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Record Information
Version1.0
Creation Date2016-09-30 23:23:02 UTC
Update Date2020-05-21 16:28:27 UTC
BMDB IDBMDB0006528
Secondary Accession Numbers
  • BMDB06528
Metabolite Identification
Common NameClupanodonic acid
DescriptionDocosapentaenoic acid (22N-3), also known as DPA or 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 (22N-3) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Docosapentaenoic acid (22N-3) participates in a number of enzymatic reactions, within cattle. In particular, Docosapentaenoic acid (22N-3) can be biosynthesized from eicosapentaenoic acid through its interaction with the enzyme elongation OF very long chain fatty acids protein 5. In addition, Docosapentaenoic acid (22N-3) can be converted into tetracosapentaenoic acid (24:5N-3); which is catalyzed by the enzyme elongation OF very long chain fatty acids protein 4. In cattle, docosapentaenoic acid (22N-3) is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Docosapentaenoic acid (22N-3) has been found to be associated with the diseases known as colorectal cancer; also docosapentaenoic acid (22n-3) has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
Synonyms
ValueSource
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acidChEBI
(all Z)-7,10,13,16,19-Docosapentaenoic acidChEBI
all-cis-7,10,13,16,19-Docosapentaenoic acidChEBI
cis-7,10,13,16,19-Docosapentaenoic acidChEBI
Clupanodonic acidChEBI
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acidChEBI
Docosapentaenoic acidChEBI
DPAChEBI
DPAn-3ChEBI
7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acidKegg
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoateGenerator
(all Z)-7,10,13,16,19-DocosapentaenoateGenerator
all-cis-7,10,13,16,19-DocosapentaenoateGenerator
cis-7,10,13,16,19-DocosapentaenoateGenerator
ClupanodonateGenerator
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoateGenerator
DocosapentaenoateGenerator
7Z,10Z,13Z,16Z,19Z-DocosapentaenoateGenerator
Docosapentaenoate (22N-3)Generator
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoateHMDB
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acidHMDB
7,10,13,16,19-DocosapentaenoateHMDB
7,10,13,16,19-Docosapentaenoic acidHMDB
Docosapentaenoic acid, (all Z)-isomerHMDB
FA(22:5(7Z,10Z,13Z,16Z,19Z))HMDB
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acidHMDB
7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomerHMDB
Docosapentaenoic acid (C22:5 N3)HMDB
Osbond acidHMDB
(7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-Docosapentaenoic acidHMDB
(all-Z)-7,10,13,16,19-Docosapentaenoic acidHMDB
FA(22:5n3)HMDB
delta7,10,13,16,19-Docosapentaenoic acidHMDB
Omega3-docosapentaenoic acidHMDB
Δ7,10,13,16,19-docosapentaenoic acidHMDB
Ω3-docosapentaenoic acidHMDB
Chemical FormulaC22H34O2
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
IUPAC Name(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
Traditional Nameclupanodonic acid
CAS Registry Number24880-45-3
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(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/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyYUFFSWGQGVEMMI-JLNKQSITSA-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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.08ALOGPS
logP7.11ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.27 m³·mol⁻¹ChemAxon
Polarizability40.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5491000000-56de363323dabc6f26e3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9583000000-943203f8659c9ab3cac4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0090000000-260dcf8cd2e9cacf0e81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0090000000-b359128b4a9edc7dc9caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01x3-0492000000-89d3794a87bea421691bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-405cbfa338b34ddb7441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5793000000-59855762e7bce0a8ec9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avv-8970000000-49596865551dfe04eaa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-4d8832b1fd953fd8ec08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-1039000000-f6df0e4a8ec7c01d9955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-a69f7e9f82c75012f728View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified478.54 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified431.0989 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified1145.76 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified1381.37 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified1607.91 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified1982.67 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1028.732 +/- 423.595 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified877.448 +/- 302.568 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006528
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021831
KNApSAcK IDNot Available
Chemspider ID4593750
KEGG Compound IDC16513
BioCyc IDCPD-13792
BiGG ID2218032
Wikipedia LinkDocosapentaenoic acid
METLIN ID194
PubChem Compound5497182
PDB IDNot Available
ChEBI ID53488
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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.
  2. 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.

Enzymes

General function:
Not Available
Specific function:
Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:
ELOVL5
Uniprot ID:
Q2KJD9
Molecular weight:
35377.0
Reactions
Eicosapentaenoic acid → Clupanodonic aciddetails
Clupanodonic acid → Tetracosapentaenoic acid (24:5n-3)details