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Record Information
Version3.6
Creation Date2006-05-22 14:17:50 UTC
Update Date2016-02-11 01:05:36 UTC
HMDB IDHMDB02368
Secondary Accession NumbersNone
Metabolite Identification
Common NameNervonic acid
DescriptionNervonic 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 ).
Structure
Thumb
Synonyms
ValueSource
(15Z)-Tetracosenoic acidChEBI
(Z)-15-Tetracosenoic acidChEBI
15cis-Tetracosenoic acidChEBI
cis-15-Tetracosenoic acidChEBI
cis-Delta(15)-Tetracosenoic acidChEBI
NervonsaeureChEBI
Selacholeic acidChEBI
(15Z)-TetracosenoateGenerator
(Z)-Tetracos-15-enoateGenerator
(Z)-15-TetracosenoateGenerator
15cis-TetracosenoateGenerator
cis-15-TetracosenoateGenerator
cis-delta(15)-TetracosenoateGenerator
cis-δ(15)-tetracosenoateGenerator
cis-δ(15)-tetracosenoic acidGenerator
SelacholeateGenerator
(15Z)-Tetracos-15-enoateHMDB
(15Z)-Tetracos-15-enoic acidHMDB
15-TetracosenoateHMDB
15-Tetracosenoic acidHMDB
15Z-TetracosenoateHMDB
15Z-Tetracosenoic acidHMDB
cis-15-TeracosenoateHMDB
cis-15-Teracosenoic acidHMDB
cis-15-TetracosenateHMDB
cis-15-Tetracosenic acidHMDB
cis-SelacholeateHMDB
cis-Selacholeic acidHMDB
NervonateHMDB
Chemical FormulaC24H46O2
Average Molecular Weight366.6208
Monoisotopic Molecular Weight366.349780716
IUPAC Name(15Z)-tetracos-15-enoic acid
Traditional Namenervonic acid
CAS Registry Number506-37-6
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O
InChI Identifier
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-
InChI KeyInChIKey=GWHCXVQVJPWHRF-KTKRTIGZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.77e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity115.01 m3·mol-1ChemAxon
Polarizability49.83 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-969f119cba8683e5cc50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0009000000-77254b7f9e0c5adec2c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05ur-9300000000-c24f47c8ec64393d34b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-f9dc5919bdde58922d07View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.070 +/- 0.006 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.900 +/- 0.974 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002934
KNApSAcK IDC00001230
Chemspider ID4444565
KEGG Compound IDC08323
BioCyc IDNot Available
BiGG ID2218012
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02368
Metagene LinkHMDB02368
METLIN ID262
PubChem Compound5281120
PDB IDNER
ChEBI ID44247
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bitsanis D, Crawford MA, Moodley T, Holmsen H, Ghebremeskel K, Djahanbakhch O: Arachidonic acid predominates in the membrane phosphoglycerides of the early and term human placenta. J Nutr. 2005 Nov;135(11):2566-71. [16251612 ]
  2. Laasonen M, Erkkila AT, Isotalo E, Maenpaa PK, Pulkkinen JJ, Virsu V, Haapanen ML: Serum lipid fatty acids and temporal processing acuity in children with oral clefts. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):263-70. Epub 2006 Mar 20. [16545557 ]
  3. Karlsson M, Marild S, Brandberg J, Lonn L, Friberg P, Strandvik B: Serum phospholipid fatty acids, adipose tissue, and metabolic markers in obese adolescents. Obesity (Silver Spring). 2006 Nov;14(11):1931-9. [17135608 ]
  4. Oda E, Hatada K, Kimura J, Aizawa Y, Thanikachalam PV, Watanabe K: Relationships between serum unsaturated fatty acids and coronary risk factors: negative relations between nervonic acid and obesity-related risk factors. Int Heart J. 2005 Nov;46(6):975-85. [16394593 ]
  5. Sargent JR, Coupland K, Wilson R: Nervonic acid and demyelinating disease. Med Hypotheses. 1994 Apr;42(4):237-42. [8072429 ]