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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2018-05-20 09:56:13 UTC
HMDB IDHMDB0001976
Secondary Accession Numbers
  • HMDB0060113
  • HMDB01976
  • HMDB60113
Metabolite Identification
Common NameDocosapentaenoic acid (22n-6)
DescriptionDocosapentaenoic acid is an unsaturated fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans. Docosapentaenoic acid (22n-6) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Docosapentaenoic acid (22n-6) can be found in blood and urine, as well as in human adipose tissue, fibroblasts, and platelet tissues. Within the cell, docosapentaenoic acid (22n-6) is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. In humans, docosapentaenoic acid (22n-6) is involved in alpha-linolenic acid and linoleic acid metabolism. Docosapentaenoic acid (22n-6) is found to be associated with thyroid cancer.
Structure
Thumb
Synonyms
ValueSource
(all-Z)-4,7,10,13,16-Docosapentaenoic acidChEBI
22:5(4Z,7Z,10Z,13Z,16Z)ChEBI
4Z,7Z,10Z,13Z,16Z-Docosapentaenoic acidChEBI
all-cis-Docosa-4,7,10,13,16-pentaenoic acidChEBI
C22:5N-6,9,12,15,18ChEBI
(all-Z)-4,7,10,13,16-DocosapentaenoateGenerator
Docosapentaenoate (22N-6)Generator
4Z,7Z,10Z,13Z,16Z-DocosapentaenoateGenerator
all-cis-Docosa-4,7,10,13,16-pentaenoateGenerator
Docosa-4,7,10,13,16-pentaenoic acidHMDB
DocosapentaenoateHMDB
Docosapentaenoic acidHMDB
Osbond acidHMDB
DPAn-6HMDB
FA(22:5(4Z,7Z,10Z,13Z,16Z))HMDB
Chemical FormulaC22H34O2
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
IUPAC Name(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
Traditional Name(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
CAS Registry Number25448-00-4
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(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/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyAVKOENOBFIYBSA-WMPRHZDHSA-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
Physiological effect

Health effect:

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 Solubility0.0001 g/LALOGPS
logP7.18ALOGPS
logP7.11ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.27 m³·mol⁻¹ChemAxon
Polarizability40.58 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, Positivesplash10-00fu-7490000000-97ad3e356a5f908f9003View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9244000000-8e631b61a994e509b114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0139000000-31a18234c1c393f0a6a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4592000000-fa33f23033ae64b97560View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-7960000000-ccf21f4fdb0af5b5c619View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-fa512c1688ce00ffd41dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1059000000-8f65bcb90bc078a7912dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-4ded7c8842575d2752c5View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 +/- 4.1 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.4 +/- 5.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.9 +/- 5.2 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
UrineDetected and Quantified3.0 +/- 2.3 umol/mmol creatinineAdult (>18 years old)Both
Thyroid cancer
details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Colorectal cancer
  1. 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 ]
  2. 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 IDFDB022774
KNApSAcK IDNot Available
Chemspider ID4945614
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6412
PubChem Compound6441454
PDB IDNot Available
ChEBI ID65136
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
  2. Marckmann P, Lassen A, Haraldsdottir J, Sandstrom B: Biomarkers of habitual fish intake in adipose tissue. Am J Clin Nutr. 1995 Nov;62(5):956-9. [PubMed:7572741 ]
  3. Pedersen JI, Ringstad J, Almendingen K, Haugen TS, Stensvold I, Thelle DS: Adipose tissue fatty acids and risk of myocardial infarction--a case-control study. Eur J Clin Nutr. 2000 Aug;54(8):618-25. [PubMed:10951510 ]
  4. Park Y, Harris W: EPA, but not DHA, decreases mean platelet volume in normal subjects. Lipids. 2002 Oct;37(10):941-6. [PubMed:12530552 ]
  5. Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33. [PubMed:12499346 ]
  6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]