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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:58 UTC
HMDB IDHMDB01190
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndoleacetaldehyde
DescriptionIndoleacetaldehyde is a substrate for Retina-specific copper amine oxidase, Aldehyde dehydrogenase X (mitochondrial), Amine oxidase B, Amiloride-sensitive amine oxidase, Aldehyde dehydrogenase (mitochondrial), Fatty aldehyde dehydrogenase, 4-trimethylaminobutyraldehyde dehydrogenase, Aldehyde dehydrogenase (dimeric NADP-preferring), Aldehyde dehydrogenase family 7 member A1, Amine oxidase A, Aldehyde dehydrogenase 1A3 and Membrane copper amine oxidase.
Structure
Thumb
Synonyms
ValueSource
1H-Indole-3-acetaldehydeChEBI
2-(indol-3-yl)AcetaldehydeChEBI
Indole-3-acetaldehydeChEBI
IndoleacetaldehydeChEBI
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=CC=CC=C12
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 KeyInChIKey=WHOOUMGHGSPMGR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These 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
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Alpha-hydrogen aldehyde
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and 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
Water Solubility1.01 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.53 m3·mol-1ChemAxon
Polarizability16.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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-MSsplash10-0udi-1490000000-614e405de09537fc4b35View 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified7.24 +/- 1.16 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013950
KNApSAcK IDC00000109
Chemspider ID778
KEGG Compound IDC00637
BioCyc IDINDOLE_ACETALDEHYDE
BiGG ID35561
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01190
Metagene LinkHMDB01190
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 References
  1. Tottmar O, Hellstrom E: Aldehyde dehydrogenase in blood: a sensitive assay and inhibition by disulfiram. Pharmacol Biochem Behav. 1983;18 Suppl 1:103-7. [6634824 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails