Record Information
Version1.0
Created at2020-04-17 18:49:25 UTC
Updated at2020-12-07 19:11:15 UTC
CannabisDB IDCDB004909
Secondary Accession NumbersNot Available
Cannabis Compound 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. 3-Hydroxy-3-methylglutaryl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight911.66
Monoisotopic Molecular Weight911.1575
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 Number26926-09-0
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0891000250-052d51ef28faa9ab5b73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0971100000-dc16942c0a4531c8cb60Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1950000000-12dcb50a3caaf20a9aa5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o4-4901031462-49fbf273ff8df18347bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900110010-0be1f0212b5d814ea24cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-fffa063c59d4fcd54e7aSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Hydroxymethylglutaryl-CoA lyase, mitochondrialHMGCL1p36.1-p35P35914 details
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS21p13-p12P54868 details
Hydroxymethylglutaryl-CoA synthase, cytoplasmicHMGCS15p14-p13Q01581 details
3-hydroxy-3-methylglutaryl-coenzyme A reductaseHMGCR5q13.3-q14P04035 details
Methylglutaconyl-CoA hydratase, mitochondrialAUH9q22.31Q13825 details
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL16p12.1Q8TB92 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL16p12.1Q8TB92 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001375
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:
HMGCL
Uniprot ID:
P35914
Molecular weight:
34359.84
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
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:
P54868
Molecular weight:
52481.065
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS1
Uniprot ID:
Q01581
Molecular weight:
57293.105
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
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:
P04035
Molecular weight:
97475.155
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of 3-methylglutaconyl-CoA to 3-hydroxy-3-methylglutaryl-CoA. Has very low enoyl-CoA hydratase activity. Was originally identified as RNA-binding protein that binds in vitro to clustered 5'-AUUUA-3' motifs.
Gene Name:
AUH
Uniprot ID:
Q13825
Molecular weight:
35608.18
General function:
Involved in catalytic activity
Specific function:
Non-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, the products of which support energy production in nonhepatic animal tissues.
Gene Name:
HMGCLL1
Uniprot ID:
Q8TB92
Molecular weight:
36327.465