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Details

Stereochemistry ACHIRAL
Molecular Formula C24H46O2
Molecular Weight 366.6208
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NERVONIC ACID

SMILES

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

InChI

InChIKey=GWHCXVQVJPWHRF-KTKRTIGZSA-N
InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-

HIDE SMILES / InChI

Molecular Formula C24H46O2
Molecular Weight 366.6208
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors. Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. Nervonic acid (C24:1), a component of membrane sphingolipids and phosphatidylethanolamines, may be a useful predictor of chronic kidney disease mortality and diabetes. Nervonic acid oils are being studied for pharmaceutical, nutraceutical and industrial applications. Nervonic acid is a major component of Lunaria oil. There is increasing evidence that dietary supplementation with nervonic acid is healthy for babies and infants during the early stage of brain development. Nervonic acid has been reported to reduce the shaking associated with Parkinson’s disease and the numbness caused by multiple sclerosis. It also has potential for treating schizophrenia and reducing early Alzheimer’s symptoms.

Originator

Curator's Comment: Nervonic acid (24 carbon atoms) was first discovered by Tsujimoto M. in 1927 in fats of Elasmobranch fishes

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Arachidonic acid predominates in the membrane phosphoglycerides of the early and term human placenta.
2005 Nov
Serum lipid fatty acids and temporal processing acuity in children with oral clefts.
2006 Apr
Site-directed mutational analysis of structural interactions of low molecule compounds binding to the N-terminal 8 kDa domain of DNA polymerase beta.
2006 Nov 10
Patents

Sample Use Guides

Since Nervonic acid is almost insoluble in water, it often sold in the form of capsules. Generally speaking, two capsules orally every time, and two doses or two times a day, one in the morning, and the other in the evening. The recommended dosage ranges from 200mg to 300mg of pure nervonic acid.
Route of Administration: Oral
In Vitro Use Guide
Nervonic acid (NA) most effectively inhibited calf DNA polymerase a activity; its minimum inhibitory concentration MIC was 2 uM. NA 10 uM completely suppressed the activities of both polymerases (calf DNA polymerase a and rat DNA polymerase b).
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:14:21 UTC 2023
Edited
by admin
on Sat Dec 16 05:14:21 UTC 2023
Record UNII
91OQS788BE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NERVONIC ACID
DSC   WHO-DD  
Systematic Name English
(Z)-15-TETRACOSENOIC ACID
Systematic Name English
15-TETRACOSENOIC ACID, CIS-
Common Name English
TETRACOSENOIC ACID, (15Z)-
Common Name English
(15Z)-TETRACOSENOIC ACID
Common Name English
NEVONIC ACID
Common Name English
15-TETRACOSENOIC ACID, (Z)-
Common Name English
NERVONIC ACID [DSC]
Common Name English
CIS-15-TETRACOSENOIC ACID
Systematic Name English
SELACHOLEIC ACID
Common Name English
Nervonic acid [WHO-DD]
Common Name English
24:1(N-9)
Code English
NERVONIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
Classification Tree Code System Code
DSLD 3247 (Number of products:9)
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
NCI_THESAURUS C68423
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C68395
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY NCIT
SMS_ID
300000015660
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
CAS
506-37-6
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID80100930
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
CHEBI
44247
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
WIKIPEDIA
NERVONIC ACID
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
PUBCHEM
5281120
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
FDA UNII
91OQS788BE
Created by admin on Sat Dec 16 05:14:21 UTC 2023 , Edited by admin on Sat Dec 16 05:14:21 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT