Showing metabocard for Docosapentaenoic acid (BMDB0001976)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:25 UTC
Update Date2020-06-04 20:33:27 UTC
MCDB ID BMDB0001976
Secondary Accession Numbers
  • BMDB01976
Metabolite Identification
Common NameDocosapentaenoic acid
DescriptionDocosapentaenoic acid, also known as docosapentaenoate, 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. Docosapentaenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, docosapentaenoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DocosapentaenoateGenerator
Chemical FormulaC22H34O2
Average Molecular Weight330.512
Monoisotopic Molecular Weight330.255880335
IUPAC Name(2E,4E,6E,8E,10E)-docosa-2,4,6,8,10-pentaenoic acid
Traditional Namedocosapentaenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCCCCC)=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])C(O)=O
InChI Identifier
InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h12-21H,2-11H2,1H3,(H,23,24)/b13-12+,15-14+,17-16+,19-18+,21-20+
InChI KeyYEKFYCQGYMVFKR-MBFZXKRTSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.8ALOGPS
logP7.47ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.25 m³·mol⁻¹ChemAxon
Polarizability43.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-f33cfd84bc3dfc9f79982019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0309-1392000000-eb49857efdd04a418d992019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l06-6790000000-8e45fb020404d27be1252019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-d267755337df97df4ea12019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0039000000-179a79763d44df72e5f82019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rx-9372000000-c7ed30d5c278c92f92f52019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2390 +/- 575 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2269 +/- 484 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDocosapentaenoic acid
METLIN IDNot Available
PubChem Compound6438348
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  3. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.