Nervonic acid

MUFA24:1Ω-9

  Overview

Stats

MUFA
Type
24
Carbons
1
Double bonds
0
Bis-allylic sites
366.6
Weight · g/mol
—
Melting point
C24H46O2
Formula

Also known as

IUPAC (Z)-tetracos-15-enoic acid

  At a Glance

Key Points

Named from the Latin for nerve; the monounsaturated analog of lignoceric acid, important in nerve myelin.

Source

Found in fish & seafood. Also made by the body.

Type

Very-long-chain monounsaturated fatty acid with 24 carbons and one cis double bond, an omega-9 fatty acid.

Identification

  Synonyms

Common Name Nervonic acid
IUPAC Name (Z)-tetracos-15-enoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia Nervonic_acid
Lipids
Lipid Maps LMFA01030092
Lipid Bank DFA0185
Swiss Lipids 000001131
PlantFA ID —
Food & Nutrition
FooDB FDB002934
INFOODS —
Chemistry / Compounds
PubChem CID 5281120
CAS 506-37-6
ChEBI 44247
ChEMBL CHEMBL1173379
ChemSpider 4444565
InChIKey —
ZINC ID ZINC000006920440
NIKKAJI ID J11.357C
PDBe NER
UCI (UniChem) 239961
SureChEMBL 21103
CCDC —
NMRShiftDB 60020620
Metabolites & Pathways
HMDB HMDB0002368
METLIN 262
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1140
BioCyc/MetaCyc —
MetaNetX ID MNXM6358
BiGG ID 2218012
KEGG C08323
KNApSAcK C00001230
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD018005
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code C68395
Regulatory
NIH UNII (USA) 91OQS788BE
FDA SRS (USA) 91OQS788BE
NHPID (Canada) —
DTXSID (USA) DTXSID801009308
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-939-503
eMolecules 532004
Mcule —
ChemicalBook CB5304545
MedChemExpress HY-N2526

Isomers of 24:1 (1)

Other fatty acids sharing the 24:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Nervonic acid
(Z)-tetracos-15-enoic acid
 15Z —
5281120
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Nervonic acid
Simple Notation 24:1
Notation 24:1(n-9)
IUPAC Name (Z)-tetracos-15-enoic acid
Structure:
Molecular C24H46O2
Structure CH3(CH2)7CH=CH(CH2)13COOH
SMILES CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O
Cis / Trans cis
E-Z 15Z
Physical:
Weight 366.6 g/mol
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 11
ATP Yield (Net) 160.5 ATP