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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:57:13 UTC
Update Date2019-07-23 07:14:11 UTC
HMDB IDHMDB0060372
Secondary Accession Numbers
  • HMDB60372
Metabolite Identification
Common Name3-Hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA
Description3-Hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA, also known as 3-hydroxy-3-isohexeneylglutaryl-CoA, 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. Thus, 3-hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA is considered to be a fatty ester lipid molecule. 3-Hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866051
Synonyms
ValueSource
3-Hydroxy-3-isohexeneylglutaryl-CoAKegg
Chemical FormulaC32H52N7O20P3S
Average Molecular Weight979.776
Monoisotopic Molecular Weight979.220067365
IUPAC Name3-[2-({2-[(3-{[(2R)-4-({[({[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoethyl]-3-hydroxy-7-methyloct-6-enoic acid
Traditional Name3-[2-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoethyl]-3-hydroxy-7-methyloct-6-enoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCCC(O)(CC(O)=O)CC(=O)SCCN=C(O)CCN=C(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=C(N)N=CN=C12
InChI Identifier
InChI=1S/C32H52N7O20P3S/c1-18(2)6-5-8-32(47,12-21(41)42)13-22(43)63-11-10-34-20(40)7-9-35-29(46)26(45)31(3,4)15-56-62(53,54)59-61(51,52)55-14-19-25(58-60(48,49)50)24(44)30(57-19)39-17-38-23-27(33)36-16-37-28(23)39/h6,16-17,19,24-26,30,44-45,47H,5,7-15H2,1-4H3,(H,34,40)(H,35,46)(H,41,42)(H,51,52)(H,53,54)(H2,33,36,37)(H2,48,49,50)/t19-,24-,25-,26+,30-,32?/m1/s1
InChI KeyATTJZXQHBIJXLV-AWVQIHIZSA-N
Chemical Taxonomy
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
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • Monoterpenoid
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Aromatic monoterpenoid
  • Bicyclic monoterpenoid
  • 6-aminopurine
  • Medium-chain hydroxy acid
  • Imidazopyrimidine
  • Purine
  • Medium-chain fatty acid
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Hydroxy fatty acid
  • Fatty acid
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Imidolactam
  • Fatty amide
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Unsaturated fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidazole
  • Tetrahydrofuran
  • Azole
  • Tertiary alcohol
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.46 g/LALOGPS
logP-0.02ALOGPS
logP-3.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.88ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area428.14 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity218.47 m³·mol⁻¹ChemAxon
Polarizability92.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1945100207-8a3756d132cd3def1986Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0952300000-c4f2e1bc2eded7688a63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1922000000-71f7757a363d6729d178Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02cr-3811122409-f7d489dd9a0572761bf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910201001-8cd299e1877fdbfdf9feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-eca80d69f0cd184215aeSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04675
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966138
PDB IDNot Available
ChEBI ID15483
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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
Reactions
3-Hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA → 7-Methyl-3-oxo-6-octenoyl-CoA + Acetic aciddetails