(all-Z)-13,16,19-Docosatrienoic acid (CHEM032857)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:45:04 UTC
Update Date2016-11-09 01:20:48 UTC
Accession NumberCHEM032857
Identification
Common Name(all-Z)-13,16,19-Docosatrienoic acid
ClassSmall Molecule
DescriptionA long-chain omega-3 fatty acid that is docosanoic acid having three double bonds located at positions 13, 16 and 19 (the (13Z,16Z,19Z-geoisomer).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13Z,16Z,19Z) Docosatrienoic acidChEBI
all-cis-13,16,19 Docosatrienoic acidChEBI
(13Z,16Z,19Z) DocosatrienoateGenerator
all-cis-13,16,19 DocosatrienoateGenerator
DocosatrienoateGenerator
13,16,19-DocosatrienoateHMDB
13,16,19-Docosatrienoic acidHMDB
(13Z,16Z,19Z)-DocosatrienoateHMDB
(13Z,16Z,19Z)-13,16,19-Docosatrienoic acidHMDB
FA(22:3(13Z,16Z,19Z))HMDB
FA(22:3n3)HMDB
cis-13,cis-16,cis-19-Docosatrienoic acidHMDB
Docosatrienoic acidHMDB
Chemical FormulaC22H38O2
Average Molecular Mass334.536 g/mol
Monoisotopic Mass334.287 g/mol
CAS Registry Number28845-86-5
IUPAC Name(13Z,16Z,19Z)-docosa-13,16,19-trienoic acid
Traditional NameDTrE
SMILESCC\C=C\C\C=C/C\C=C\CCCCCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C22H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10H,2,5,8,11-21H2,1H3,(H,23,24)/b4-3+,7-6-,10-9+
InChI KeyWBBQTNCISCKUMU-BXPSWRNBSA-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 Solubility3.4e-05 g/LALOGPS
logP7.92ALOGPS
logP7.84ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity108.04 m³·mol⁻¹ChemAxon
Polarizability43.33 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, Positivesplash10-0007-4951000000-1aad4863d2ec911cb7a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9883000000-0f3500426715a9c51ccfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0029000000-12563c9311c272b03ef4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-5493000000-291ecbb14a0d724890cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06g3-9860000000-e96804bc997c3b08d694Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-12025f680802c5b83784Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-1039000000-e7477e45366329874498Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-a8051c16fa686909e011Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-31a1efc0c1d4ea277a4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1009000000-836d44588c0b993abebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9111000000-eb033fb8799e55aec4f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3339000000-ba30b08961f96e0795e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067i-9734000000-250c3c0d8fa667dd1b8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-0b8ac85be8fec95c7ff1Spectrum
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 IDHMDB0002823
FooDB IDFDB112372
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID195
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4471982
ChEBI ID77807
PubChem Compound ID5312557
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=10712534
2. Soares MC, Alessio ML, Leger CL, Bluet-Pajot MT, Clauser H, Enjalbert A, Kordon C, Wandscheer DE: Effect of essential fatty acid deficiency on membrane fatty acid content and growth hormone stimulation of rat pituitaries during postnatal development. J Lipid Res. 1995 Jun;36(6):1401-6.
3. Krutetskaia ZI, Lebedev OE, Roshchina NG, Butov SN: [The effect of docosatrienoic acid on the potassium channels of outward rectification in the membrane of rat peritoneal macrophages]. Fiziol Zh Im I M Sechenova. 1995 Jul;81(7):111-9.
4. 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.