Showing metabocard for Indoleacrylic acid (BMDB0000734)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:42 UTC
Update Date2020-04-22 15:05:03 UTC
BMDB IDBMDB0000734
Secondary Accession Numbers
  • BMDB00734
Metabolite Identification
Common NameIndoleacrylic acid
DescriptionIndoleacrylic acid, also known as 2-indoleacrylate, 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. Indoleacrylic acid is a weakly acidic compound (based on its pKa).
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 Weight187.1947
Monoisotopic Molecular Weight187.063328537
IUPAC Name(2E)-3-(1H-indol-2-yl)prop-2-enoic acid
Traditional Name(2E)-3-(1H-indol-2-yl)prop-2-enoic acid
CAS Registry Number1204-06-4
SMILES
OC(=O)\C=C\C1=CC2=C(N1)C=CC=C2
InChI Identifier
InChI=1S/C11H9NO2/c13-11(14)6-5-9-7-8-3-1-2-4-10(8)12-9/h1-7,12H,(H,13,14)/b6-5+
InChI KeySXOUIMVOMIGLHO-AATRIKPKSA-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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 - 186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1900000000-5bea0c7cc28fbf16cc9bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-8930000000-dd31397a073d8d298f0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-1e4da4a40a13dc3040ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02tc-0900000000-185cb8e2bf411f93c23fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9700000000-db32fca92b926fe968e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-f69f85afb3ba3821b065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0900000000-49227cba19b681b92792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-4900000000-c34f2b3621590f6fe3dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-04cbdafbbbb963000ee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-0900000000-89a52e5e9945e195469dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-dceb7d5d8c109f075486View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000734
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000938
KNApSAcK IDC00000111
Chemspider ID10607876
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5702
PubChem Compound15030923
PDB IDNot Available
ChEBI ID90333
References
Synthesis ReferenceMoffatt, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available