Sciadonic acidSciA

PUFA20:3Ω-6

  Overview

Stats

PUFA
Type
20
Carbons
3
Double bonds
1
Bis-allylic sites
306.5
Weight · g/mol
—
Melting point
C20H34O2
Formula

Also known as

IUPAC (5Z,11Z,14Z)-icosa-5,11,14-trienoic acid
Synonyms

  At a Glance

Source

Found in plants.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and three cis double bonds, an omega-6 fatty acid.

Identification

  Synonyms

Common Name Sciadonic acid
IUPAC Name (5Z,11Z,14Z)-icosa-5,11,14-trienoic acid
Traditional Name —
Other Synonyms
  • all-cis-5,11,14-eicosatrienoic acid
  • Δ5,11,14-20:3

  External IDs

General References
Wikipedia Sciadonic acid
Lipids
Lipid Maps LMFA01030380
Lipid Bank —
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 445084
CAS 7019-85-4
ChEBI 82832
ChEMBL —
ChemSpider —
InChIKey —
ZINC ID ZINC000005972968
NIKKAJI ID —
PDBe —
UCI (UniChem) 22740738
SureChEMBL 1033821
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB —
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS3683
BioCyc/MetaCyc —
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD019618
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 69Y3H52QB5
FDA SRS (USA) 69Y3H52QB5
NHPID (Canada) —
DTXSID (USA) DTXSID601317197
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
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.
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.
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.
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 Sciadonic acid
Abbreviation SciA
Simple Notation 20:3
Notation 20:3(n-6) NMI Δ5,11,14
IUPAC Name (5Z,11Z,14Z)-icosa-5,11,14-trienoic acid
Structure:
Molecular C20H34O2
SMILES CCCCC/C=C\C/C=C\CCCC\C=C/CCCC(=O)O
Cis / Trans cis
E-Z 5Z,11Z,14Z
Physical:
Weight 306.5 g/mol
Reactivity
Double Bonds 3
Bis-Allylic Carbons 1 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 129.5 ATP