3-Hydroxy-3-methylglutaryl-CoA

HCID 91506

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Basic information

CAS: 1553-55-5
Standard SMILES: CC(O)(CC(=O)O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O
InChIKey: CABVTRNMFUVUDM-SJBCKIPMSA-N
Molecular formula: C27H44N7O20P3S
Average molar mass: 911.7 g/mol
Monoisotopic mass: 911.1574677

Overview

3-hydroxy-3-methylglutaryl-CoA is an alpha, dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid. It has a role as a Saccharomyces cerevisiae metabolite. It is a 3-hydroxy fatty acyl-CoA and an omega-carboxyacyl-CoA. It is functionally related to a glutaryl-CoA and a 3-hydroxy-3-methylglutaric acid. It is a conjugate acid of a 3-hydroxy-3-methylglutaryl-CoA(5-).

Names & identifiers

Preferred name: 3-Hydroxy-3-methylglutaryl-CoA
IUPAC: 5-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid
English name: S-(hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A
Molecular formula: C27H44N7O20P3S
Molecular weight: 911.66

Names & synonyms

3-Hydroxy-3-methylglutaryl-CoA(4-carboxy-3-hydroxy-3-methylbutanoyl)-CoACHEBI:11814(4-carboxy-3-hydroxy-3-methylbutanoyl)-coenzyme A3'-phosphoadenosine 5'-{3-[(3R)-4-{[3-({2-[(4-carboxy-3-hydroxy-3-methylbutanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}5-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid3'-phosphoadenosine 5'-(3-((3R)-4-((3-((2-((4-carboxy-3-hydroxy-3-methylbutanoyl)sulfanyl)ethyl)amino)-3-oxopropyl)amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl) dihydrogen diphosphate)5-(2-(3-(((2R)-4-((((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-2-hydroxy-3,3-dimethylbutanoyl)amino)propanoylamino)ethylsulfanyl)-3-hydroxy-3-methyl-5-oxopentanoic acidRefChem:1067952S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme AEINECS 216-301-7Coenzyme A, S-(hydrogen 3-hydroxy-3-methylpentanedioate)

Show more names

3-hydroxy-3-methylglutaryl-coenzyme AKetorolac Impurity 573-Hydroxy-3-methylglutaryl-CoA sodium salt5-[2-[3-[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]aminopropanoylamino]ethylsulfanyl]-3-hydroxy-3-methyl-5-oxo-pentanoic acid

SCHEMBL219453SCHEMBL29353902DTXSID00935181CABVTRNMFUVUDM-SJBCKIPMSA-NLMFA07050209PD131704Q27108899(4-carboxy-3-hydroxy-3-methylbutanoyl)-CoA;(4-carboxy-3-hydroxy-3-methylbutanoyl)-coenzyme A;3-hydroxy-3-methylglutaryl-coenzyme A

Database identifiers

CAS: 1553-55-5
PubChem CID: 91506
DTXSID: DTXSID00935181
ChEBI: CHEBI:11814
Nikkaji: J482.674D

Properties

Computed structural properties

XLogP: -6.6
Topological polar surface area: 446 Å²
Hydrogen bond donors: 11
Hydrogen bond acceptors: 25
Rotatable bonds: 24
Heavy atoms: 58
Formal charge: 0
Complexity: 1,610

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Fatty acyl CoAs [FA0705]

Physicochemical properties

Density: 1.87 · 1.87±0.1 g/cm3(Predicted)
pka: 1.16 · 1.16±0.50(Predicted)

Chemistry & industry

Applications

UsesHMG-CoA is an intermediate in the mevalonate pathway.

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Additional notes · 1 item

DefinitionChEBI: 3-hydroxy-3-methylglutaryl-CoA is an alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid. It has a role as a Saccharomyces cerevisiae metabolite. It is an omega-carboxyacyl-CoA and a 3-hydroxy fatty acyl-CoA. It is functionally related to a glutaryl-CoA and a 3-hydroxy-3-methylglutaric acid.