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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 14:34:40 UTC
Update Date2022-03-07 02:49:32 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
Data?1582752389
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
7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomerMeSH
Docosapentaenoic acid (C22:5 N3)MeSH
Osbond acidMeSH
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acidMeSH
7,10,13,16,19-Docosapentaenoic acidMeSH
Docosapentaenoic acid, (all Z)-isomerMeSH
(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
FA(22:5(7Z,10Z,13Z,16Z,19Z))HMDB
(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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.51631661259
DarkChem[M-H]-190.66331661259
DeepCCS[M+H]+188.9530932474
DeepCCS[M-H]-186.59230932474
DeepCCS[M-2H]-219.47830932474
DeepCCS[M+Na]+195.04330932474
AllCCS[M+H]+190.032859911
AllCCS[M+H-H2O]+187.232859911
AllCCS[M+NH4]+192.732859911
AllCCS[M+Na]+193.432859911
AllCCS[M-H]-189.632859911
AllCCS[M+Na-2H]-191.732859911
AllCCS[M+HCOO]-194.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Docosapentaenoic acid (22n-3)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O3993.9Standard polar33892256
Docosapentaenoic acid (22n-3)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O2283.2Standard non polar33892256
Docosapentaenoic acid (22n-3)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O2524.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosapentaenoic acid (22n-3),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C2559.7Semi standard non polar33892256
Docosapentaenoic acid (22n-3),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C2808.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-3) GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5491000000-56de363323dabc6f26e32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-3) GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9583000000-943203f8659c9ab3cac42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-3) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) LC-ESI-IT , negative-QTOFsplash10-000i-0090000000-260dcf8cd2e9cacf0e812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) Linear Ion Trap , negative-QTOFsplash10-000i-0090000000-b359128b4a9edc7dc9ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) Linear Ion Trap , positive-QTOFsplash10-01x3-0492000000-89d3794a87bea421691b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Positive-QTOFsplash10-03di-0039000000-405cbfa338b34ddb74412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Positive-QTOFsplash10-000i-5793000000-59855762e7bce0a8ec9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Positive-QTOFsplash10-0avv-8970000000-49596865551dfe04eaa12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Negative-QTOFsplash10-004i-0019000000-4d8832b1fd953fd8ec082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Negative-QTOFsplash10-01ti-1039000000-f6df0e4a8ec7c01d99552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Negative-QTOFsplash10-0a4l-9130000000-a69f7e9f82c75012f7282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Negative-QTOFsplash10-004i-0009000000-f4bd181f9378195136602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Negative-QTOFsplash10-01t9-1009000000-fd8104aee9b78a72f4db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Negative-QTOFsplash10-0006-9221000000-a71d2d6e07928441d5ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Positive-QTOFsplash10-01q9-2329000000-918ad0c35d9079c18ee12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Positive-QTOFsplash10-001i-4911000000-cca43fd70d0980b4845e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Positive-QTOFsplash10-001i-9700000000-ca068d510d72f2bb000e2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
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 QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>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 but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021831
KNApSAcK IDC00052249
Chemspider ID4593750
KEGG Compound IDC16513
BioCyc IDCPD-13792
BiGG ID2218032
Wikipedia LinkDocosapentaenoic acid
METLIN ID194
PubChem Compound5497182
PDB IDNot Available
ChEBI ID53488
Food Biomarker OntologyNot Available
VMH IDCLPND
MarkerDB IDMDB00000486
Good Scents IDNot Available
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 ]
  2. 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. [PubMed:32033212 ]