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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-02 22:36:44 UTC
Update Date2017-12-07 02:39:16 UTC
HMDB IDHMDB0013124
Secondary Accession Numbers
  • HMDB13124
Metabolite Identification
Common NamePropenoylcarnitine
Description Propenoylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. Propenoylcarnitine is a fatty ester lipid molecule. Propenoylcarnitine can be found in Cow milk, pasteurized, vitamin A + D added, 0% fats, Cow milk, pasteurized, vitamin A + D added, 1% fats, Cow milk, pasteurized, vitamin A + D added, 2% fats, and Cow milk, pasteurized, vitamin D added, 3.25% fats. Propenoylcarnitine can be found in blood, saliva or urine. Within a cell, Propenoylcarnitine is primarily located in the extracellular space and near the membrane. This 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.
Structure
Thumb
Synonyms
ValueSource
(3S)-3-(Prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoateChEBI
(3S)-3-(Prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoic acidGenerator
Propenoyl-L-carnitineHMDB
Chemical FormulaC10H17NO4
Average Molecular Weight215.2463
Monoisotopic Molecular Weight215.115758037
IUPAC Name(3S)-3-(prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-(prop-2-enoyloxy)-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)C=C
InChI Identifier
InChI=1S/C10H17NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h5,8H,1,6-7H2,2-4H3/t8-/m0/s1
InChI KeyYUCNWOKTRWJLGY-QMMMGPOBSA-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
  • Dicarboxylic acid or derivatives
  • Acrylic acid ester
  • Quaternary ammonium salt
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Tetraalkylammonium salt
  • Acrylic acid or derivatives
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic salt
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

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 Solubility0.059 g/LALOGPS
logP-2.2ALOGPS
logP-3.5ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity77.28 m³·mol⁻¹ChemAxon
Polarizability21.91 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 (Non-derivatized) - 70eV, Positivesplash10-05fr-9000000000-75fc08c3d27feb518327View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066v-2930000000-454a580179166d0507bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-3900000000-b50c527fe3c21e151579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi0-9400000000-4054ae16ebec41595115View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4190000000-363b169cd979e9082c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nt9-6940000000-be8367f8d194c1c16d97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-81ec5a1bdf939e2a5454View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.040-0.140 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected and Quantified0.037 +/- 0.004 uMAdult (>18 years old)BothNormal
      • Zerihun T. Dame, ...
    details
    UrineDetected and Quantified0.003 (0.001-0.006) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.0253 (0.00163) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect 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 Compound53481611
    PDB IDNot Available
    ChEBI ID86076
    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.