Record Information
Version1.0
Creation date2011-04-11 18:33:54 UTC
Update date2018-01-23 20:19:26 UTC
Primary IDFDB021831
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid
DescriptionDocosapentaenoic acid (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source. There are three functions of docosapentaenoic acid. The most important is as part of phospholipids in all animal cellular membranes: a deficiency of docosapentaenoic acid leads to faulty membranes being formed. A second is in the transport and oxidation of cholesterol: clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes: sudden failure of growth, lesions of skin and kidney and connective tissue, erythrocyte fragility, impaired fertility, uncoupling of oxidation and phosphorylation. In man pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common on Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid. (PMID: 6469703) [HMDB]. 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid is found in many foods, some of which are green zucchini, green bell pepper, green bean, and red bell pepper.
CAS Number24880-45-3
Structure
Thumb
Synonyms
SynonymSource
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acidChEBI
(all Z)-7,10,13,16,19-Docosapentaenoic acidChEBI
all-cis-7,10,13,16,19-Docosapentaenoic acidChEBI
cis-7,10,13,16,19-Docosapentaenoic acidChEBI
Clupanodonic acidChEBI
Docosa-7C,10C,13C,16C,19C-pentaensaeureChEBI
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acidChEBI
Docosapentaenoic acidChEBI
DPAChEBI
DPAn-3ChEBI
7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acidKegg
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoateGenerator
(all Z)-7,10,13,16,19-DocosapentaenoateGenerator
all-cis-7,10,13,16,19-DocosapentaenoateGenerator
cis-7,10,13,16,19-DocosapentaenoateGenerator
ClupanodonateGenerator
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoateGenerator
DocosapentaenoateGenerator
7Z,10Z,13Z,16Z,19Z-DocosapentaenoateGenerator
Docosapentaenoate (22N-3)Generator
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoateHMDB
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acidHMDB
7,10,13,16,19-DocosapentaenoateHMDB
7,10,13,16,19-Docosapentaenoic acidHMDB
4,7,10,13,16-Docosapentaenoic acidHMDB
Docosa-4,7,10,13,16-pentaenoic acidHMDB
Docosa-4,7,10,13,16-pentaenoic acid 5-(14)C-labeled CPD, (all-Z)-isomerHMDB
Docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomerHMDB
Docosapentaenoic acid, (all Z)-isomerHMDB
FA(22:5(7Z,10Z,13Z,16Z,19Z))HMDB
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acidMeSH
Docosapentaenoic acid (C22:5 N6)MeSH
7,10,13,16,19-Docosapentaenoic acid, (Z,Z,Z,Z,e)-isomerMeSH
7,10,13,16,19-Docosapentaenoic acid, lithium saltMeSH
7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomerMeSH
7,10,13,16,19-Docosapentaenoic acid, lithium salt, (all-Z)-isomerMeSH
Docosapentaenoic acid (C22:5 N3)MeSH
Osbond acidMeSH
C22:5n-3,6,9,12,15manual
Docosa-7c,10c,13c,16c,19c-pentaensaeureChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.08ALOGPS
logP7.11ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.27 m³·mol⁻¹ChemAxon
Polarizability40.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H34O2
IUPAC name(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
InChI IdentifierInChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyYUFFSWGQGVEMMI-JLNKQSITSA-N
Isomeric SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
Classification
Description belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID4593750
ChEMBL IDCHEMBL496634
KEGG Compound IDC16513
Pubchem Compound ID5497182
Pubchem Substance IDNot Available
ChEBI ID53488
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06528
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2218032
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDocosapentaenoic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).