Showing Compound Card for Indole-3-carboxaldehyde (CDB005045)

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Record Information
Version1.0
Created at2020-04-17 19:03:46 UTC
Updated at2020-11-18 16:39:14 UTC
CannabisDB IDCDB005045
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIndole-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 A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group. Indole-3-carboxaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1H-Indole-3-carboxaldehydeChEBI
3-FormylindoleChEBI
3-IndolealdehydeChEBI
3-IndolecarbaldehydeChEBI
3-IndolecarboxaldehydeChEBI
beta-IndolylaldehydeChEBI
I3choChEBI
Indole-3-aldehydeChEBI
Indole-3-carbaldehydeKegg
b-IndolylaldehydeGenerator
Β-indolylaldehydeGenerator
3-IndolemethanalMeSH
1H-Indole-3-carbaldehydeHMDB
1H-Indole-3-carboxaldehdeHMDB
indol-3-CarbaldehydHMDB
indol-3-CarbaldehydeHMDB
indol-3-CarboxaldehydeHMDB
INDOLE-3-carboxyaldehydeHMDB
Indole-3-carboxaldehydeChEBI
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
Chemical FormulaC9H7NO
Average Molecular Weight145.16
Monoisotopic Molecular Weight145.0528
IUPAC Name1H-indole-3-carbaldehyde
Traditional Nameindole-3-carboxaldehyde
CAS Registry Number487-89-8
SMILES
O=CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.68Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0007-2900000000-fcb37c6394c016a4e2d02015-03-01View Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-868873ec5dc494bef752Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MSIndole-3-carboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-868873ec5dc494bef752Spectrum
Predicted GC-MSIndole-3-carboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014j-0900000000-2f4c23a8137235ce4e95Spectrum
Predicted GC-MSIndole-3-carboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIndole-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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029737
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000934
KNApSAcK IDC00000112
Chemspider ID9838
KEGG Compound IDC08493
BioCyc IDINDOLE-3-CARBOXALDEHYDE
BiGG IDNot Available
Wikipedia LinkIndole-3-carboxaldehyde
METLIN IDNot Available
PubChem Compound10256
PDB IDI3A
ChEBI ID28238
References
General ReferencesNot Available