HMG-CoA

HCID 445127

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Basic information

CAS: 1553-55-5
Standard SMILES: CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](C)(O)CC(=O)O
InChIKey: CABVTRNMFUVUDM-VRHQGPGLSA-N
Molecular formula: C27H44N7O20P3S
Average molar mass: 911.7 g/mol
Monoisotopic mass: 911.15746899

Names & identifiers

Preferred name: HMG-CoA
IUPAC: (3S)-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

HMG-CoA(S)-3-hydroxy-3-methylglutaryl-CoAhydroxymethylglutaryl-CoAHydroxymethylglutaroyl coenzyme A3-hydroxy-3-methylglutaryl-coenzyme A1553-55-5(3S)-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 acidCHEBI:15467S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A(3S)-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:70416coenzyme A, 3-hydroxy-3-methylglutaryl-

Show more names

3-Hydroxy-3-methylglutaryl-CoAKetorolac Impurity 573-Hydroxy-3-methylglutaryl-CoA sodium saltCoenzyme A, S-(hydrogen 3-hydroxy-3-methylpentanedioate)5-[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

216-301-7HMG-coenzyme A(3S)-3-hydroxy-3-methylglutaryl-CoA(S)-3-hydroxy-3-methylglutaryl-coenzyme AMevaldyl-Coenzyme A26926-09-0S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A3-hydroxy-3-methyl-glutaryl-CoA

Database identifiers

CAS: 1553-55-5、26926-09-0
PubChem CID: 445127
DTXSID: DTXSID40862689
ChEMBL: CHEMBL1794644
ChEBI: CHEBI:15467
EC Number: 216-301-7

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

Physical DescriptionSolid

Collision Cross Section · 2 items

265.4 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；261.9 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；266.2 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；267.3 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

259.35 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

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

Chemistry & industry

Pharmacology

Tissue LocationsAdrenal Gland；Fibroblasts；Intestine

Cellular LocationsCytoplasm；Endoplasmic reticulum；Extracellular；Membrane；Mitochondria；Peroxisome

Metabolite Pathways · 1 item

2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency；3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency；3-hydroxyisobutyric acid dehydrogenase deficiency；3-hydroxyisobutyric aciduria；3-Methylcrotonyl Coa Carboxylase Deficiency Type I；3-Methylglutaconic Aciduria Type I；3-Methylglutaconic Aciduria Type III；3-Methylglutaconic Aciduria Type IV；Alendronate Action Pathway；Atorvastatin Action Pathway；Total 43 pathways, visit the HMDB page for details

Applications

UsesHMG-CoA is an intermediate in the mevalonate pathway.

Suppliers9 total

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Alfa Chemistry+1-5166625404 · [email protected]

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.