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Record Information
Version4.0
Creation Date2006-05-22 14:17:31 UTC
Update Date2017-09-27 08:24:11 UTC
HMDB IDHMDB0002000
Secondary Accession Numbers
  • HMDB02000
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
(Z)-Tetradec-9-enoic acidChEBI
9-Tetradecenoic acidChEBI
9Z-Tetradecenoic acidChEBI
cis-9-Tetradecenoic acidChEBI
cis-Delta(9)-Tetradecenoic acidChEBI
cis-Tetradec-9-enoic acidChEBI
(9Z)-TetradecenoateGenerator
MyristoleateGenerator
(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
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 KeyYWWVWXASSLXJHU-WAYWQWQTSA-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
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

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 Solubility0.0022 g/LALOGPS
logP5.69ALOGPS
logP5.01ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability28.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-57b079c6d11a9714cb51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-4fcda40660e1f5947eb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9120000000-50121015a2477be41becView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0595-9000000000-98c3d58fb9e1e7c41c90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004i-0090000000-e588f40ae851251aee81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0390000000-6a2bf4ff780562d5fdd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-6930000000-bd53c7ac25c8930728e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-cd017bd3efd7fa06ee6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-c6a068748e37ad83d1d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1590000000-999dd13c5871dbb32a3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-97121a85c8e202172ecfView in MoNA
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
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.016 +/- 0.733 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
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
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. [PubMed: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. [PubMed: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. [PubMed:11304730 ]