Heneicosapentaenoic acidHPA

PUFA21:5Ω-3

  Overview

Stats

PUFA
Type
21
Carbons
5
Double bonds
4
Bis-allylic sites
316.5
Weight · g/mol
—
Melting point
C21H32O2
Formula

Also known as

IUPAC (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
Synonyms

  At a Glance

Source

Primarily from fish & seafood. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 21 carbons and five cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Heneicosapentaenoic acid
IUPAC Name (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
Traditional Name —
Other Synonyms
  • 6Z,9Z,12Z,15Z,18Z-heneicosapentaenoic acid

  External IDs

General References
Wikipedia —
Lipids
Lipid Maps LMFA01030823
Lipid Bank —
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 11998573
CAS 24257-10-1
ChEBI 165480
ChEMBL —
ChemSpider —
InChIKey —
ZINC ID ZINC000064219883
NIKKAJI ID J662.937G
PDBe —
UCI (UniChem) 32346537
SureChEMBL 452559
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB —
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1918
BioCyc/MetaCyc —
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD020007
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) HR3EZB17BI
FDA SRS (USA) HR3EZB17BI
NHPID (Canada) —
DTXSID (USA) DTXSID30475525
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort —
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 21:5 (2)

Other fatty acids sharing the 21:5 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Heneicosapentaenoic acid
(6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
 6Z,9Z,12Z,15Z,18Z —
11998573
Category —
Conjugation Type Isolated
SMILES CC\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
all-trans-Heneicosapentaenoic Acid
(6E,9E,12E,15E,18E)-heneicosa-6,9,12,15,18-pentaenoic acid
 6E,9E,12E,15E,18E Trans
Category Isolated all-trans Omega-3 Odd-Chain Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCCC(=O)O
Description The all-trans geometric isomer of heneicosapentaenoic acid, present as a trace byproduct of high-temperature processing of marine omega-3 oils containing odd-chain HPA.
Origin Details
Origin Source Type Details
Industrial Deodorization Industrial Formed at trace levels during high-temperature deodorization and thermal stress of HPA-containing fish-oil fractions through free-radical-mediated geometric isomerization.

Chemical Properties

Name(s):
Common Name Heneicosapentaenoic acid
Abbreviation HPA
Simple Notation 21:5
Notation 21:5(n-3)
IUPAC Name (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
Semi-systematic Heneicosapentaenoic acid
Structure:
Molecular C21H32O2
SMILES CC\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z,9Z,12Z,15Z,18Z
Physical:
Weight 316.5 g/mol
Reactivity
Double Bonds 5
Bis-Allylic Carbons 4 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 120.5 ATP