Nervonic acid (CHEM022813)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:54:49 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022813
Identification
Common NameNervonic acid
ClassSmall Molecule
DescriptionA tetracosenoic acid having a cis-double bond at position 15.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-15-Tetracosenoic acidChEBI
(Z)-Tetracos-15-enoic acidChEBI
15cis-Tetracosenoic acidChEBI
cis-15-Tetracosenoic acidChEBI
cis-Delta(15)-Tetracosenoic acidChEBI
NervonsaeureChEBI
Selacholeic acidChEBI
(Z)-15-TetracosenoateGenerator
(Z)-Tetracos-15-enoateGenerator
15cis-TetracosenoateGenerator
cis-15-TetracosenoateGenerator
cis-delta(15)-TetracosenoateGenerator
cis-Δ(15)-tetracosenoateGenerator
cis-Δ(15)-tetracosenoic acidGenerator
SelacholeateGenerator
NervonateGenerator
(15Z)-Tetracos-15-enoateHMDB
(15Z)-Tetracos-15-enoic acidHMDB
(15Z)-TetracosenoateHMDB
(15Z)-Tetracosenoic 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
trans-Tetracos-15-enoic acidHMDB
(15Z)-15-Tetracosenoic acidHMDB
FA(24:1(15Z))HMDB
FA(24:1n9)HMDB
Nevonic acidHMDB
Nervonic acidChEBI
Chemical FormulaC24H46O2
Average Molecular Mass366.621 g/mol
Monoisotopic Mass366.350 g/mol
CAS Registry Number506-37-6
IUPAC Name(15Z)-tetracos-15-enoic acid
Traditional Namenervonic acid
SMILESCCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O
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-KTKRTIGZSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability49.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-969f119cba8683e5cc50Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-969f119cba8683e5cc50Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9782000000-97d131b02e4a98acfe12Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9551000000-d11282fde9bc72e71510Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0009000000-77254b7f9e0c5adec2c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05ur-9300000000-c24f47c8ec64393d34b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0api-9000000000-f9dc5919bdde58922d07Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0009000000-b5ce223be566232389ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-23437c970e4496314dc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0601-4529000000-0a095c0f2e7f69a7046cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9873000000-0479aea7f81e735a49b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-6bdffa41d37f32273117Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009000000-f28d20de75190fe2dfd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-2bdab238903303f33f49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-340806f152b23d48ad56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1009000000-ecb8e3e7292d693c5e2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9011000000-3a65628878739cc356f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-2009000000-966c9a99f927842d86e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l2-8349000000-44259b5853a420e306d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9100000000-3338b5c4d18e533bf611Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002368
FooDB IDFDB002934
Phenol Explorer IDNot Available
KNApSAcK IDC00001230
BiGG ID2218012
BioCyc IDNot Available
METLIN ID262
PDB IDNot Available
Wikipedia LinkNervonic acid
Chemspider ID4444565
ChEBI ID44247
PubChem Compound ID5281120
Kegg Compound IDC08323
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12742544
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16394593
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21147856
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8072429
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=9075193
6. 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.
7. 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.
8. 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.
9. 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.
10. Sargent JR, Coupland K, Wilson R: Nervonic acid and demyelinating disease. Med Hypotheses. 1994 Apr;42(4):237-42.
11. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.