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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 14:34:40 UTC
Update Date2018-05-20 19:09:50 UTC
HMDB IDHMDB0006528
Secondary Accession Numbers
  • HMDB06528
Metabolite Identification
Common NameDocosapentaenoic acid (22n-3)
DescriptionDocosapentaenoic acid (22n-3) (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source of this metabolite. There are three functions of docosapentaenoic acid. Most importantly, it is a component of phospholipids found in all animal cell membranes, and a deficiency of docosapentaenoic acid leads to faulty membranes being formed. Secondly, it is involved in the transport and oxidation of cholesterol, and clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes. Outcomes include sudden failure of growth, lesions of the skin, kidney, and connective tissue, erythrocyte fragility, impaired fertility, and the uncoupling of oxidation and phosphorylation. In humans, pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common in Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension, and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid (PMID: 6469703 ).
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-7C,10C,13C,16C,19C-pentaensaeureChEBI
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acidChEBI
DPAChEBI
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoateGenerator
DocosapentaenoateGenerator
(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
(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
4,7,10,13,16-Docosapentaenoic acidMeSH
Docosa-4,7,10,13,16-pentaenoic acidMeSH
Docosa-4,7,10,13,16-pentaenoic acid 5-(14)C-labeled CPD, (all-Z)-isomerMeSH
Docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomerMeSH
Docosapentaenoic acid, (all Z)-isomerMeSH
DPAn-3HMDB
FA(22:5(7Z,10Z,13Z,16Z,19Z))HMDB
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified39.334 +/- 6.0514 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified36.308 +/- 6.0514 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified33.282 +/- 6.0514 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified30.257 +/- 9.0770 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified45.779 +/- 12.768 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified48.925 +/- 11.256 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified60 +/- 20 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.993 +/- 0.46 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified60 +/- 20 uMAdult (>18 years old)MaleNormal details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.400 +/- 0.005 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified9.0 (7.3-11.5) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified34.8 +/- 12.2 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.386 +/- 0.229 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified18.7 +/- 10.4 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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. Sinclair HM: Essential fatty acids in perspective. Hum Nutr Clin Nutr. 1984 Jul;38(4):245-60. [PubMed:6469703 ]