Gondoic acid

MUFA20:1Ω-11

  Overview

Stats

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

Also known as

IUPAC (11Z)-icos-11-enoic acid
Synonyms

  At a Glance

Key Points

An omega-9 fatty acid found in plant oils and nuts, notably jojoba oil.

Source

Found in plant oils and fish & seafood.

Type

Long-chain monounsaturated fatty acid with 20 carbons and one cis double bond, an omega-9 fatty acid.

Identification

  Synonyms

Ambiguity Note Gadoleic acid can represent both 11-Eicosenoic acid and 9-Eicosenoic acid.
Common Name Gondoic acid
IUPAC Name (11Z)-icos-11-enoic acid
Traditional Name —
Other Synonyms
  • cis-11-eicosenoic acid

  External IDs

General References
Wikipedia Gondoic_acid
Lipids
Lipid Maps LMFA01030085
Lipid Bank DFA0123
Swiss Lipids 000000930
PlantFA ID —
Food & Nutrition
FooDB FDB003771
INFOODS —
Chemistry / Compounds
PubChem CID 5282768
CAS 5561-99-9
ChEBI 32425
ChEMBL CHEMBL4640620
ChemSpider 4445894
InChIKey —
ZINC ID ZINC000006920439
NIKKAJI ID J12.741H
PDBe —
UCI (UniChem) —
SureChEMBL 148672
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002231
METLIN 6563
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1051
BioCyc/MetaCyc —
MetaNetX ID MNXM7404
BiGG ID —
KEGG C16526
KNApSAcK C00035628
Reactome ID —
Drugs & Pharmacology
DrugBank DB14073
DrugCentral —
BindingDB 50541547
Guide to Pharm —
Probes & Drugs PD043862
Clinical & Medical
SNOMED-CT —
MeSH C572289
NCIt Code C68361
Regulatory
NIH UNII (USA) UDX6WPL94T
FDA SRS (USA) UDX6WPL94T
NHPID (Canada) —
DTXSID (USA) DTXSID30970949
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-933-186
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
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.
Positional (3)
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.
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.
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.

Chemical Properties

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