4321 3-Hydroxy-3-methylglutaryl-CoA 3-Hydroxy-3-methylglutaryl-CoA (C27H44N7O20P3S) is an endogenous compound that exists as a solid at room temperature. 3-Hydroxy-3-methylglutaryl-CoA belongs to the fatty acyl thioesters, a subclass of fatty acyls within the organic compounds. With an average molecular weight of 911.66 g/mol, 3-Hydroxy-3-methylglutaryl-CoA is a heavy molecule. Biologically, the compound serves as a human metabolite and has been detected in the intestine, fibroblasts, and the adrenal gland. It is formed when acetoacetyl-CoA condenses with Acetyl-CoA via a reaction catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway, also known as the mevalonate-dependent (MAD) route. HMG-CoA reductase catalyzes the rate-limiting step in this pathway. Statins are cholesterol-lowering drugs that inhibit HMG-CoA reductase to reduce cholesterol synthesis in peripheral tissues and the liver. Additionally, androgen increases the transcription of the HMG-CoA-reductase gene to stimulate lipogenesis in human prostate cancer cells. This compound is also found in electrical and electronic equipment antennas. 1553-55-5 439218 C27H44N7O20P3S White powder. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure. Not listed by IARC. This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. 2014-08-29T06:10:46Z 2026-04-05T14:25:29Z 3-hydroxy-3-methylglutaryl-CoA C00356 15467 3-HYDROXY-3-METHYL-GLUTARYL-COA HMG true 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 C27H44N7O20P3S 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 911.659 911.157467109 Endogenous Solid HMDB01375 388357 Williamson I P; Rodwell V W Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography. Journal of lipid research (1981), 22(1), 184-7. 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