Gadoleic acid

MUFA20:1Ω-9

  Overview

Stats

MUFA
Type
20
Carbons
1
Double bonds
0
Bis-allylic sites
310.5
Weight · g/mol
23.5 °C
Melting point
C20H38O2
Formula

Also known as

IUPAC (Z)-icos-9-enoic acid

  At a Glance

Key Points

A prominent component of fish oils such as cod-liver oil (named from Gadus, cod).

Source

Primarily from fish & seafood; also in plant oils.

Type

Long-chain monounsaturated fatty acid with 20 carbons and one cis double bond, an omega-11 fatty acid.

Identification

  Synonyms

Ambiguity Note Gadoleic acid can represent both 11-Eicosenoic acid and 9-Eicosenoic acid.
Common Name Gadoleic acid
IUPAC Name (Z)-icos-9-enoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia Gadoleic_acid
Lipids
Lipid Maps LMFA01030084
Lipid Bank DFA0122
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB FDB003771
INFOODS —
Chemistry / Compounds
PubChem CID 5282767
CAS 29204-02-2
ChEBI 32419
ChEMBL —
ChemSpider 4445894
InChIKey —
ZINC ID ZINC000064622623
NIKKAJI ID J17.206E
PDBe —
UCI (UniChem) 1097783
SureChEMBL 245176
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0062436
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1693
BioCyc/MetaCyc —
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK C00053190
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD143267
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68368
Regulatory
NIH UNII (USA) 474JWU0SQ6
FDA SRS (USA) 474JWU0SQ6
NHPID (Canada) —
DTXSID (USA) DTXSID101045292
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-047-972-053
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:1 (4)

Other fatty acids sharing the 20:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Gadoleic acid
(Z)-icos-9-enoic acid
 11Z —
5282767
Category —
Conjugation Type —
SMILES CCCCCCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
Trans-gondoic acid
(E)-icos-11-enoic acid
 11E —
5282769
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (2)
Paullinic acid
(Z)-icos-13-enoic acid
 13Z —
5312518
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Gondoic acid
(11Z)-icos-11-enoic acid
 9Z —
5282768
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Gadoleic acid
Simple Notation 20:1
Notation 20:1(n-11)
IUPAC Name (Z)-icos-9-enoic acid
Structure:
Molecular C20H38O2
Structure CH3(CH2)9CH=CH(CH2)7COOH
SMILES CCCCCCCCCC\C=C/CCCCCCCC(=O)O
Cis / Trans cis
E-Z 11Z
Physical:
Weight 310.5 g/mol
Melting Point 23.5 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 132.5 ATP