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1H-Indole-3-acetamide (FDB000937)

Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2020-02-24 19:10:17 UTC
Primary IDFDB000937
Secondary Accession Numbers
  • FDB030919
Chemical Information
FooDB Name1H-Indole-3-acetamide
DescriptionIndole-3-acetamide, also known as auxin amide, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-acetamide has been detected, but not quantified in, several different foods, such as plains prickly pears (Opuntia macrorhiza), wakames (Undaria pinnatifida), wax apples (Eugenia javanica), garden onions (Allium cepa), and custard apples (Annona reticulata). This could make indole-3-acetamide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Indole-3-acetamide.
CAS Number879-37-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP1.17ALOGPS
logP0.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.94ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.88 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.27 m³·mol⁻¹ChemAxon
Polarizability18.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10N2O
IUPAC name2-(1H-indol-3-yl)acetamide
InChI IdentifierInChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
InChI KeyZOAMBXDOGPRZLP-UHFFFAOYSA-N
Isomeric SMILESNC(=O)CC1=CNC2=CC=CC=C12
Average Molecular Weight174.1992
Monoisotopic Molecular Weight174.079312952
Classification
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.95%; H 5.79%; N 16.08%; O 9.18%DFC
Melting PointMp 150-151°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-6404e04bc67c64bf01fe2015-03-01View Spectrum
GC-MS1H-Indole-3-acetamide, 3 TMS, GC-MS Spectrumsplash10-000i-1940000000-2e0b818a401b68b37cb0Spectrum
GC-MS1H-Indole-3-acetamide, 2 TMS, GC-MS Spectrumsplash10-0udi-1690000000-bd0b44e69af5595426d5Spectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-000i-1940000000-2e0b818a401b68b37cb0Spectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-0udi-1690000000-bd0b44e69af5595426d5Spectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-0udi-0690000000-7d97254bac7f634f8ef6Spectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-0006-0790000000-3baf5bdb295590ef5e30Spectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-014i-0490000000-68d3c7497fdc144df3ffSpectrum
GC-MS1H-Indole-3-acetamide, non-derivatized, GC-MS Spectrumsplash10-014i-0962600000-44dab9af3d483d324860Spectrum
Predicted GC-MS1H-Indole-3-acetamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1900000000-bee6d4f863595e61f64cSpectrum
Predicted GC-MS1H-Indole-3-acetamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-8e500497980b176c3b932017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0089-0900000000-7ed0e1427315880135e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-fc7d0772d90e4729aef22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-3900000000-f1a9ae54e7b833bbf7262017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9500000000-1c040087111497793e632017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00e9-0900000000-9f05f0a7e9fe3835ecf32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-67ccc2768cce859f24992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00e9-0900000000-40c799aeb47a282dda9e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-94ea4a1c3d4e34debac92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-c5a3e3d2da08ed3d6ab92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-269e12170dc5be0e70732021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-c1b8fc03b1893c6c77322021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-4900000000-8071bee81ef6d0157bee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0900000000-0f6021a437dc4ae1d5892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0900000000-2781bfef6ced20d656662021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0900000000-5de87672862d9a87ffad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a7211114eee7d20849642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-3de8c91d628d34d622902021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0900000000-1f155ed0ed5f83f867252015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0900000000-07eabe3745639209f1332015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-b726329bdc2f6e86c3312015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a3d953ff50b9cf8574732015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ec-2900000000-945fb87e55e153b511602015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-8838f76ce5faa9a043372015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-10871b30e21061e9ad032021-09-21View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID386
ChEMBL IDNot Available
KEGG Compound IDC02693
Pubchem Compound ID397
Pubchem Substance IDNot Available
ChEBI ID16031
Phenol-Explorer IDNot Available
DrugBank IDDB08652
HMDB IDHMDB29739
CRC / DFC (Dictionary of Food Compounds) IDBNC14-M:BND20-Q
EAFUS IDNot Available
Dr. Duke IDINDOLE-3-ACETAMIDE
BIGG IDNot Available
KNApSAcK IDC00000108
HET IDTSR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).