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Showing Compound Nervonic acid (FDB002934)

Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2019-11-26 02:58:11 UTC
Primary IDFDB002934
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNervonic acid
DescriptionPresent in fish and rape seed oils 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 (PMID: 16394593); 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. (PMID: 8072429); Nervonic acid is a monounsaturated omega-9 fatty acid. Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin. It is found in the sphingolipids of white matter in human brain.; Nervonic acid is used in the treatment of disorders involving demyelination, such as adrenoleukodystrophy and multiple sclerosis where there is a decreased level of nervonic acid in sphingolipids.
CAS Number506-37-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
NervonateGenerator
(15Z)-tetracos-15-enoatebiospider
(15Z)-tetracos-15-enoic acidbiospider
(15Z)-Tetracosenoatebiospider
(15Z)-Tetracosenoic acidbiospider
(Z)-15-Tetracosenoatebiospider
(z)-15-tetracosenoic acidbiospider
(Z)-Tetracos-15-enoateGenerator
(Z)-Tetracos-15-enoic acidChEBI
15-Tetracosenoatebiospider
15-Tetracosenoic acidbiospider
15cis-TetracosenoateGenerator
15cis-Tetracosenoic acidChEBI
15Z-tetracosenoatebiospider
15Z-tetracosenoic acidbiospider
cis-15-Teracosenoatebiospider
cis-15-Teracosenoic acidbiospider
cis-15-Tetracosenatebiospider
cis-15-Tetracosenic acidbiospider
cis-15-tetracosenoatebiospider
cis-15-tetracosenoic acidbiospider
cis-Delta(15)-tetracosenoatebiospider
cis-Delta(15)-tetracosenoic acidbiospider
Cis-selacholeatebiospider
Cis-selacholeic acidbiospider
cis-δ(15)-tetracosenoateGenerator
cis-δ(15)-tetracosenoic acidGenerator
Nervonic aciddb_source
NervonsaeureChEBI
Selacholeatebiospider
Selacholeic aciddb_source
tetracos-15-enoic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP9.45ALOGPS
logP9.45ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity115.01 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H46O2
IUPAC name(15E)-tetracos-15-enoic acid
InChI IdentifierInChI=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+
InChI KeyGWHCXVQVJPWHRF-MDZDMXLPSA-N
Isomeric SMILESCCCCCCCC\C=C\CCCCCCCCCCCCCC(O)=O
Average Molecular Weight366.6208
Monoisotopic Molecular Weight366.349780716
Classification
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 78.63%; H 12.65%; O 8.73%DFC
Melting PointMp 44-45°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge-1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444565
ChEMBL IDCHEMBL1173379
KEGG Compound IDC08323
Pubchem Compound ID5281120
Pubchem Substance IDNot Available
ChEBI ID7526
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02368
CRC / DFC (Dictionary of Food Compounds) IDCPK11-W:CPK15-A
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2218012
KNApSAcK IDC00001230
HET IDNER
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNervonic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.