Showing Compound 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid (FDB021831)

Record Information

Version

1.0

Creation date

2011-04-11 18:33:54 UTC

Update date

2019-11-26 03:20:55 UTC

Primary ID

FDB021831

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid

Description

Docosapentaenoic 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 Number

24880-45-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid	ChEBI
(all Z)-7,10,13,16,19-Docosapentaenoic acid	ChEBI
all-cis-7,10,13,16,19-Docosapentaenoic acid	ChEBI
cis-7,10,13,16,19-Docosapentaenoic acid	ChEBI
Clupanodonic acid	ChEBI
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid	ChEBI
Docosapentaenoic acid	ChEBI
DPA	ChEBI
DPAn-3	ChEBI
7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid	Kegg
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoate	Generator
(all Z)-7,10,13,16,19-Docosapentaenoate	Generator
all-cis-7,10,13,16,19-Docosapentaenoate	Generator
cis-7,10,13,16,19-Docosapentaenoate	Generator
Clupanodonate	Generator
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoate	Generator
Docosapentaenoate	Generator
7Z,10Z,13Z,16Z,19Z-Docosapentaenoate	Generator
Docosapentaenoate (22N-3)	Generator
7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomer	MeSH
Docosapentaenoic acid (C22:5 N3)	MeSH
Osbond acid	MeSH
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acid	MeSH
7,10,13,16,19-Docosapentaenoic acid	MeSH
Docosapentaenoic acid, (all Z)-isomer	MeSH
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate	HMDB
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid	HMDB
7,10,13,16,19-Docosapentaenoate	HMDB
FA(22:5(7Z,10Z,13Z,16Z,19Z))	HMDB
(7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-Docosapentaenoic acid	HMDB
(all-Z)-7,10,13,16,19-Docosapentaenoic acid	HMDB
FA(22:5n3)	HMDB
delta7,10,13,16,19-Docosapentaenoic acid	HMDB
omega3-Docosapentaenoic acid	HMDB
Δ7,10,13,16,19-Docosapentaenoic acid	HMDB
ω3-Docosapentaenoic acid	HMDB
C22:5n-3,6,9,12,15	manual
Docosa-7c,10c,13c,16c,19c-pentaensaeure	ChEBI

Predicted Properties

Property	Value	Source
Water Solubility	0.00012 g/L	ALOGPS
logP	7.08	ALOGPS
logP	7.11	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	110.27 m³·mol⁻¹	ChemAxon
Polarizability	40.1 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C22H34O2

IUPAC name

(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid

InChI Identifier

InChI=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 Key

YUFFSWGQGVEMMI-JLNKQSITSA-N

Isomeric SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O

Average Molecular Weight

330.5042

Monoisotopic Molecular Weight

330.255880332

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very 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 Framework

Aliphatic acyclic compounds

External Descriptors

omega-3 fatty acid (CHEBI:53488 )
docosapentaenoic acid (CHEBI:53488 )
Docosanoids (C16513 )
Polyunsaturated fatty acids (C16513 )
Docosanoids (LMFA04000044 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-5491000000-56de363323dabc6f26e3	Spectrum
Predicted GC-MS	7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009i-9583000000-943203f8659c9ab3cac4	Spectrum
Predicted GC-MS	7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-0090000000-260dcf8cd2e9cacf0e81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0090000000-b359128b4a9edc7dc9ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-01x3-0492000000-89d3794a87bea421691b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0039000000-405cbfa338b34ddb7441	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5793000000-59855762e7bce0a8ec9d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avv-8970000000-49596865551dfe04eaa1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-4d8832b1fd953fd8ec08	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-1039000000-f6df0e4a8ec7c01d9955	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9130000000-a69f7e9f82c75012f728	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-f4bd181f937819513660	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1009000000-fd8104aee9b78a72f4db	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9221000000-a71d2d6e07928441d5ef	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-2329000000-918ad0c35d9079c18ee1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4911000000-cca43fd70d0980b4845e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9700000000-ca068d510d72f2bb000e	2021-09-23	View Spectrum