1.0 2011-09-21 00:16:21 UTC 2015-07-21 06:57:16 UTC FDB022587 3-Hydroxy-3-methylglutaryl-CoA 3-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 A 3-hydroxy-3-methyl-Glutaryl-CoA 3-hydroxy-3-methyl-Glutaryl-Coenzyme A 3-hydroxy-3-methylglutaryl-CoA 3-Hydroxy-3-methylglutaryl-coenzyme A HMG-CoA HMG-Coenzyme A Hydroxymethylglutaroyl coenzyme A Hydroxymethylglutaryl-CoA Hydroxymethylglutaryl-Coenzyme A S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A S-(Hydrogen 3-hydroxy-3-methylpentanedioate S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A S-(Hydrogen 3-hydroxy-3-methylpentanedioic acid C27H44N7O20P3S 911.659 911.157467109 (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 acid 1553-55-5 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 InChI=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/s1 CABVTRNMFUVUDM-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 CoAs Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl thioesters Aromatic heteropolycyclic compounds (R)-3-hydroxyacyl CoAs (S)-3-hydroxyacyl CoAs 2,3,4-saturated fatty acyl CoAs 6-aminopurines Amino acids Aminopyrimidines and derivatives Azacyclic compounds Beta amino acids and derivatives Carbonyl compounds Carbothioic S-esters Carboxylic acids Coenzyme A and derivatives Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Monoalkyl phosphates Monocarboxylic acids and derivatives Monosaccharide phosphates N-acyl amines N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Tertiary alcohols Tetrahydrofurans Thioesters 6-aminopurine Alcohol Alkyl phosphate Amine Amino acid Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Beta amino acid or derivatives Carbonyl group Carbothioic s-ester Carboxamide group Carboxylic acid Carboxylic acid derivative Coenzyme a or derivatives Fatty amide Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monocarboxylic acid or derivatives Monosaccharide Monosaccharide phosphate N-acyl-amine N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Pyrimidine Ribonucleoside 3'-phosphate Secondary alcohol Secondary carboxylic acid amide Sulfenyl compound Tertiary alcohol Tetrahydrofuran Thiocarboxylic acid ester Thiocarboxylic acid or derivatives Solid logp -0.53 ALOGPS logs -2.35 ALOGPS solubility 4.10e+00 g/l ALOGPS logp -7.5 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 5 ChemAxon iupac (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 ChemAxon average_mass 911.659 ChemAxon mono_mass 911.157467109 ChemAxon 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 ChemAxon formula C27H44N7O20P3S ChemAxon inchi InChI=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/s1 ChemAxon inchikey CABVTRNMFUVUDM-MIGRVSMKSA-N ChemAxon polar_surface_area 421.16 ChemAxon refractivity 193.7 ChemAxon polarizability 81.01 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 20 ChemAxon donor_count 11 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon Butyrate Metabolism SMP00073 map00650 Ketone Body Metabolism SMP00071 map00072 Steroid Biosynthesis SMP00023 map00100 Valine, Leucine and Isoleucine Degradation SMP00032 map00280 Specdb::MsMs 71652 Specdb::MsMs 71653 Specdb::MsMs 71654 Specdb::MsMs 130359 Specdb::MsMs 130360 Specdb::MsMs 130361 HMDB01375 15467 1DQ9 #<Reference:0x000055ac3f216628> #<Reference:0x000055ac3f216470> #<Reference:0x000055ac3f2160b0> #<Reference:0x000055ac3f215ef8> #<Reference:0x000055ac3f215d40> #<Reference:0x000055ac3f215b88> #<Reference:0x000055ac3f2159d0> #<Reference:0x000055ac3f215818> #<Reference:0x000055ac3f215660> #<Reference:0x000055ac3f2154a8> #<Reference:0x000055ac3f2152f0> #<Reference:0x000055ac3f215138> #<Reference:0x000055ac3f214f80> #<Reference:0x000055ac3f214dc8> #<Reference:0x000055ac3f214c10> #<Reference:0x000055ac3f214a58> #<Reference:0x000055ac3f2148a0> 3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMGCR 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic Q8TB92 HMGCLL1 Hydroxymethylglutaryl-CoA lyase, mitochondrial P35914 HMGCL Hydroxymethylglutaryl-CoA synthase, cytoplasmic Q01581 HMGCS1 Hydroxymethylglutaryl-CoA synthase, mitochondrial P54868 HMGCS2 Methylglutaconyl-CoA hydratase, mitochondrial Q13825 AUH