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Showing metabocard for 7Z,10Z-Hexadecadienoic acid (HMDB00477)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:26:58 -0600
HMDB ID HMDB00477
Secondary Accession Numbers None
Metabolite Identification
Common Name 7Z,10Z-Hexadecadienoic acid
Description 7Z,10Z-Hexadecadienoic acid is a conjugated dienoic fatty acid metabolite of conjugated linoleic acid (CLA). CLAs are a naturally occurring group of positional and geometric isomers of linoleic acid, with potential beneficial effects on atherosclerosis, carcinogenesis or obesity in human. Although the molecular mechanisms are largely unknown, it has been proposed that the anti-atherogenic actions comprise reduction of membrane-bound arachidonic acid and peroxisome proliferator-activated receptor (PPAR)-γ-dependent inhibition of Nuclear Factor kappa B (NF-κB) activation and subsequently reduced prostanoid release. (PMID 16275160 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (Z,Z)-7,10-Hexadecadienoate
  2. (Z,Z)-7,10-Hexadecadienoic acid
  3. 7Z,10Z-Hexadecadienoate
  4. 7Z,10Z-Hexadecadienoic acid
Chemical Formula C16H28O2
Average Molecular Weight 252.3923
Monoisotopic Molecular Weight 252.20893014
IUPAC Name (7Z,10Z)-hexadeca-7,10-dienoic acid
Traditional IUPAC Name (7Z,10Z)-hexadeca-7,10-dienoic acid
CAS Registry Number 28290-73-5
SMILES CCCCC\C=C/C\C=C/CCCCCC(O)=O
InChI Identifier InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-
InChI Key WPJGPAAPSBVXNU-HZJYTTRNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Expected and Not 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
  • Cytoplasm
  • Extracellular
  • Membrane
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 6.670E-04 g/L ALOGPS
LogP 6.23 ALOGPS
LogP 5.53 ChemAxon
LogS -5.58 ALOGPS
pKa (strongest acidic) 4.96 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 79.32 ChemAxon
Polarizability 31.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
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 FDB022064
KNApSAcK ID Not Available
Chemspider ID 13628094 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00477 Link_out
Metagene Link HMDB00477 Link_out
METLIN ID 5464 Link_out
PubChem Compound 13932172 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Beaudoin, Adrien; Martin, Genevieve. Method of extracting lipids from marine and aquatic animal tissues. PCT Int. Appl. (2000), 58 pp. CODEN: PIXXD2 WO 2000023546 A1 20000427 CAN 132:305471 AN 2000:278070
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Muller A, Ringseis R, Dusterloh K, Gahler S, Eder K, Steinhart H: Detection of conjugated dienoic fatty acids in human vascular smooth muscle cells treated with conjugated linoleic acid. Biochim Biophys Acta. 2005 Dec 15;1737(2-3):145-51. Epub 2005 Oct 21. Pubmed: 16275160 Link_out