Eicosatrienoic acidETE

PUFA20:3Ω-3

  Overview

Stats

PUFA
Type
20
Carbons
3
Double bonds
2
Bis-allylic sites
306.5
Weight · g/mol
—
Melting point
C20H34O2
Formula

Also known as

IUPAC (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Synonyms

  At a Glance

Source

Made in the body (endogenous synthesis); little comes from food.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and three cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Eicosatrienoic acid
IUPAC Name (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Traditional Name —
Other Synonyms
  • (11Z,14Z,17Z)-eicosa-11,14,17-trienoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030378
Lipid Bank —
Swiss Lipids 000001108
PlantFA ID —
Food & Nutrition
FooDB FDB006293
INFOODS —
Chemistry / Compounds
PubChem CID 5312529
CAS 17046-59-2
ChEBI 53460
ChEMBL CHEMBL453991
ChemSpider 4471954
InChIKey —
ZINC ID ZINC000004544257
NIKKAJI ID J323.446K
PDBe —
UCI (UniChem) 68989
SureChEMBL 25423
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0060039
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1051
BioCyc/MetaCyc —
MetaNetX ID MNXM8271
BiGG ID —
KEGG C16522
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB 50269535
Guide to Pharm —
Probes & Drugs PD020548
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) —
FDA SRS (USA) —
NHPID (Canada) —
DTXSID (USA) DTXSID60920492
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-018-848
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:3 (6)

Other fatty acids sharing the 20:3 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Eicosatrienoic acid
(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
 11Z,14Z,17Z —
5312529
Category —
Conjugation Type Isolated
SMILES CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (5)
Dihomo-γ-linolenic acid
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
 8Z,11Z,14Z —
5280581
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Mead acid
(5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
 5Z,8Z,11Z —
5312531
Category —
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
Sciadonic acid
(5Z,11Z,14Z)-icosa-5,11,14-trienoic acid
 5Z,11Z,14Z —
445084
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\CCCC\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
5Z,8Z,14Z-Eicosatrienoic Acid
(5Z,8Z,14Z)-icosa-5,8,14-trienoic acid
 5Z,8Z,14Z —
6439516
Category Non-Methylene-Interrupted Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/CCCC\C=C/C\C=C/CCCC(=O)O
Description A non-methylene-interrupted polyunsaturated fatty acid found in gymnosperm seed oils, generated by elongation of pinolenic acid and co-occurring with sciadonic acid.
Origin Details
Origin Source Type Details
Pinaceae Seed Oils Natural Detected in seed oils of Pinaceae as the C20 elongation product of pinolenic acid (5,9,12-18:3).
Dihomopinolenic Acid
(7Z,11Z,14Z)-icosa-7,11,14-trienoic acid
 7Z,11Z,14Z —
5312533
Category Non-Methylene-Interrupted Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CC\C=C/CCCCCC(=O)O
Description A non-methylene-interrupted omega-6 polyunsaturated fatty acid found in Taxaceae seed lipids as the C20 elongation/desaturation product of taxoleic acid.
Origin Details
Origin Source Type Details
Taxus Seed Oils Natural Present in seed oils of Taxus species, generated by chain elongation and Δ14 desaturation from taxoleic acid (5,9-18:2).

Chemical Properties

Name(s):
Common Name Eicosatrienoic acid
Abbreviation ETE
Simple Notation 20:3
Notation 20:3(n-3)
IUPAC Name (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Semi-systematic Eicosatrienoic acid
Structure:
Molecular C20H34O2
Structure CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)9COOH
SMILES CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O
Cis / Trans cis
E-Z 11Z,14Z,17Z
Physical:
Weight 306.5 g/mol
Reactivity
Double Bonds 3
Bis-Allylic Carbons 2 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 129.5 ATP