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 A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.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
Synonyms
SynonymSource
Indole-3-carbaldehydeKEGG
1H-Indole-3-carbaldehydeHMDB
1H-Indole-3-carboxaldehdeHMDB
3-FormylindoleHMDB, ChEBI
3-IndolealdehydeHMDB, ChEBI
3-IndolecarbaldehydeHMDB, ChEBI
3-IndolecarboxaldehydeHMDB, ChEBI
3-IndolemethanalHMDB, MeSH
b-IndolylaldehydeHMDB, Generator
beta-IndolylaldehydeHMDB, ChEBI
indol-3-CarbaldehydHMDB
indol-3-CarbaldehydeHMDB
indol-3-CarboxaldehydeHMDB
Indole-3-aldehydeHMDB, ChEBI
INDOLE-3-carboxyaldehydeHMDB
1H-Indole-3-carboxaldehydeChEBI
I3choChEBI
Indole-3-carboxaldehydeChEBI
β-IndolylaldehydeGenerator
1H-Indol-3-yl carboxaldehydeHMDB
1H-Indole-3-aldehydeHMDB
1H-Indole-3-methanalHMDB
3-Formyl-1H-indoleHMDB
3-IndolylformaldehydeHMDB
I3AHMDB
Indole-3-carboxylaldehydeHMDB
Indole-3-formaldehydeHMDB
β-indolylaldehydebiospider
3-indolemethanalbiospider
B-indolylaldehydebiospider
Beta-indolylaldehydebiospider
Indol-3-carbaldehydbiospider
Indol-3-carbaldehydebiospider
Indol-3-carboxaldehydebiospider
INDOLE-3-CARBOXYALDEHYDEbiospider
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-fcb37c6394c016a4e2d0Spectrum
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-39d11dbd7bebe565fa94Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c9a64e9031a8d467a02bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b7ccb1c640ee7aaf06b4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-d434c2e937c83d1ffd7cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-597c804d77e9a7930c9eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-878ab4a0cfc6d8f0e9d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9400000000-74dbc81ab5e686655977Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9100000000-22b52274e9bec85c9488Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-3900000000-b8cbcf3139ea5a313666Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-94ec8ba0db56440ffc3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-68769392454e8a8bc1daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0be256e552c87fb9650aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-ae05266446e712d329cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-89f321c95d799e3073a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-f63834b99989e7eab9cfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-2900000000-7f76bc218a02b8adc1d0Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
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).