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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-02-22 12:06:16 UTC
Update Date2022-03-07 02:51:29 UTC
HMDB IDHMDB0013337
Secondary Accession Numbers
  • HMDB13337
Metabolite Identification
Common Name2-Hydroxyhexadecanoylcarnitine
Description2-hydroxyhexadecanoylcarnitine, also known as a-Hydroxypalmitoylcarnitine, is classified as a member of the fatty acid esters. Fatty acid esters are carboxylic ester derivatives of a fatty acid. 2-hydroxyhexadecanoylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. 2-hydroxyhexadecanoylcarnitine is a fatty ester lipid molecule. 2-hydroxyhexadecanoylcarnitine can be found in blood. Within a cell, 2-hydroxyhexadecanoylcarnitine is primarily located in the extracellular space and near the membrane.
Structure
Data?1582753110
Synonyms
ValueSource
(3S)-3-[(11Z)-Octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoic acidGenerator
(3S)-3-[(11Z)-Octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoic acidGenerator
Chemical FormulaC25H47NO4
Average Molecular Weight425.654
Monoisotopic Molecular Weight425.350508997
IUPAC Name(3S)-3-[(11Z)-octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-[(11Z)-octadec-11-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h10-11,23H,5-9,12-22H2,1-4H3/b11-10-/t23-/m0/s1
InChI KeyHOAMADDCQBUDDY-JCKUYFFHSA-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
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
logP2ALOGPS
logP2.56ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity147.4 m³·mol⁻¹ChemAxon
Polarizability52.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+222.15230932474
DeepCCS[M-H]-218.89230932474
DeepCCS[M-2H]-253.14230932474
DeepCCS[M+Na]+229.6530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-HydroxyhexadecanoylcarnitineCCCCCC\C=C/CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C3140.8Standard polar33892256
2-HydroxyhexadecanoylcarnitineCCCCCC\C=C/CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2620.5Standard non polar33892256
2-HydroxyhexadecanoylcarnitineCCCCCC\C=C/CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2889.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyhexadecanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyhexadecanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyhexadecanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 10V, Positive-QTOFsplash10-057i-2226900000-f147392e4965ea75d0bc2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 20V, Positive-QTOFsplash10-0006-3930000000-88ead31bcec3fbf148922018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 40V, Positive-QTOFsplash10-006x-7970000000-f8339eb9ecb2414c21292018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 10V, Positive-QTOFsplash10-004i-0000900000-c76c8c1a67e6b24de5c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 20V, Positive-QTOFsplash10-002r-9000500000-4902a8769b2895518a152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyhexadecanoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected and Quantified0.26 +/- 0.14 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.24 +/- 0.1 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029400
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481699
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.