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Showing Compound 3-Hydroxy-3-methylglutaryl-CoA (FDB022587)

Record Information
Version1.0
Creation date2011-09-21 00:16:21 UTC
Update date2015-07-21 06:57:16 UTC
Primary IDFDB022587
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxy-3-methylglutaryl-CoA
Description3-hydroxy-3-methylglutaryl CoA (HMG-CoA) is formed when Acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes. (PMID: 14689582) [HMDB]
CAS Number1553-55-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(S)-3-Hydroxy-3-methylglutaryl-CoAHMDB
(S)-3-Hydroxy-3-methylglutaryl-coenzyme AHMDB
3-Hydroxy-3-methyl-glutaryl-CoAHMDB
3-Hydroxy-3-methyl-glutaryl-coenzyme AHMDB
3-Hydroxy-3-methylglutaryl-coenzyme AHMDB
HMG-CoAHMDB
HMG-coenzyme AHMDB
Hydroxymethylglutaroyl coenzyme AHMDB
Hydroxymethylglutaryl-CoAHMDB
Hydroxymethylglutaryl-coenzyme AHMDB
S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme AHMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioateHMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme AHMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioic acidHMDB
3-Hydroxy-3-methylglutaryl-coenzyme A, (S)-isomerHMDB
3-Hydroxy-3-methylglutaryl-coenzyme A, mono(3-oxobutanoate)HMDB
(S)-3-hydroxy-3-methylglutaryl-CoAhmdb
(S)-3-hydroxy-3-methylglutaryl-Coenzyme Ahmdb
3-hydroxy-3-methyl-Glutaryl-CoAhmdb
3-hydroxy-3-methyl-Glutaryl-Coenzyme Ahmdb
3-hydroxy-3-methylglutaryl-CoAhmdb
HMG-Coenzyme Ahmdb
Hydroxymethylglutaryl-Coenzyme Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility4.1 g/LALOGPS
logP-0.53ALOGPS
logP-7.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.7 m³·mol⁻¹ChemAxon
Polarizability81.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H44N7O20P3S
IUPAC name(3S)-5-{[2-(3-{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
InChI IdentifierInChI=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-MIGRVSMKSA-N
Isomeric SMILESC[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
Average Molecular Weight911.659
Monoisotopic Molecular Weight911.157467109
Classification
Description Belongs to the class of organic compounds known as 3-hydroxy-3-alkylglutaryl coas. These are alpha, omega dicarboxyacyl-CoA that result from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-alkylglutaric acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0891000250-052d51ef28faa9ab5b732016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0971100000-dc16942c0a4531c8cb602016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1950000000-12dcb50a3caaf20a9aa52016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o4-4901031462-49fbf273ff8df18347bb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900110010-0be1f0212b5d814ea24c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-fffa063c59d4fcd54e7a2016-08-03View Spectrum
NMRNot Available
ChemSpider ID388357
ChEMBL IDNot Available
KEGG Compound IDC00356
Pubchem Compound ID439218
Pubchem Substance IDNot Available
ChEBI ID15467
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01375
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34727
KNApSAcK IDNot Available
HET ID1DQ9
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID3-hydroxy-3-methylglutaryl-CoA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxy-3-methylglutaryl-coenzyme A reductaseHMGCRP04035
Hydroxymethylglutaryl-CoA lyase, mitochondrialHMGCLP35914
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS2P54868
Hydroxymethylglutaryl-CoA synthase, cytoplasmicHMGCS1Q01581
Methylglutaconyl-CoA hydratase, mitochondrialAUHQ13825
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL1Q8TB92
Pathways
NameSMPDB LinkKEGG Link
Butyrate MetabolismSMP00073 map00650
Ketone Body MetabolismSMP00071 map00072
Steroid BiosynthesisSMP00023 map00100
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference