Osbond acidDPA n-6

PUFA22:5Ω-6

  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 (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
Systematic Docosapentaenoic Acid
Synonyms

  At a Glance

Source

Found in fish & seafood. Also made by the body.

Type

Very-long-chain polyunsaturated fatty acid with 22 carbons and five cis double bonds, an omega-6 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 Osbond acid
IUPAC Name (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
Traditional Name —
Other Synonyms
  • all-cis-4,7,10,13,16-Docosapentaenoic acid
  • Docosapentaenoic acid (22n-6)
  • (All-Z)-4,7,10,13,16-docosapentaenoic acid
  • 4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid
  • 4,7,10,13,16-Docosapentaenoic acid, (all-Z)-
  • C22:5n-6,9,12,15,18
  • 4,7,10,13,16-Docosapentaenoic acid, (4Z,7Z,10Z,13Z,16Z)-
  • all-cis-docosa-4,7,10,13,16-pentaenoic acid
  • 22:5(4Z,7Z,10Z,13Z,16Z)

  External IDs

General References
Lipids
Lipid Maps LMFA04000064
Lipid Bank —
Swiss Lipids 000001208
PlantFA ID —
Food & Nutrition
FooDB FDB022774
INFOODS —
Chemistry / Compounds
PubChem CID 6441454
CAS 25182-74-5
ChEBI 65136
ChEMBL —
ChemSpider 4945614
InChIKey —
ZINC ID ZINC000033955138
NIKKAJI ID J381.482C
PDBe —
UCI (UniChem) —
SureChEMBL 452175
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0001976
METLIN 6412
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS106
BioCyc/MetaCyc —
MetaNetX ID MNXM28472
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank DB14088
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD018161
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 7S686LQT6T
FDA SRS (USA) 7S686LQT6T
NHPID (Canada) —
DTXSID (USA) DTXSID60912352
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-044-561-988
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
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.
Positional (2)
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.
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.

Chemical Properties

Name(s):
Common Name Osbond acid
Abbreviation DPA n-6
Simple Notation 22:5
Notation 22:5(n-6)
IUPAC Name (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
Semi-systematic Docosapentaenoic Acid
Structure:
Molecular C22H34O2
SMILES CCCCC\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
Cis / Trans cis
E-Z 4Z,7Z,10Z,13Z,16Z
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