Showing metabocard for Valerylcarnitine (BMDB0013128)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:39:06 UTC
Update Date2020-06-04 19:49:47 UTC
BMDB IDBMDB0013128
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002e-3970000000-cc02ad11bb556d164db7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f77-4900000000-d82ced3e04580715d2b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9500000000-7d159481020574a579a0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified0.064 +/- 0.018 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified0.09 +/- 0.03 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected and Quantified0.03-0.06 uMNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified0.17 +/- 0.04 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified4 +/- 2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.0 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.046 +/- 0.011 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.026 +/- * uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.03 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified4 +/- 2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.27 +/- 0.09 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.09 +/- 0.04 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition		 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8332830
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10157322
PDB IDNot Available
ChEBI IDNot Available
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.