Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (BMDB0001375)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:58 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0001375
Secondary Accession Numbers
  • BMDB01375
Metabolite Identification
Common Name3-Hydroxy-3-methylglutaryl-CoA
Description3-Hydroxy-3-methylglutaryl-CoA, also known as hydroxymethylglutaroyl coenzyme A or HMG-CoA, belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration. Thus, 3-hydroxy-3-methylglutaryl-CoA is considered to be a fatty ester lipid molecule. 3-Hydroxy-3-methylglutaryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
(S)-3-Hydroxy-3-methylglutaryl-CoAChEBI
(S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
HMG-CoAChEBI
HMG-coenzyme AChEBI
Hydroxymethylglutaroyl coenzyme AChEBI
Hydroxymethylglutaryl-CoAChEBI
(3S)-3-Hydroxy-3-methylglutaryl-CoAHMDB
(S)-3-Hydroxy-3-methylglutaryl coenzyme AHMDB
3-Hydroxy-3-methylglutaryl CoAHMDB
3-Hydroxy-3-methylglutaryl coenzyme AHMDB
Hydroxymethylglutaryl CoAHMDB
Hydroxymethylglutaryl coenzyme AHMDB
beta-Hydroxy-beta-methylglutaryl CoAHMDB
beta-Hydroxy-beta-methylglutaryl-CoAHMDB
beta-Hydroxy-beta-methylglutaryl-coenzyme AHMDB
Β-hydroxy-β-methylglutaryl CoAHMDB
Β-hydroxy-β-methylglutaryl-CoAHMDB
Β-hydroxy-β-methylglutaryl-coenzyme AHMDB
3-Hydroxy-3-methylglutaryl-CoAChEBI, KEGG
Chemical FormulaC27H44N7O20P3S
Average Molecular Weight911.659
Monoisotopic Molecular Weight911.157467109
IUPAC Name(3S)-5-[(2-{3-[(2R)-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
Traditional NameHMG-CoA
CAS Registry Number1553-55-5
SMILES
C[C@](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]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
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
InChI KeyCABVTRNMFUVUDM-VRHQGPGLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(S)-3-hydroxy-3-alkylglutaryl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Fatty amide
  • Pyrimidine
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Amino acid
  • Carboxamide group
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.53ALOGPS
logP-6.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.81ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.7 m³·mol⁻¹ChemAxon
Polarizability82.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Adrenal Gland
  • Fibroblasts
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001375
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030158
KNApSAcK IDC00007270
Chemspider ID392859
KEGG Compound IDC00356
BioCyc ID3-HYDROXY-3-METHYL-GLUTARYL-COA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound445127
PDB IDNot Available
ChEBI ID15467
References
Synthesis ReferenceWilliamson 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA synthase, mitochondrial
General function:
Lipid transport and metabolism
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
Q2KIE6
Molecular weight:
56895.0
Reactions
Acetyl-CoA + Acetoacetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
Enzyme Details
2. Hydroxymethylglutaryl-CoA lyase, mitochondrial
General function:
Amino acid transport and metabolism
Specific function:
Mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis. Terminal step in leucine catabolism. Ketone bodies (beta-hydroxybutyrate, acetoacetate and acetone) are essential as an alternative source of energy to glucose, as lipid precursors and as regulators of metabolism.
Gene Name:
HMGCL
Uniprot ID:
Q29448
Molecular weight:
34168.0
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic acid + Acetyl-CoAdetails
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoAdetails
3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic aciddetails
Enzyme Details
3. 3-hydroxy-3-methylglutaryl-coenzyme A reductase
General function:
Lipid transport and metabolism
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
A7Z064
Molecular weight:
97727.0
Reactions
3-Hydroxy-3-methylglutaryl-CoA + NADPH → Mevalonic acid + NADP + Coenzyme Adetails
Enzyme Details
4. Enoyl-CoA hydratase domain-containing protein 2, mitochondrial
General function:
Not Available
Specific function:
Not Available
Gene Name:
ECHDC2
Uniprot ID:
Q2TBT3
Molecular weight:
31604.0
Reactions
3-Methylglutaconyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoAdetails