| 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 molecliar 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 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(Z,Z)-7,10-Hexadecadienoic acidChEBI
(Z,Z)-Hexadeca-7,10-dienoic acidChEBI
7-cis,10-cis-Hexadecadienoic acidChEBI
C16:2N-6,9ChEBI
(Z,Z)-7,10-HexadecadienoateGenerator
7Z,10Z-HexadecadienoateGenerator
(Z,Z)-Hexadeca-7,10-dienoateGenerator
7-cis,10-cis-HexadecadienoateGenerator
| Chemical Formlia |
C16H28O2
| Average Molecliar Weight |
252.3923
| Monoisotopic Molecliar Weight |
252.20893014
| IUPAC Name |
(7Z,10Z)-hexadeca-7,10-dienoic acid
| Traditional Name |
7Z,10Z-hexadecadienoic acid
| CAS Registry Number |
28290-73-5
| SMILES |
CCCCCC=C/CC=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 |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Long-chain fatty acids
| Alternative Parents |
Unsaturated fatty acids
Straight chain fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
hexadecadienoic acid (CHEBI:86147 )
Unsaturated fatty acids (LMFA01030807 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.000667 mg/mLALOGPS
logP6.23ALOGPS
logP5.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity79.32 m3·mol-1ChemAxon
Polarizability31.67 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite 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
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00477
| Metagene Link |
HMDB00477
| METLIN ID |
5464
| PubChem Compound |
13932172
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: AM-2394
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 |
- 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 ]
|
PMID: 16028916