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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2017-12-07 01:48:40 UTC
HMDB IDHMDB0002261
Secondary Accession Numbers
  • HMDB02261
Metabolite Identification
Common Name2-Hydroxymyristic acid
Description2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677 ).
Structure
Thumb
Synonyms
ValueSource
alpha-Hydroxy-N-tetradecylic acidChEBI
alpha-Hydroxymyristic acidChEBI
a-Hydroxy-N-tetradecylateGenerator
a-Hydroxy-N-tetradecylic acidGenerator
alpha-Hydroxy-N-tetradecylateGenerator
α-hydroxy-N-tetradecylateGenerator
α-hydroxy-N-tetradecylic acidGenerator
2-HydroxymyristateGenerator
a-HydroxymyristateGenerator
a-Hydroxymyristic acidGenerator
alpha-HydroxymyristateGenerator
α-hydroxymyristateGenerator
α-hydroxymyristic acidGenerator
2-Hydroxy-myristic-acidHMDB
2-HydroxytetradecanoateHMDB
2-Hydroxytetradecanoic acidHMDB
DL-a-HydroxymyristateHMDB
DL-a-Hydroxymyristic acidHMDB
DL-alpha-HydroxymyristateHMDB
DL-alpha-Hydroxymyristic acidHMDB
Chemical FormulaC14H28O3
Average Molecular Weight244.3703
Monoisotopic Molecular Weight244.203844762
IUPAC Name2-hydroxytetradecanoic acid
Traditional Name2-hydroxymyristic acid
CAS Registry Number2507-55-3
SMILES
CCCCCCCCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)
InChI KeyJYZJYKOZGGEXSX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.019 g/LALOGPS
logP4.71ALOGPS
logP4.5ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity69.37 m³·mol⁻¹ChemAxon
Polarizability30.7 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, Positivesplash10-002g-9700000000-8493ca6732d2b7ebf6b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9242000000-206629d5379d5a4a3a86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0390000000-fa16fe269769b95e9682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ot-3930000000-58ff17a1c4711e739574View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-1ceac1323899f5bc74f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-7ba586681c0bf7368a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-0960000000-5b0f96b6ff1eb7d2407cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-6900000000-a272f854b23f304deab7View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
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 IDFDB022931
KNApSAcK IDNot Available
Chemspider ID1508
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6579
PubChem Compound1563
PDB IDNot Available
ChEBI ID59270
References
Synthesis ReferenceSkipski, Vladimir P.; Arfin, Stuart M.; Rapport, Maurice M. Paper chromatography of saturated, unsaturated, and hydroxy fatty acids. Archives of Biochemistry and Biophysics (1960), 87 259-65.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Misasi R, Sorice M, Griggi T, d'Agostino F, Garofalo T, Masala C, Pontieri GM, Lenti L: GM3 as a target of anti-lymphocytic ganglioside antibodies in AIDS patients. Clin Immunol Immunopathol. 1993 Jun;67(3 Pt 1):216-23. [PubMed:8500269 ]
  2. Nadler MJ, Harrison ML, Ashendel CL, Cassady JM, Geahlen RL: Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. Biochemistry. 1993 Sep 7;32(35):9250-5. [PubMed:8103677 ]