Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Myristoleic acid (HMDB02000)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:31 -0600
Update Date 2013-02-08 17:11:10 -0700
HMDB ID HMDB02000
Secondary Accession Numbers None
Metabolite Identification
Common Name Myristoleic acid
Description Myristoleic 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 Link_out). It has been suggested that his cytotoxic and effective cell death inducer activity could be used for the treatment of prostate cancer. (PMID 11304730 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (9Z)-tetradec-9-enoate
  2. (9Z)-tetradec-9-enoic acid
  3. (9Z)-Tetradecenoate
  4. (9Z)-Tetradecenoic acid
  5. (Z)-Tetradec-9-enoate
  6. (Z)-Tetradec-9-enoic acid
  7. 9-Tetradecenoate
  8. 9-Tetradecenoic acid
  9. 9Z-Tetradecenoate
  10. 9Z-Tetradecenoic acid
  11. cis-9-Tetradecenoate
  12. cis-9-Tetradecenoic acid
  13. cis-delta(9)-Tetradecenoate
  14. cis-delta(9)-Tetradecenoic acid
  15. Myristoleate
Chemical Formula C14H26O2
Average Molecular Weight 226.355
Monoisotopic Molecular Weight 226.193280076
IUPAC Name (9Z)-tetradec-9-enoic acid
Traditional IUPAC Name myristoleic acid
CAS Registry Number 544-64-9
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 Key YWWVWXASSLXJHU-WAYWQWQTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monounsaturated fatty acids(KEGG)
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated fatty acids(KEGG)
  • Unsaturated fatty acids(Lipidmaps)
  • long-chain fatty acid(ChEBI)
  • tetradecenoic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0022 g/L ALOGPS
LogP 5.69 ALOGPS
LogP 5.01 ChemAxon
LogS -5.00 ALOGPS
pKa (strongest acidic) 4.99 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 69 ChemAxon
Polarizability 28.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
2.016 +/- 0.733 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012633
KNApSAcK ID C00001229 Link_out
Chemspider ID 4444564 Link_out
KEGG Compound ID C08322 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Myristoleic acid Link_out
NuGOwiki Link HMDB02000 Link_out
Metagene Link HMDB02000 Link_out
METLIN ID 6424 Link_out
PubChem Compound 5281119 Link_out
PDB ID Not Available
ChEBI ID 27781 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out