Docosapentaenoic acidDPA

PUFA22:5Ω-3

  Overview

Stats

PUFA
Type
22
Carbons
5
Double bonds
4
Bis-allylic sites
330.5
Weight · g/mol
—
Melting point
C22H34O2
Formula

Also known as

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

  At a Glance

Key Points

A 22:5 omega-3, structurally between EPA and DHA; its n-3 and n-6 isomers belong to separate PUFA classes the body cannot interconvert.

Source

Primarily from fish & seafood; also in meat. Also made by the body.

Type

Very-long-chain polyunsaturated fatty acid with 22 carbons and five cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Ambiguity Note The common name Docosapentaenoic Acid (DPA) can represent either the omega-3 or omega-6 variants.
Common Name Docosapentaenoic acid
IUPAC Name (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
Traditional Name Clupanodonic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA04000044
Lipid Bank DFA0129
Swiss Lipids 000000929
PlantFA ID —
Food & Nutrition
FooDB FDB021831
INFOODS —
Chemistry / Compounds
PubChem CID 5497182
CAS 24880-45-3
ChEBI 53488
ChEMBL CHEMBL496634
ChemSpider 4593750
InChIKey —
ZINC ID ZINC000008860491
NIKKAJI ID J490.555E
PDBe —
UCI (UniChem) —
SureChEMBL 20748
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0006528
METLIN 194
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1115
BioCyc/MetaCyc CPD-13792
MetaNetX ID MNXM6529
BiGG ID 2218032
KEGG C16513
KNApSAcK C00052249
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50269224
Guide to Pharm —
Probes & Drugs PD020552
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68334
Regulatory
NIH UNII (USA) NS3OZT14QT
FDA SRS (USA) NS3OZT14QT
NHPID (Canada) —
DTXSID (USA) DTXSID6074758
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-940-987
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 22:5 (3)

Other fatty acids sharing the 22:5 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Docosapentaenoic acid
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
 7Z,10Z,13Z,16Z,19Z —
5497182
Category —
Conjugation Type Isolated
SMILES CC/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
Geometric (1)
all-trans-Docosapentaenoic Acid n-3
(7E,10E,13E,16E,19E)-docosa-7,10,13,16,19-pentaenoic acid
 7E,10E,13E,16E,19E Trans
Category Isolated all-trans Omega-3 Very Long-Chain Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCCCC(=O)O
Description The all-trans geometric isomer of DPA n-3, present as a trace byproduct during high-temperature deodorization and refining of marine omega-3 oils.
Origin Details
Origin Source Type Details
Industrial Deodorization Industrial Formed at trace levels during high-temperature deodorization and thermal stress of DPA-containing marine oil fractions through free-radical-mediated geometric isomerization.
Positional (1)
Osbond acid
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
 4Z,7Z,10Z,13Z,16Z —
6441454
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Docosapentaenoic acid
Abbreviation DPA
Simple Notation 22:5
Notation 22:5(n-3)
IUPAC Name (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
Traditional Name Clupanodonic acid
Semi-systematic Docosapentaenoic acid
Structure:
Molecular C22H34O2
SMILES CC/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
Cis / Trans cis
E-Z 7Z,10Z,13Z,16Z,19Z
Physical:
Weight 330.5 g/mol
Reactivity
Double Bonds 5
Bis-Allylic Carbons 4 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 10
ATP Yield (Net) 140.5 ATP