Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2022-03-07 02:49:14 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
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point51.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point377.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility17.82 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.150 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.96131661259
DarkChem[M-H]-161.1931661259
DeepCCS[M+H]+162.73730932474
DeepCCS[M-H]-158.71630932474
DeepCCS[M-2H]-196.22730932474
DeepCCS[M+Na]+171.92630932474
AllCCS[M+H]+166.032859911
AllCCS[M+H-H2O]+162.732859911
AllCCS[M+NH4]+169.132859911
AllCCS[M+Na]+170.032859911
AllCCS[M-H]-164.332859911
AllCCS[M+Na-2H]-165.232859911
AllCCS[M+HCOO]-166.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxymyristic acidCCCCCCCCCCCCC(O)C(O)=O2890.7Standard polar33892256
2-Hydroxymyristic acidCCCCCCCCCCCCC(O)C(O)=O1858.5Standard non polar33892256
2-Hydroxymyristic acidCCCCCCCCCCCCC(O)C(O)=O1931.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxymyristic acid,1TMS,isomer #1CCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O1986.3Semi standard non polar33892256
2-Hydroxymyristic acid,1TMS,isomer #2CCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C1952.9Semi standard non polar33892256
2-Hydroxymyristic acid,2TMS,isomer #1CCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C2029.7Semi standard non polar33892256
2-Hydroxymyristic acid,1TBDMS,isomer #1CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O2218.6Semi standard non polar33892256
2-Hydroxymyristic acid,1TBDMS,isomer #2CCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C(C)(C)C2185.8Semi standard non polar33892256
2-Hydroxymyristic acid,2TBDMS,isomer #1CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2468.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9700000000-8493ca6732d2b7ebf6b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9242000000-206629d5379d5a4a3a862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxymyristic acid 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-Hydroxymyristic acid 10V, Positive-QTOFsplash10-002b-0390000000-fa16fe269769b95e96822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Positive-QTOFsplash10-05ot-3930000000-58ff17a1c4711e7395742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Positive-QTOFsplash10-052f-9400000000-1ceac1323899f5bc74f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Negative-QTOFsplash10-0006-0290000000-7ba586681c0bf7368a662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Negative-QTOFsplash10-002e-0960000000-5b0f96b6ff1eb7d2407c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Negative-QTOFsplash10-014m-6900000000-a272f854b23f304deab72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Negative-QTOFsplash10-0006-0090000000-5bf7291211ccfc8403712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Negative-QTOFsplash10-0006-1290000000-b279ed37b3233bd67aba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Negative-QTOFsplash10-0006-9000000000-19fc4b5fb13d8c68f49b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Positive-QTOFsplash10-0002-7590000000-69d3171bbb95f941fb9f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Positive-QTOFsplash10-0a4i-9200000000-43bbc1f0c7641b18f6f32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-5a9991dd3dc9260adadb2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents IDrw1027761
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 ]