Docosapentaenoic acid (22n-6) (CHEM021857)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:10 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021857
Identification
Common NameDocosapentaenoic acid (22n-6)
ClassSmall Molecule
DescriptionThe all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 4-, 7-, 10-, 13- and 16-positions. It is a member of n-6 PUFA and a product of linoleic acid metabolism.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
DPAn-6ChEBI
(all-Z)-4,7,10,13,16-DocosapentaenoateGenerator
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
Osbond acidHMDB
FA(22:5(4Z,7Z,10Z,13Z,16Z))HMDB
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acidHMDB
Docosapentaenoic acid (C22:5 N6)HMDB
Docosapentaenoic acid, (all Z)-isomerHMDB
Docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomerHMDB
(4Z,7Z,10Z,13Z,16Z)-4,7,10,13,16-Docosapentaenoic acidHMDB
DPAHMDB
FA(22:5n6)HMDB
Chemical FormulaC22H34O2
Average Molecular Mass330.504 g/mol
Monoisotopic Mass330.256 g/mol
CAS Registry Number25448-00-4
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
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-7490000000-97ad3e356a5f908f9003Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9244000000-8e631b61a994e509b114Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0139000000-31a18234c1c393f0a6a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4592000000-fa33f23033ae64b97560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-7960000000-ccf21f4fdb0af5b5c619Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-fa512c1688ce00ffd41dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1059000000-8f65bcb90bc078a7912dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-4ded7c8842575d2752c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f4bd181f937819513660Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1019000000-a6b85cd3220846053c5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9041000000-f6b90f282a7eccd547fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1239000000-b1d4cd921a69d9f8653fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-6933000000-1d63fd3f377179dddb82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9800000000-eeb640c3008512e3c40aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001976
FooDB IDFDB022774
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6412
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4945614
ChEBI ID65136
PubChem Compound ID6441454
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14643447
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17291553
3. 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.
4. 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.
5. Park Y, Harris W: EPA, but not DHA, decreases mean platelet volume in normal subjects. Lipids. 2002 Oct;37(10):941-6.
6. 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.
7. 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.
8. 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.
9. 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.