U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H38O2
Molecular Weight 310.5145
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GONDOIC ACID

SMILES

CCCCCCCC\C=C/CCCCCCCCCC(O)=O

InChI

InChIKey=BITHHVVYSMSWAG-KTKRTIGZSA-N
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-

HIDE SMILES / InChI

Molecular Formula C20H38O2
Molecular Weight 310.5145
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

11(E)-Eicosenoic acid is a very long-chain ω-9 fatty acid that is a trans monounsaturated isomer of arachidic acid. 11(E)-Eicosenoic acid is one of several monounsaturated 20-carbon fatty acids, and is used to study phospholipid membranes. The combined C20:1 isomers constitute 70% of the total fatty acid pool in jojoba seed oil isolated from plants in the Arizona desert. 11(E)-Eicosenoic acid has been shown to inhibit glycerophosphate acyltransferase, cholinephosphotransferase and ethanolaminephosphotransferase in V79-R cells. 11(E)-Eicosenoic acid lacks the cis-double bond and has virtually no effect on telomerase activity (unlike cis-Unsaturated C20 fatty acids, which demonstrate strong telomerase inhibition and have been studied as a promising cancer therapeutic target).

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:15:23 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:23 GMT 2023
Record UNII
UDX6WPL94T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GONDOIC ACID
INCI  
INCI  
Official Name English
(Z)-EICOS-11-ENOIC ACID
Systematic Name English
(Z)-11-EICOSENOIC ACID
Systematic Name English
EICOSENOIC ACID
Systematic Name English
GONDOIC ACID [INCI]
Common Name English
11Z-EICOSENOIC ACID
Common Name English
20:1(N-9)
Code English
11-EICOSENOIC ACID, (11Z)-
Common Name English
11-EICOSENOIC ACID, CIS
Common Name English
CIS-.DELTA.11-EICOSENOIC ACID
Common Name English
Code System Code Type Description
DRUG BANK
DB14073
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
FDA UNII
UDX6WPL94T
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
MESH
C572289
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
CAS
2462-94-4
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C68361
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID30970949
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
CHEBI
32425
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
PUBCHEM
5282768
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
RXCUI
1374399
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY RxNorm
CAS
5561-99-9
Created by admin on Fri Dec 15 17:15:23 GMT 2023 , Edited by admin on Fri Dec 15 17:15:23 GMT 2023
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range)
LIPID -> FATTY ACID
TUNISIAN SOURCE
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean. Low and average are trace amounts.
LIPID -> FATTY ACID
Values are % of total.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Related Record Type Details
ACTIVE MOIETY