Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2015-10-09 22:31:45 UTC
Primary IDFDB002927
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEicosanoic acid
DescriptionConstit. of arachis (Arachis hypogaea) (ground-nut) oil glycerides Arachidic acid also called eicosanoic acid is a saturated fatty acid found in peanut oil. It can be formed by the hydrogenation of arachidonic acid. It is practically insoluble in water and stable under ordinary conditions (Wikipedia)
CAS Number506-30-9
Structure
Thumb
Synonyms
SynonymSource
Arachatebiospider
Arachic aciddb_source
Arachidatebiospider
Arachidic aciddb_source
ArachidinateGenerator
Arachidinic acidbiospider
ArachinsaeureChEBI
CH3-[CH2]18-COOHChEBI
Eicosanoatebiospider
EicosoateGenerator
Eicosoic acidbiospider
Icosanoatebiospider
Icosanoic aciddb_source
N-Eicosanoatebiospider
N-Eicosanoic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility5.0e-05 g/LALOGPS
logP8.53ALOGPS
logP8.03ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity95.49 m³·mol⁻¹ChemAxon
Polarizability42.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H40O2
IUPAC nameicosanoic acid
InChI IdentifierInChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)
InChI KeyInChIKey=VKOBVWXKNCXXDE-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight313
Monoisotopic Molecular Weight312
Classification
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp 77°DFC
Boiling PointBp1 203-205°DFC
Experimental Water SolubilityNot Available
Experimental logP9.29SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0900000000-cc7f30812c4ef45583b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2901000000-7d146c5d993118307ce5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0596-9100000000-53a544b7fbf2ee3b176aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-cc7f30812c4ef45583b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2901000000-7d146c5d993118307ce5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1900000000-33733dae76fd89dc7394View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-ff95bd6be578f2c72ce9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9560000000-d2d19ad6d5ef54fdf90aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0029000000-273e657da59fa67385c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9200000000-84b07a6d22109c441336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9100000000-9d6e321e2bf8cd1f20e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0009000000-d7e3408b3b2e854229b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0109000000-c0ed9d28e54855b40069View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0013493000-832a78a9cf97d74660eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06vi-0012391000-e4dcf31aba99059fcf39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0193000000-031626259c4a17016165View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0091000000-9389b44ea9cfe1afe40bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-9100000000-091619221e36a7a177ffView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10035
ChEMBL IDCHEMBL1173381
KEGG Compound IDC06425
Pubchem Compound ID10467
Pubchem Substance IDNot Available
ChEBI ID28822
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02212
CRC / DFC (Dictionary of Food Compounds) IDCPG46-Q:CPG46-Q
EAFUS IDNot Available
Dr. Duke IDARACHIC-ACID|ARACHIDIC-ACID|EICOSANOIC-ACID
BIGG ID48230
KNApSAcK IDC00001209
HET IDDCR
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArachidic 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
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Liver carboxylesterase 1CES1P23141
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
CholinesteraseBCHEP06276
Carboxylesterase 5ACES5AQ6NT32
60 kDa lysophospholipaseASPGQ86U10
Fatty acid synthaseFASNP49327
Galactoside-binding soluble lectin 13LGALS13Q9UHV8
Eosinophil lysophospholipaseCLCQ05315
Cocaine esteraseCES2O00748
Acylphosphatase-2ACYP2P14621
Acylphosphatase-1ACYP1P07311
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
Acid ceramidaseASAH1Q13510
Homeodomain-interacting protein kinase 1HIPK1Q86Z02
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 6SLC27A6Q9Y2P4
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Neuropathy target esterasePNPLA6Q8IY17
Carboxylesterase 3CES3Q6UWW8
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
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).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.