Showing metabocard for Indoleacetaldehyde (BMDB0001190)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:19 UTC
Update Date2020-05-21 16:28:51 UTC
BMDB IDBMDB0001190
Secondary Accession Numbers
  • BMDB01190
Metabolite Identification
Common NameIndoleacetaldehyde
DescriptionIndoleacetaldehyde 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. Indoleacetaldehyde is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Indoleacetaldehyde participates in a number of enzymatic reactions, within cattle. In particular, Indoleacetaldehyde can be biosynthesized from tryptamine through the action of the enzyme kynurenine 3-monooxygenase. In addition, Indoleacetaldehyde can be converted into indoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In cattle, indoleacetaldehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1H-Indole-3-acetaldehydeChEBI
2-(indol-3-yl)AcetaldehydeChEBI
Indole-3-acetaldehydeChEBI
1H-indol-3-YlacetaldehydeHMDB
2-(3-Indolyl)acetaldehydeHMDB
indol-3-YlacetaldehydeHMDB
TryptaldehydeHMDB
Chemical FormulaC10H9NO
Average Molecular Weight159.1846
Monoisotopic Molecular Weight159.068413915
IUPAC Name2-(1H-indol-3-yl)acetaldehyde
Traditional Nameindole-3-acetaldehyde
CAS Registry Number2591-98-2
SMILES
O=CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3790000000-d0624211b87a8c0c6eb0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fb9-1890000000-f47966a3402f39ffb15aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufr-2890000000-4661feb288e5418df124View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1669000000-87b7c126c24be968871eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-0910000000-f73cd81db2b9712b4661View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1490000000-614e405de09537fc4b35View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-c2d7214f3eaf0a20e864View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-75194e386ef16f3f47b2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3790000000-d0624211b87a8c0c6eb0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fb9-1890000000-f47966a3402f39ffb15aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-2890000000-4661feb288e5418df124View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1669000000-87b7c126c24be968871eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0910000000-f73cd81db2b9712b4661View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1490000000-614e405de09537fc4b35View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-0900000000-4528170aed93d1f2f6cfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a7i-0900000000-3a12e240a01798e6d515View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-0d6b7064551a83893c6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-0900000000-868e767ca141d74ec888View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0059-0900000000-dea5f8a3cd655d34e727View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-0900000000-03eb4dd9323023a06970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ec1cff588ddd81294ce1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-a292bcb2abf1d2004296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yl-0900000000-c9491489626575ac821cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-3900000000-c4a5850dd4b1a7da14e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8354b2e6155a5677c353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-2bd561638cdcf5535ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-3900000000-bb8a2da37c41a8f5040eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0api-0900000000-ab705375598dd738ce6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-924d3410f1e3855c2336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-74f0d61a0a5ca7d19925View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0900000000-f09223778d8ebf23f2f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-474bb30e410332db437aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-3900000000-8e24fed06b1ae0ed20afView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001190
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013950
KNApSAcK IDC00000109
Chemspider ID778
KEGG Compound IDC00637
BioCyc IDINDOLE_ACETALDEHYDE
BiGG ID35561
Wikipedia LinkNot Available
METLIN ID6068
PubChem Compound800
PDB IDNot Available
ChEBI ID18086
References
Synthesis ReferenceGray, Reed A. Preparation and properties of 3-indoleacetaldehyde. Archives of Biochemistry and Biophysics (1959), 81 480-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Kynurenine 3-monooxygenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
KMO
Uniprot ID:
E1BN59
Molecular weight:
51032.0
Reactions
Tryptamine + NADPH + Oxygen → Indoleacetaldehyde + NADP + Waterdetails