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Record Information
Version3.6
Creation Date2006-05-22 14:17:31 UTC
Update Date2016-02-11 01:05:12 UTC
HMDB IDHMDB02000
Secondary Accession NumbersNone
Metabolite Identification
Common NameMyristoleic acid
DescriptionMyristoleic acid is a monounsaturated fatty acid that represent approximately 0.3 - 0.7% of the total fatty acid composition of adipose tissue triacylglycerol in human. (PMID 10393134 ). It has been suggested that his cytotoxic and effective cell death inducer activity could be used for the treatment of prostate cancer. (PMID 11304730 ).
Structure
Thumb
Synonyms
ValueSource
(9Z)-Tetradecenoic acidChEBI
9-Tetradecenoic acidChEBI
9Z-Tetradecenoic acidChEBI
cis-9-Tetradecenoic acidChEBI
cis-Delta(9)-Tetradecenoic acidChEBI
cis-Tetradec-9-enoic acidChEBI
(9Z)-TetradecenoateGenerator
(Z)-Tetradec-9-enoateGenerator
9-TetradecenoateGenerator
9Z-TetradecenoateGenerator
cis-9-TetradecenoateGenerator
cis-delta(9)-TetradecenoateGenerator
cis-δ(9)-tetradecenoateGenerator
cis-δ(9)-tetradecenoic acidGenerator
cis-Tetradec-9-enoateGenerator
(9Z)-Tetradec-9-enoateHMDB
(9Z)-Tetradec-9-enoic acidHMDB
MyristoleateHMDB
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name(9Z)-tetradec-9-enoic acid
Traditional Namemyristoleic acid
CAS Registry Number544-64-9
SMILES
CCCC\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChI KeyInChIKey=YWWVWXASSLXJHU-WAYWQWQTSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and 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 Solubility0.0022 mg/mLALOGPS
logP5.69ALOGPS
logP5.01ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m3·mol-1ChemAxon
Polarizability28.75 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0aou-9100000000-1823acbf402fe87fba5bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue Location
  • Adipose Tissue
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.016 +/- 0.733 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
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 IDFDB012633
KNApSAcK IDC00001229
Chemspider ID4444564
KEGG Compound IDC08322
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyristoleic acid
NuGOwiki LinkHMDB02000
Metagene LinkHMDB02000
METLIN ID6424
PubChem Compound5281119
PDB IDNot Available
ChEBI ID27781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mamalakis G, Kafatos A, Board S: Type A behavior and adipose tissue linoleic acid: implications for stress management. J Am Coll Nutr. 1994 Jun;13(3):292-7. [8077579 ]
  2. Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7. [10393134 ]
  3. Iguchi K, Okumura N, Usui S, Sajiki H, Hirota K, Hirano K: Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate. 2001 Apr;47(1):59-65. [11304730 ]