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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2010-02-22 12:06:16 UTC
Update Date2017-12-07 02:40:05 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
Thumb
Synonyms
ValueSource
a-HydroxyhexadecanoylcarnitineHMDB
a-HydroxypalmitoylcarnitineHMDB
alpha-HydroxyhexadecanoylcarnitineHMDB
alpha-HydroxypalmitoylcarnitineHMDB
Chemical FormulaC23H45NO5
Average Molecular Weight415.6071
Monoisotopic Molecular Weight415.329773555
IUPAC Name(4S)-4-[(2-hydroxyhexadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(4S)-4-[(2-hydroxyhexadecanoyl)oxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC(O)C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C
InChI Identifier
InChI=1S/C23H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20(25)23(28)29-21(24(2,3)4)18-19-22(26)27/h20-21,25H,5-19H2,1-4H3/t20?,21-/m0/s1
InChI KeyALAYOLIEZSXQPY-LBAQZLPGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical 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 Solubility5.4e-05 g/LALOGPS
logP0.86ALOGPS
logP1.49ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.66 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity138.5 m³·mol⁻¹ChemAxon
Polarizability51.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5941000000-b0319f34aab020f87950View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-7901100000-886b24348ed9b0208b50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-1319400000-68a89a529efd18a22a07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2910000000-07bf145106b7f6ac1036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4910000000-e28111f8f3c8bb2b560bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0060900000-46e188163b0c92c9599aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0192100000-606c9e0fbb8dd9eb3ee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-4490000000-058a49553e8417b2864dView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021866
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound53481693
    PDB IDNot Available
    ChEBI 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.