Mead acid

PUFA20:3Ω-9

  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 (5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
Synonyms

  At a Glance

Key Points

Made by the body only during essential-fatty-acid deficiency — its rise in blood is a marker of that deficiency; abundant in cartilage.

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-9 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Mead acid
IUPAC Name (5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
Traditional Name —
Other Synonyms
  • C20:3n-9,12,15
  • (5Z,8Z,11Z)-eicosa-5,8,11-trienoic acid

  External IDs

General References
Wikipedia Mead_acid
Lipids
Lipid Maps LMFA01030381
Lipid Bank —
Swiss Lipids 000001063
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5312531
CAS 20590-32-3
ChEBI 72865
ChEMBL CHEMBL1865841
ChemSpider 4471956
InChIKey —
ZINC ID ZINC000008860488
NIKKAJI ID —
PDBe —
UCI (UniChem) 1145268
SureChEMBL 842264
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0010378
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS11748
BioCyc/MetaCyc —
MetaNetX ID MNXM37925
BiGG ID —
KEGG C21938
KNApSAcK C00052345
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD020549
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68390
Regulatory
NIH UNII (USA) JQS194YH3X
FDA SRS (USA) JQS194YH3X
NHPID (Canada) —
DTXSID (USA) DTXSID10920487
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort —
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
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.
Positional (5)
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.
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.
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 Mead acid
Simple Notation 20:3
Notation 20:3(n-9)
IUPAC Name (5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
Structure:
Molecular C20H34O2
SMILES CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
Cis / Trans cis
E-Z 5Z,8Z,11Z
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