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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2020-02-26 21:23:59 UTC
HMDB IDHMDB0002261
Secondary Accession Numbers
  • HMDB02261
Metabolite Identification
Common Name2-Hydroxymyristic acid
Description2-Hydroxymyristic acid, also known as a-hydroxymyristate or a-hydroxy-N-tetradecylate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 2-Hydroxymyristic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752239
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
a-HydroxymyristateGenerator
a-Hydroxymyristic acidGenerator
alpha-HydroxymyristateGenerator
Α-hydroxymyristateGenerator
Α-hydroxymyristic acidGenerator
2-HydroxymyristateGenerator
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
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
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

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 Solubility0.019 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9700000000-8493ca6732d2b7ebf6b1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9242000000-206629d5379d5a4a3a86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0390000000-fa16fe269769b95e9682Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ot-3930000000-58ff17a1c4711e739574Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-1ceac1323899f5bc74f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-7ba586681c0bf7368a66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-0960000000-5b0f96b6ff1eb7d2407cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-6900000000-a272f854b23f304deab7Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]