Showing metabocard for 2-Methylbutyroylcarnitine (BMDB0000378)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:37 UTC
Update Date2020-06-04 19:49:46 UTC
BMDB IDBMDB0000378
Secondary Accession Numbers
  • BMDB00378
Metabolite Identification
Common Name2-Methylbutyroylcarnitine
Description2-Methylbutyroylcarnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, 2-methylbutyroylcarnitine is considered to be a fatty ester lipid molecule. 2-Methylbutyroylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoateChEBI
3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoic acidGenerator
(2-Methylbutyryl)carnitineHMDB
L-2-Methylbutyrate (3-carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner saltHMDB
Methylbutyroyl-carnitineHMDB
Chemical FormulaC12H23NO4
Average Molecular Weight245.3153
Monoisotopic Molecular Weight245.162708229
IUPAC Name3-[(2-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name2-methylbutyroylcarnitine
CAS Registry Number31023-25-3
SMILES
CCC(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C12H23NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3
InChI KeyIHCPDBBYTYJYIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Branched fatty acid
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-2ALOGPS
logP-2.8ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity86.44 m³·mol⁻¹ChemAxon
Polarizability26.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000378
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021996
KNApSAcK IDNot Available
Chemspider ID4932320
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5367
PubChem Compound6426901
PDB IDNot Available
ChEBI ID73026
References
Synthesis ReferenceNakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko. Synthesis of acylcarnitines for differential diagnosis of metabolic disorders. Nippon Iyo Masu Supekutoru Gakkai Koenshu (1993), 18 129-32.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  2. 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.