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Record Information
Version3.6
Creation Date2006-05-22 14:17:45 UTC
Update Date2016-02-11 01:05:29 UTC
HMDB IDHMDB02261
Secondary Accession NumbersNone
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-HydroxytetradecanoateGenerator
a-HydroxymyristateGenerator
a-Hydroxymyristic acidGenerator
alpha-HydroxymyristateGenerator
α-hydroxymyristateGenerator
α-hydroxymyristic acidGenerator
2-Hydroxy-myristic-acidHMDB
2-HydroxymyristateHMDB
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 KeyInChIKey=JYZJYKOZGGEXSX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity69.37 m3·mol-1ChemAxon
Polarizability30.7 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB02261
Metagene LinkHMDB02261
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. [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. [8103677 ]