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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002823
Secondary Accession Numbers
  • HMDB02823
Metabolite Identification
Common NameDocosatrienoic acid
DescriptionDocosatrienoic acid, also known as docosatrienoate, 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. Docosatrienoic acid is a very hydrophobic molecule, is practically insoluble (in water), and is relatively neutral. Application of docosatrienoic acid was shown to dose-dependently decrease the peak K+ current amplitude and accelerate the potassium activation and inactivation kinetics at all membrane potentials.
Structure
Data?1582752257
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 Weight334.5359
Monoisotopic Molecular Weight334.28718046
IUPAC Name(13Z,16Z,19Z)-docosa-13,16,19-trienoic acid
Traditional NameDTrE
CAS Registry Number28845-86-5
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=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-PDBXOOCHSA-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.6431661259
DarkChem[M-H]-191.88731661259
DeepCCS[M+H]+190.02630932474
DeepCCS[M-H]-187.66830932474
DeepCCS[M-2H]-220.55530932474
DeepCCS[M+Na]+196.11930932474
AllCCS[M+H]+193.432859911
AllCCS[M+H-H2O]+190.732859911
AllCCS[M+NH4]+195.932859911
AllCCS[M+Na]+196.632859911
AllCCS[M-H]-193.032859911
AllCCS[M+Na-2H]-195.332859911
AllCCS[M+HCOO]-198.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Docosatrienoic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O3761.1Standard polar33892256
Docosatrienoic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O2416.7Standard non polar33892256
Docosatrienoic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O2555.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosatrienoic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C2610.6Semi standard non polar33892256
Docosatrienoic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2861.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-4951000000-1aad4863d2ec911cb7a82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosatrienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9883000000-0f3500426715a9c51ccf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosatrienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosatrienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Positive-QTOFsplash10-014r-0029000000-12563c9311c272b03ef42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Positive-QTOFsplash10-00n0-5493000000-291ecbb14a0d724890cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Positive-QTOFsplash10-06g3-9860000000-e96804bc997c3b08d6942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Negative-QTOFsplash10-001i-0019000000-12025f680802c5b837842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Negative-QTOFsplash10-00m0-1039000000-e7477e453663298744982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Negative-QTOFsplash10-052f-9130000000-a8051c16fa686909e0112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Negative-QTOFsplash10-001i-0009000000-31a1efc0c1d4ea277a4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Negative-QTOFsplash10-00lr-1009000000-836d44588c0b993abebf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Negative-QTOFsplash10-0006-9111000000-eb033fb8799e55aec4f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Positive-QTOFsplash10-00kr-3339000000-ba30b08961f96e0795e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Positive-QTOFsplash10-067i-9734000000-250c3c0d8fa667dd1b8c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Positive-QTOFsplash10-05po-9200000000-0b8ac85be8fec95c7ff12021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.004 +/- 0.001 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112372
KNApSAcK IDNot Available
Chemspider ID4471982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID195
PubChem Compound5312557
PDB IDNot Available
ChEBI ID77807
Food Biomarker OntologyNot Available
VMH IDM00341
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:7666016 ]
  2. 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. [PubMed:8714386 ]
  3. 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. [PubMed:32033212 ]