Showing metabocard for Valerylcarnitine (BMDB0013128)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:39:06 UTC
Update Date2020-06-04 19:49:47 UTC
MCDB ID BMDB0013128
Secondary Accession Numbers
  • BMDB13128
Metabolite Identification
Common NameValerylcarnitine
DescriptionValerylcarnitine, also known as pentanoylcarnitine or C5-carnitine, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Valerylcarnitine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Valerylcarnitine has been found to be associated with several diseases known as short/branched chain acyl-coa dehydrogenase deficiency, pregnancy, obesity, and eosinophilic esophagitis; also valerylcarnitine has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Valeryl-L-carnitineHMDB
O-Valeroyl-L-carnitineHMDB
PentanoylcarnitineHMDB
Pentanoyl-L-carnitineHMDB
C5-CarnitineHMDB
Valeryl L-carnitineHMDB
ValerylcarnitineHMDB
Acylcarnitine C5:0HMDB
C5:0 CarnitineHMDB
Valeryl carnitineHMDB
Chemical FormulaC12H24NO4
Average Molecular Weight246.326
Monoisotopic Molecular Weight246.169984677
IUPAC Name[(2R)-3-carboxy-2-(pentanoyloxy)propyl]trimethylazanium
Traditional Name[(2R)-3-carboxy-2-(pentanoyloxy)propyl]trimethylazanium
CAS Registry Number40225-14-7
SMILES
CCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C12H23NO4/c1-5-6-7-12(16)17-10(8-11(14)15)9-13(2,3)4/h10H,5-9H2,1-4H3/p+1/t10-/m1/s1
InChI KeyVSNFQQXVMPSASB-SNVBAGLBSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Amine
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-1.5ALOGPS
logP-2.9ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity75.63 m³·mol⁻¹ChemAxon
Polarizability27.22 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002e-3970000000-cc02ad11bb556d164db72019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f77-4900000000-d82ced3e04580715d2b22019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9500000000-7d159481020574a579a02019-02-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified3.0 +/- 0.1 uM details
Detected and Quantified4.1 +/- 0.1 uM details
Detected and Quantified4.5 +/- 0.1 uM details
Detected and Quantified2.8 +/- 0.1 uM details
HMDB IDHMDB0013128
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029301
KNApSAcK IDNot Available
Chemspider ID17353685
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10157322
PDB IDNot Available
ChEBI ID85095
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
  3. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.