Record Information
Version1.0
Creation date2010-04-08 22:11:00 UTC
Update date2020-09-17 15:38:50 UTC
Primary IDFDB013950
Secondary Accession Numbers
  • FDB030918
Chemical Information
FooDB Name1H-Indole-3-acetaldehyde
DescriptionIndoleacetaldehyde, also known as tryptaldehyde, 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. An indoleacetaldehyde that is acetaldehyde in which one of the methyl hydrogens are replaced by a indol-3-yl group. Indoleacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, indoleacetaldehyde participates in a number of enzymatic reactions. In particular, indoleacetaldehyde can be biosynthesized from tryptamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In addition, indoleacetaldehyde can be converted into indoleacetic acid through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, indoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, Indoleacetaldehyde has been detected, but not quantified in, several different foods, such as ohelo berries, mamey sapotes, turnips, chives, and pummelo. This could make indoleacetaldehyde a potential biomarker for the consumption of these foods.
CAS Number2591-98-2
Structure
Thumb
Synonyms
SynonymSource
1H-Indole-3-acetaldehydeChEBI
2-(indol-3-yl)AcetaldehydeChEBI
Indole-3-acetaldehydeChEBI
1H-indol-3-YlacetaldehydeHMDB
2-(3-Indolyl)acetaldehydeHMDB
indol-3-YlacetaldehydeHMDB
TryptaldehydeHMDB
3-(Formylmethyl)indoledb_source
b-Indolylacetaldehydedb_source
IndoleacetaldehydeChEBI
Skototenindb_source
Predicted Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP2.32ALOGPS
logP1.55ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.53 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H9NO
IUPAC name2-(1H-indol-3-yl)acetaldehyde
InChI IdentifierInChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
InChI KeyWHOOUMGHGSPMGR-UHFFFAOYSA-N
Isomeric SMILESO=CCC1=CNC2=CC=CC=C12
Average Molecular Weight159.1846
Monoisotopic Molecular Weight159.068413915
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
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydrogen aldehyde
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 stateSolid
Physical DescriptionNot Available
Mass CompositionC 75.45%; H 5.70%; N 8.80%; O 10.05%DFC
Melting PointNot Available
Boiling PointBp0.00005 120°DFC
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
GC-MS1H-Indole-3-acetaldehyde, 1 TMS, GC-MS Spectrumsplash10-0udi-3790000000-d0624211b87a8c0c6eb0Spectrum
GC-MS1H-Indole-3-acetaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0fb9-1890000000-f47966a3402f39ffb15aSpectrum
GC-MS1H-Indole-3-acetaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0ufr-2890000000-4661feb288e5418df124Spectrum
GC-MS1H-Indole-3-acetaldehyde, 2 TMS, GC-MS Spectrumsplash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2Spectrum
GC-MS1H-Indole-3-acetaldehyde, 2 TMS, GC-MS Spectrumsplash10-0udi-1669000000-87b7c126c24be968871eSpectrum
GC-MS1H-Indole-3-acetaldehyde, 3 TMS, GC-MS Spectrumsplash10-0006-0910000000-f73cd81db2b9712b4661Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udi-1490000000-614e405de09537fc4b35Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-c2d7214f3eaf0a20e864Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-75194e386ef16f3f47b2Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udi-3790000000-d0624211b87a8c0c6eb0Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0fb9-1890000000-f47966a3402f39ffb15aSpectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0ufr-2890000000-4661feb288e5418df124Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udi-1669000000-87b7c126c24be968871eSpectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-f73cd81db2b9712b4661Spectrum
GC-MS1H-Indole-3-acetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udi-1490000000-614e405de09537fc4b35Spectrum
Predicted GC-MS1H-Indole-3-acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-0900000000-4528170aed93d1f2f6cfSpectrum
Predicted GC-MS1H-Indole-3-acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1H-Indole-3-acetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a7i-0900000000-3a12e240a01798e6d515Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-0d6b7064551a83893c6eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-0900000000-868e767ca141d74ec888Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0059-0900000000-dea5f8a3cd655d34e727Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-0900000000-03eb4dd9323023a06970Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ec1cff588ddd81294ce1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-a292bcb2abf1d2004296Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yl-0900000000-c9491489626575ac821cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-3900000000-c4a5850dd4b1a7da14e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8354b2e6155a5677c353Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-2bd561638cdcf5535ba5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-3900000000-bb8a2da37c41a8f5040eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0api-0900000000-ab705375598dd738ce6dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-924d3410f1e3855c2336Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-74f0d61a0a5ca7d19925Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0900000000-f09223778d8ebf23f2f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-474bb30e410332db437aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-3900000000-8e24fed06b1ae0ed20afSpectrum
NMRNot Available
ChemSpider ID778
ChEMBL IDNot Available
KEGG Compound IDC00637
Pubchem Compound ID800
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01190
CRC / DFC (Dictionary of Food Compounds) IDJKZ09-O:JKZ09-O
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35561
KNApSAcK IDC00000109
HET IDNot Available
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
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
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.