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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2016-02-11 01:05:11 UTC
HMDB IDHMDB01976
Secondary Accession Numbers
  • 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. This compound belongs to the family of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain.
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
Docosapentaenoic acid (22N-6)ChEBI
(all-Z)-4,7,10,13,16-DocosapentaenoateGenerator
(4Z,7Z,10Z,13Z,16Z)-Docosa-4,7,10,13,16-pentaenoateGenerator
4Z,7Z,10Z,13Z,16Z-DocosapentaenoateGenerator
all-cis-Docosa-4,7,10,13,16-pentaenoateGenerator
Docosapentaenoate (22N-6)Generator
Docosa-4,7,10,13,16-pentaenoic acidHMDB
DocosapentaenoateHMDB
Docosapentaenoic acidHMDB
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 KeyInChIKey=AVKOENOBFIYBSA-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
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 Solubility0.000104 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.27 m3·mol-1ChemAxon
Polarizability40.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Adipose Tissue
  • Fibroblasts
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.4 +/- 5.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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. [14643447 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022774
KNApSAcK IDNot Available
Chemspider ID4945614
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDocosapentaenoic acid
NuGOwiki LinkHMDB01976
Metagene LinkHMDB01976
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. [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. [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. [10951510 ]
  4. Park Y, Harris W: EPA, but not DHA, decreases mean platelet volume in normal subjects. Lipids. 2002 Oct;37(10):941-6. [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. [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 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]