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Human Metabolome Database Version 3.5

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Showing metabocard for Nervonic acid (HMDB02368)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:50 -0600
Update Date 2013-02-08 17:11:49 -0700
HMDB ID HMDB02368
Secondary Accession Numbers None
Metabolite Identification
Common Name Nervonic acid
Description 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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (15Z)-tetracos-15-enoate
  2. (15Z)-tetracos-15-enoic acid
  3. (15Z)-Tetracosenoate
  4. (15Z)-Tetracosenoic acid
  5. (Z)-15-Tetracosenoate
  6. (Z)-15-Tetracosenoic acid
  7. 15-Tetracosenoate
  8. 15-Tetracosenoic acid
  9. 15Z-Tetracosenoate
  10. 15Z-Tetracosenoic acid
  11. cis-15-Teracosenoate
  12. cis-15-Teracosenoic acid
  13. cis-15-Tetracosenate
  14. cis-15-Tetracosenic acid
  15. cis-15-Tetracosenoate
  16. cis-15-Tetracosenoic acid
  17. cis-delta(15)-Tetracosenoate
  18. cis-delta(15)-Tetracosenoic acid
  19. cis-Selacholeate
  20. cis-Selacholeic acid
  21. Nervonate
  22. Selacholeate
  23. Selacholeic acid
Chemical Formula C24H46O2
Average Molecular Weight 366.6208
Monoisotopic Molecular Weight 366.349780716
IUPAC Name (15Z)-tetracos-15-enoic acid
Traditional IUPAC Name nervonic acid
CAS Registry Number 506-37-6
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 Key GWHCXVQVJPWHRF-KTKRTIGZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated fatty acids(Lipidmaps)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.770E-05 g/L ALOGPS
LogP 9.45 ALOGPS
LogP 9.45 ChemAxon
LogS -7.32 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 115.01 ChemAxon
Polarizability 49.83 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.070 +/- 0.006 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.900 +/- 0.974 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002934
KNApSAcK ID C00001230 Link_out
Chemspider ID 4444565 Link_out
KEGG Compound ID C08323 Link_out
BioCyc ID Not Available
BiGG ID 2218012 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB02368 Link_out
Metagene Link HMDB02368 Link_out
METLIN ID 262 Link_out
PubChem Compound 5281120 Link_out
PDB ID NER Link_out
ChEBI ID 44247 Link_out
References
Synthesis Reference Not 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. Pubmed: 16251612 Link_out
  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. Pubmed: 16545557 Link_out
  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. Pubmed: 17135608 Link_out
  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. Pubmed: 16394593 Link_out