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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-02 23:32:58 UTC
Update Date2019-07-23 05:58:35 UTC
HMDB IDHMDB0013128
Secondary Accession Numbers
  • HMDB13128
Metabolite Identification
Common NameValerylcarnitine
DescriptionValerylcarnitine belongs to the class of organic compounds known as acylcarnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Valerylcarnitine is considered to be a practically insoluble (in water) and relatively neutral molecule. Valerylcarnitine is a fatty ester lipid molecule. Valerylcarnitine can be found in blood, cerebrospinal fluid (CSF), and urine. Within a cell, valerylcarnitine is primarily located in the extracellular space and near the membrane. Valerylcarnitine can be found in cow's milk.
Structure
Data?1563861515
Synonyms
ValueSource
Valeryl-L-carnitineHMDB
O-Valeroyl-L-carnitineHMDB
PentanoylcarnitineHMDB
Pentanoyl-L-carnitineHMDB
C5-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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 Solubility0.016 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002e-3970000000-cc02ad11bb556d164db7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f77-4900000000-d82ced3e04580715d2b2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9500000000-7d159481020574a579a0JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.400 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified0.14 +/- 0.06 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.040-0.260 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.600 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified0.16(0.04) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.46 uMNewborn (0-30 days old)Not SpecifiedNormal details
BloodDetected and Quantified0.14 +/- 0.04 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.310 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.013 +/- 0.006 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified0.21 +/- 0.09 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.14 +/- 0.06 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.220 (0.037-0.440) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<3.0 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected and Quantified0.9187 +/- 0.4397 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified27.300-48.200 uMNot SpecifiedNot SpecifiedIsovaleric acidemia details
BloodDetected and Quantified0.2(0.06) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.22(0.08) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified0.0845 (0.0722) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.1179 (0.0241) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.510-2.0800 uMNewborn (0-30 days old)Both2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD) details
BloodDetected and Quantified0.34 uMChildren (1-13 years old)Male2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD) details
BloodDetected and Quantified0.089 +/- 0.041 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.096 +/- 0.031 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
UrineDetected and Quantified0.6537 +/- 0.7142 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.4795 +/- 0.3669 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Isovaleric acidemia
  1. Matern D, He M, Berry SA, Rinaldo P, Whitley CB, Madsen PP, van Calcar SC, Lussky RC, Andresen BS, Wolff JA, Vockley J: Prospective diagnosis of 2-methylbutyryl-CoA dehydrogenase deficiency in the Hmong population by newborn screening using tandem mass spectrometry. Pediatrics. 2003 Jul;112(1 Pt 1):74-8. [PubMed:12837870 ]
Short/branched chain acyl-CoA dehydrogenase deficiency
  1. Sass JO, Ensenauer R, Roschinger W, Reich H, Steuerwald U, Schirrmacher O, Engel K, Haberle J, Andresen BS, Megarbane A, Lehnert W, Zschocke J: 2-Methylbutyryl-coenzyme A dehydrogenase deficiency: functional and molecular studies on a defect in isoleucine catabolism. Mol Genet Metab. 2008 Jan;93(1):30-5. doi: 10.1016/j.ymgme.2007.09.002. Epub 2007 Oct 22. [PubMed:17945527 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
  • 601665 (Obesity)
  • 243500 (Isovaleric acidemia)
  • 610006 (Short/branched chain acyl-CoA dehydrogenase deficiency)
  • 610247 (Eosinophilic esophagitis)
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. 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.