3-(1H-Indol-3-yl)-2-propenoic acid (CHEM023394)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:01:37 UTC
Update Date2016-11-09 01:17:42 UTC
Accession NumberCHEM023394
Identification
Common Name3-(1H-Indol-3-yl)-2-propenoic acid
ClassSmall Molecule
DescriptionAn alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which one of the hydrogens at position 3 is replaced by an indol-2-yl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Indoleacrylic acidChEBI
2-Indolylacrylic acidChEBI
3-(2-Indolyl)acrylic acidChEBI
Indole-2-acrylic acidChEBI
trans-2-Indoleacrylic acidChEBI
2-IndoleacrylateGenerator
2-IndolylacrylateGenerator
3-(2-Indolyl)acrylateGenerator
Indole-2-acrylateGenerator
trans-2-IndoleacrylateGenerator
IndoleacrylateGenerator
(e)-3-(indol-2-yl)AcrylateHMDB
3-IndoleacrylateHMDB
3-Indoleacrylic acidHMDB
Indoleacrylic acidChEBI
Chemical FormulaC11H9NO2
Average Molecular Mass187.195 g/mol
Monoisotopic Mass187.063 g/mol
CAS Registry Number1204-06-4
IUPAC Name(2E)-3-(1H-indol-2-yl)prop-2-enoic acid
Traditional Name(2E)-3-(1H-indol-2-yl)prop-2-enoic acid
SMILESOC(=O)\C=C/C1=CNC2=C1C=CC=C2
InChI IdentifierInChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5-
InChI KeyPLVPPLCLBIEYEA-WAYWQWQTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.22 g/LALOGPS
logP2.3ALOGPS
logP2.15ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.02 m³·mol⁻¹ChemAxon
Polarizability19.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1900000000-5bea0c7cc28fbf16cc9bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-8930000000-dd31397a073d8d298f0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-1e4da4a40a13dc3040ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02tc-0900000000-185cb8e2bf411f93c23fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9700000000-db32fca92b926fe968e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-f69f85afb3ba3821b065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0900000000-49227cba19b681b92792Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-4900000000-c34f2b3621590f6fe3dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-04cbdafbbbb963000ee9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-0900000000-89a52e5e9945e195469dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-dceb7d5d8c109f075486Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000734
FooDB IDFDB000938
Phenol Explorer IDNot Available
KNApSAcK IDC00000111
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5702
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10607876
ChEBI ID90333
PubChem Compound ID15030923
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Moffatt, J. S. Preparation of b-3-indolylacrylic acid. Journal of the Chemical Society (1957), 1442-3.; Bauguess, Lyle C.; Berg, Clarence P. The availability of indole derivatives for supplementing diets deficient in tryptophan. Proceedings of the Iowa Academy of Science (1933), 40 110-11.
2. Moffatt, J. S. Preparation of b-3-indolylacrylic acid. Journal of the Chemical Society (1957), 1442-3.; Bauguess, Lyle C.; Berg, Clarence P. The availability of indole derivatives for supplementing diets deficient in tryptophan. Proceedings of the Iowa Academy of Science (1933), 40 110-11.
3. Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13.
4. Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007.
5. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22.