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1H-Indole-3-carboxaldehyde (FDB000934)

Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2020-09-17 15:39:56 UTC
Primary IDFDB000934
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1H-Indole-3-carboxaldehyde
Description1H-Indole-3-carboxaldehyde, also known as 3-formylindole or 3-indolealdehyde, 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. 1H-Indole-3-carboxaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1H-Indole-3-carboxaldehyde has been detected, but not quantified in, several different foods, such as gram beans, brussel sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make 1H-indole-3-carboxaldehyde a potential biomarker for the consumption of these foods. A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.
CAS Number487-89-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP1.92ALOGPS
logP1.78ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.73 m³·mol⁻¹ChemAxon
Polarizability15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H7NO
IUPAC name1H-indole-3-carbaldehyde
InChI IdentifierInChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N
Isomeric SMILESO=CC1=CNC2=C1C=CC=C2
Average Molecular Weight145.158
Monoisotopic Molecular Weight145.052763851
Classification
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
  • Aryl-aldehyde
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.47%; H 4.86%; N 9.65%; O 11.02%DFC
Melting PointMp 197-199°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.68HANSCH,C ET AL. (1995)
Experimental pKapKa2 12.36 (25°,NH)DFC
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)splash10-0007-2900000000-fcb37c6394c016a4e2d02015-03-01View Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-868873ec5dc494bef752Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-868873ec5dc494bef752Spectrum
Predicted GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014j-0900000000-2f4c23a8137235ce4e95Spectrum
Predicted GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1H-Indole-3-carboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-39d11dbd7bebe565fa942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c9a64e9031a8d467a02b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b7ccb1c640ee7aaf06b42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-d434c2e937c83d1ffd7c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-597c804d77e9a7930c9e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-878ab4a0cfc6d8f0e9d02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9400000000-74dbc81ab5e6866559772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9100000000-22b52274e9bec85c94882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-3900000000-b8cbcf3139ea5a3136662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-94ec8ba0db56440ffc3f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00kf-9400000000-baa602f27188a3041af42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00kf-9100000000-345cf6df9ff740e5d9262021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-014i-2900000000-878ab4a0cfc6d8f0e9d02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00kb-0900000000-597c804d77e9a7930c9e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-0900000000-3d2deb9c036b136fd16a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-1900000000-16d2415d939c5aaff4492021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014l-0900000000-d434c2e937c83d1ffd7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014l-0900000000-c9a64e9031a8d467a02b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00kf-0900000000-ba3a2cf1a036ce47cf692021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-68769392454e8a8bc1da2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0be256e552c87fb9650a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-ae05266446e712d329cb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-89f321c95d799e3073a82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-f63834b99989e7eab9cf2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-2900000000-7f76bc218a02b8adc1d02015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID9838
ChEMBL IDCHEMBL147741
KEGG Compound IDC08493
Pubchem Compound ID10256
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29737
CRC / DFC (Dictionary of Food Compounds) IDBNC50-U:BNC50-U
EAFUS IDNot Available
Dr. Duke IDINDOLE-3-CARBOXYALDEHYDE|INDOLE-3-CARBOXALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00000112
HET IDI3A
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).