Identification

Generic Name
Indoleacetamide
DrugBank Accession Number
DB08652
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 174.1992
Monoisotopic: 174.079312952
Chemical Formula
C10H10N2O
Synonyms
  • 1H-indole-3-acetamide
  • 3-indoleacetamide
  • Indole-3-acetamide

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAralkylamine dehydrogenase light chainNot AvailableAlcaligenes faecalis
UAralkylamine dehydrogenase heavy chainNot AvailableAlcaligenes faecalis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indoles, acetamides (CHEBI:16031) / a small molecule (CPD-237)
Affected organisms
Not Available

Chemical Identifiers

UNII
O9SEW65XW3
CAS number
879-37-8
InChI Key
ZOAMBXDOGPRZLP-UHFFFAOYSA-N
InChI
InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
IUPAC Name
2-(1H-indol-3-yl)acetamide
SMILES
NC(=O)CC1=CNC2=CC=CC=C12

References

General References
Not Available
Human Metabolome Database
HMDB0029739
KEGG Compound
C02693
PubChem Compound
397
PubChem Substance
99445123
ChemSpider
386
ChEBI
16031
ZINC
ZINC000000409269
PDBe Ligand
TSR
PDB Entries
2oiz / 2ojy / 4iv9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.67 mg/mLALOGPS
logP1.17ALOGPS
logP0.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.94ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.88 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.27 m3·mol-1ChemAxon
Polarizability18.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.9964
Caco-2 permeable-0.5723
P-glycoprotein substrateNon-substrate0.6754
P-glycoprotein inhibitor INon-inhibitor0.9669
P-glycoprotein inhibitor IINon-inhibitor0.9571
Renal organic cation transporterNon-inhibitor0.7927
CYP450 2C9 substrateNon-substrate0.8779
CYP450 2D6 substrateNon-substrate0.809
CYP450 3A4 substrateNon-substrate0.6662
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.8939
CYP450 2D6 inhibitorNon-inhibitor0.6643
CYP450 2C19 inhibitorNon-inhibitor0.8226
CYP450 3A4 inhibitorNon-inhibitor0.6399
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5295
Ames testNon AMES toxic0.8933
CarcinogenicityNon-carcinogens0.9077
BiodegradationNot ready biodegradable0.9294
Rat acute toxicity1.7630 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.992
hERG inhibition (predictor II)Non-inhibitor0.9019
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-000i-1940000000-2e0b818a401b68b37cb0
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0udi-1690000000-bd0b44e69af5595426d5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-1940000000-2e0b818a401b68b37cb0
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-1690000000-bd0b44e69af5595426d5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0690000000-7d97254bac7f634f8ef6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0790000000-3baf5bdb295590ef5e30
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0490000000-68d3c7497fdc144df3ff
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0962600000-44dab9af3d483d324860
Mass Spectrum (Electron Ionization)MSsplash10-001i-4900000000-6404e04bc67c64bf01fe
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0900000000-1f155ed0ed5f83f86725
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0900000000-07eabe3745639209f133
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1900000000-b726329bdc2f6e86c331
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-a3d953ff50b9cf857473
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ec-2900000000-945fb87e55e153b51160
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-8838f76ce5faa9a04337
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-8e500497980b176c3b93
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0089-0900000000-7ed0e1427315880135e9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-fc7d0772d90e4729aef2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0059-3900000000-f1a9ae54e7b833bbf726
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9500000000-1c040087111497793e63
MS/MS Spectrum - , negativeLC-MS/MSsplash10-00e9-0900000000-9f05f0a7e9fe3835ecf3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-67ccc2768cce859f2499
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Alcaligenes faecalis
Pharmacological action
Unknown
General Function
Aralkylamine dehydrogenase (azurin) activity
Specific Function
Oxidizes primary aromatic amines and, more slowly, some long-chain aliphatic amines, but not methylamine or ethylamine. Uses azurin as an electron acceptor to transfer electrons from the reduced tr...
Gene Name
aauA
Uniprot ID
P84887
Uniprot Name
Aralkylamine dehydrogenase light chain
Molecular Weight
19651.915 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Alcaligenes faecalis
Pharmacological action
Unknown
General Function
Aralkylamine dehydrogenase (azurin) activity
Specific Function
Oxidizes primary aromatic amines and, more slowly, some long-chain aliphatic amines, but not methylamine or ethylamine. Uses azurin as an electron acceptor to transfer electrons from the reduced tr...
Gene Name
aauB
Uniprot ID
P84888
Uniprot Name
Aralkylamine dehydrogenase heavy chain
Molecular Weight
42924.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52