1.02011-09-21 00:16:21 UTC2015-07-21 06:57:16 UTCFDB0225873-Hydroxy-3-methylglutaryl-CoA3-hydroxy-3-methylglutaryl CoA (HMG-CoA) is formed when Acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes. (PMID: 14689582) [HMDB](S)-3-hydroxy-3-methylglutaryl-CoA(S)-3-hydroxy-3-methylglutaryl-Coenzyme A3-hydroxy-3-methyl-Glutaryl-CoA3-hydroxy-3-methyl-Glutaryl-Coenzyme A3-hydroxy-3-methylglutaryl-CoA3-Hydroxy-3-methylglutaryl-coenzyme AHMG-CoAHMG-Coenzyme AHydroxymethylglutaroyl coenzyme AHydroxymethylglutaryl-CoAHydroxymethylglutaryl-Coenzyme AS-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme AS-(Hydrogen 3-hydroxy-3-methylpentanedioateS-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme AS-(Hydrogen 3-hydroxy-3-methylpentanedioic acidC27H44N7O20P3S911.659911.157467109(3S)-5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-hydroxy-3-methyl-5-oxopentanoic acid(3S)-5-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-hydroxy-3-methyl-5-oxopentanoic acid1553-55-5C[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=C2NInChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21?,25-,27+/m1/s1CABVTRNMFUVUDM-MIGRVSMKSA-N belongs to the class of organic compounds known as 3-hydroxy-3-alkylglutaryl coas. These are alpha, omega dicarboxyacyl-CoA that result from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-alkylglutaric acid.3-hydroxy-3-alkylglutaryl CoAsOrganic compoundsLipids and lipid-like moleculesFatty AcylsFatty acyl thioestersAromatic heteropolycyclic compounds(R)-3-hydroxyacyl CoAs(S)-3-hydroxyacyl CoAs2,3,4-saturated fatty acyl CoAs6-aminopurinesAmino acidsAminopyrimidines and derivativesAzacyclic compoundsBeta amino acids and derivativesCarbonyl compoundsCarbothioic S-estersCarboxylic acidsCoenzyme A and derivativesGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesImidolactamsMonoalkyl phosphatesMonocarboxylic acids and derivativesMonosaccharide phosphatesN-acyl aminesN-substituted imidazolesOrganic oxidesOrganic pyrophosphatesOrganopnictogen compoundsOxacyclic compoundsPentose phosphatesPrimary aminesPurine ribonucleoside diphosphatesRibonucleoside 3'-phosphatesSecondary alcoholsSecondary carboxylic acid amidesSulfenyl compoundsTertiary alcoholsTetrahydrofuransThioesters6-aminopurineAlcoholAlkyl phosphateAmineAmino acidAmino acid or derivativesAminopyrimidineAromatic heteropolycyclic compoundAzacycleAzoleBeta amino acid or derivativesCarbonyl groupCarbothioic s-esterCarboxamide groupCarboxylic acidCarboxylic acid derivativeCoenzyme a or derivativesFatty amideGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeImidazoleImidazopyrimidineImidolactamMonoalkyl phosphateMonocarboxylic acid or derivativesMonosaccharideMonosaccharide phosphateN-acyl-amineN-glycosyl compoundN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic pyrophosphateOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOrganosulfur compoundOxacyclePentose monosaccharidePentose phosphatePentose-5-phosphatePhosphoric acid esterPrimary aminePurinePurine ribonucleoside 3',5'-bisphosphatePurine ribonucleoside bisphosphatePurine ribonucleoside diphosphatePyrimidineRibonucleoside 3'-phosphateSecondary alcoholSecondary carboxylic acid amideSulfenyl compoundTertiary alcoholTetrahydrofuranThiocarboxylic acid esterThiocarboxylic acid or derivativesSolidlogp-0.53logs-2.35solubility4.10e+00 g/llogp-7.5pka_strongest_acidic0.83pka_strongest_basic5iupac(3S)-5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-hydroxy-3-methyl-5-oxopentanoic acidaverage_mass911.659mono_mass911.157467109smilesC[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=C2NformulaC27H44N7O20P3SinchiInChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21?,25-,27+/m1/s1inchikeyCABVTRNMFUVUDM-MIGRVSMKSA-Npolar_surface_area421.16refractivity193.7polarizability81.01rotatable_bond_count24acceptor_count20donor_count11physiological_charge-5formal_charge0Butyrate MetabolismSMP00073map00650Ketone Body MetabolismSMP00071map00072Steroid BiosynthesisSMP00023map00100Valine, Leucine and Isoleucine DegradationSMP00032map00280Specdb::MsMs71652Specdb::MsMs71653Specdb::MsMs71654Specdb::MsMs130359Specdb::MsMs130360Specdb::MsMs130361HMDB01375154671DQ9#<Reference:0x0000555675b2e5c8>#<Reference:0x0000555675b2e398>#<Reference:0x0000555675b2e190>#<Reference:0x0000555675b2df60>#<Reference:0x0000555675b2dd58>#<Reference:0x0000555675b2db50>#<Reference:0x0000555675b2d8f8>#<Reference:0x0000555675b2d6a0>#<Reference:0x0000555675b2d3f8>#<Reference:0x0000555675b2d128>#<Reference:0x0000555675b2cf20>#<Reference:0x0000555675b2ccf0>#<Reference:0x0000555675b2ca48>#<Reference:0x0000555675b2c840>#<Reference:0x0000555675b2c638>#<Reference:0x0000555675b2c3e0>#<Reference:0x0000555675b2c1d8>3-hydroxy-3-methylglutaryl-coenzyme A reductaseP04035HMGCR3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicQ8TB92HMGCLL1Hydroxymethylglutaryl-CoA lyase, mitochondrialP35914HMGCLHydroxymethylglutaryl-CoA synthase, cytoplasmicQ01581HMGCS1Hydroxymethylglutaryl-CoA synthase, mitochondrialP54868HMGCS2Methylglutaconyl-CoA hydratase, mitochondrialQ13825AUH