We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Human Metabolome Database Version 2.5

 

Showing metabocard for Docosapentaenoic acid (HMDB06528)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2007-05-23 15:34:40
Update Date 2011-08-18 18:23:10
Accession Number HMDB06528
Secondary Accession Numbers Not Available
Common Name Docosapentaenoic acid
Description Docosapentaenoic acid (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. There are three functions of docosapentaenoic acid. The most important is as part of phospholipids in all animal cellular membranes: a deficiency of docosapentaenoic acid leads to faulty membranes being formed. A second is in the transport and oxidation of cholesterol: 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: sudden failure of growth, lesions of skin and kidney and connective tissue, erythrocyte fragility, impaired fertility, uncoupling of oxidation and phosphorylation. In man 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 on 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)
Synonyms
  1. Clupanodonic acid
  2. (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid
  3. Docosapentaenoic acid
  4. DPA
  5. (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate
  6. Docosapentaenoate
  7. Clupanodonate
  8. 7,10,13,16,19-docosapentaenoic acid
  9. 7,10,13,16,19-docosapentaenoate
Chemical IUPAC Name (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
Chemical Formula C22H34O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Fatty Acids
Sub Class
  • Long chain fatty acids
Family
  • Mammalian Metabolite
Species
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 330.504
Monoisotopic Molecular Weight 330.255890
Isomeric SMILES CCC=C/CC=C/CC=C/CC=C/CC=C/CCCCCC(O)=O
Canonical SMILES CCC=CCC=CCC=CCC=CCC=CCCCCCC(O)=O
KEGG Compound ID C16513 Link Image
BioCyc ID Not Available
BiGG ID 2218032 Link Image
Wikipedia Link clupanodonic acid Link Image
NuGOwiki Link HMDB06528 Link Image
Metagene Link HMDB06528 Link Image
METLIN ID 194 Link Image
PubChem Compound 5497182 Link Image
PubChem Substance 47959475 Link Image
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/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-
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.18e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.1 [Predicted by PubChem via XLOGP]; 7.08 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 9.0 (7.3-11.5) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geerling BJ, v Houwelingen AC, Badart-Smook A, Stockbrugger RW, Brummer RJ: Fat intake and fatty acid profile in plasma phospholipids and adipose tissue in patients with Crohn's disease, compared with controls. Am J Gastroenterol. 1999 Feb;94(2):410-7. [PubMed Link Image]
Biofluid Blood
Value 0.386 +/- 0.229 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. [PubMed Link Image]
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
Biofluid Blood
Value 0.400 +/- 0.005 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. Epub 2010 Jul 29. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 Link Image map00592 Link Image
General References
  1. Wikipedia Link Image