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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-02 23:54:56 UTC
Update Date2017-10-31 16:15:02 UTC
HMDB IDHMDB0013129
Secondary Accession Numbers
  • HMDB13129
Metabolite Identification
Common NameGlutaconylcarnitine
DescriptionGlutaconylcarnitine is classified as a member of the acyl carnitines. Acyl carnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Glutaconylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. Glutaconylcarnitine is a fatty ester lipid molecule. Glutaconylcarnitine can be found in blood and urine. Within a cell, Glutaconylcarnitine is primarily located in the extracellular space and near the membrane.
Structure
Thumb
Synonyms
ValueSource
Glutaconyl-L-carnitineHMDB
Chemical FormulaC12H19NO6
Average Molecular Weight273.2824
Monoisotopic Molecular Weight273.121237345
IUPAC Name(3S)-3-{[(2E)-4-carboxybut-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-{[(2E)-4-carboxybut-2-enoyl]oxy}-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
OC(=O)C\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C12H19NO6/c1-13(2,3)8-9(7-11(16)17)19-12(18)6-4-5-10(14)15/h4,6,9H,5,7-8H2,1-3H3,(H-,14,15,16,17)/b6-4+/t9-/m0/s1
InChI KeyJXVUHLILXGZLFR-DNQSNQRASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Tricarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Enoate ester
  • Tetraalkylammonium salt
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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
Water Solubility0.13 g/LALOGPS
logP-1.7ALOGPS
logP-3.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.73 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity89.22 m³·mol⁻¹ChemAxon
Polarizability27.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-2add729af098ddd82694View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 +/- 0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.005-0.030 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.04 (0.01-0.06) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0725 (0.1405) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.0262 (0.005) uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021866
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481620
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.