticulum CPD-8587 BioCyc ReactionCatalysis6859 ACTIVATION CHEBI:1146900 ChEBI ReactionCatalysis6858 ACTIVATION ReactionCatalysis6857 ACTIVATION C30H52O7P2 All-trans-hexaprenyl diphosphate 586.31885 ReactionCatalysis6856 ACTIVATION 1.0 1.0 14000-31-8 CAS P07277 UniProt CO-A BioCyc Adenosine diphosphate 5675 ChemSpider 72-89-9 CAS SMILES C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O 1.0 C21H36N7O16P3S Coenzyme A 767.11523 ReactionCatalysis6862 ACTIVATION Cytoplasm ReactionCatalysis6861 ACTIVATION ReactionCatalysis6860 ACTIVATION 1.0 ReactionCatalysis6863 ACTIVATION ACETOACETYL-COA BioCyc CHEBI:15422 ChEBI Farnesyl pyrophosphate synthase 6557 ChemSpider 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 C27H44N7O20P3S 3-Hydroxy-3-methylglutaryl-CoA 911.1575 CHEBI:25351 ChEBI 13.0 439214 PubChem-compound 3-ketoacyl-CoA thiolase, peroxisomal All-trans-hexaprenyl diphosphate 1.0 Isopentenyl pyrophosphate 13.0 GO:0005783 GENE ONTOLOGY 439218 PubChem-compound 1.0 CHEBI:16526 ChEBI 73566-35-5 CAS CHEBI:16761 ChEBI 5280413 PubChem-compound 1.0 HMDB0000961 HMDB GO:0005777 GENE ONTOLOGY SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP([O-])(=O)OP([O-])([O-])=O ReactionCatalysis6882 ACTIVATION Dimethylallylpyrophosphate SMP0000032 SMPDB PW000023 PathWhiz 358-71-4 CAS 392413 ChemSpider (S)-5-Diphosphomevalonic acid 1.0 Diphosphomevalonate decarboxylase SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O 3-Hydroxy-3-methylglutaryl-CoA 1.0 1420-36-6 CAS CHEBI:15377 ChEBI CHEBI:17436 ChEBI Phosphomevalonate kinase Unknown PW000014 PathWhiz 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 5886 PubChem-compound 1.0 1.0 Phosphate CHEBI:16584 ChEBI 280 PubChem-compound 1.0 CHEBI:15467 ChEBI CHEBI:15345 ChEBI 1195 PubChem-compound CHEBI:17407 ChEBI CHEBI:17528 ChEBI C00418 KEGG Compound dehydrodolichyl diphosphate synthase complex mevalonate kinase 3.0 SMILES CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O 1.0 1061 PubChem-compound 1.0 HMDB0001967 HMDB SMILES CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CHEBI:15351 ChEBI 1.1.1.34 false 1.1.1.34 3-Hydroxy-3-methylglutaryl-CoA + NADPH → Coenzyme A + Mevalonic acid + NADP LEFT_TO_RIGHT 85-61-0 CAS Endoplasmic Reticulum Mitochondria Unknown Unknown Unknown Unknown Unknown Unknown Unknown Unknown Unknown Unknown Unknown Unknown COQ1 RER2 NUS1 SRT1 Acetoacetyl-CoA Acetyl-CoA Coenzyme A Water 3-Hydroxy-3- methylglutaryl- CoA Coenzyme A Mevalonic acid Adenosine triphosphate Mevalonic acid-5P Adenosine diphosphate Adenosine triphosphate Adenosine diphosphate (S)-5- Diphosphomevalonic acid Adenosine triphosphate Adenosine diphosphate Phosphate Isopentenyl pyrophosphate Carbon dioxide Dimethylallylpyrophosphate Geranyl-PP Pyrophosphate Farnesyl pyrophosphate Pyrophosphate NADPH NADP Coenzyme A Isopentenyl pyrophosphate