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Details

Stereochemistry ACHIRAL
Molecular Formula C8H7N
Molecular Weight 117.1479
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOLE

SMILES

N1C=CC2=C1C=CC=C2

InChI

InChIKey=SIKJAQJRHWYJAI-UHFFFAOYSA-N
InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

HIDE SMILES / InChI

Molecular Formula C8H7N
Molecular Weight 117.1479
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Sources: DOI: 10.5772/62079
Curator's Comment: description was created based on several sources, including: doi: 10.1007/7081_2010_48 http://www.ijpsr.info/docs/IJPSR16-07-02-101.pdf

Indoles and their derivatives are well-known as an important class of heterocyclic compounds, their core being a near-ubiquitous component of biologically active natural products, widespread in different species of plants, animals, and marine organisms. The indole is also well-known as one of the most important scaffolds for drug discovery, capable of serving as ligand for a diverse array of receptors. Indoles is used in textile dyes, perfumes, in agriculture and veterinary medicine. Relatively new areas are dietary supplements and nutraceuticals.

Originator

Sources: DOI: 10.1002/cber.186900201268 | DOI: 10.1021/cr60095a004

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P00183
Gene ID: NA
Gene Symbol: camC
Target Organism: Pseudomonas putida (Arthrobacter siderocapsulatus)
Target ID: P0A879
Gene ID: 945768.0
Gene Symbol: trpB
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
INDOLE

Approved Use

It is used for temporary relief of symptoms of sleep disorders
Palliative
INDOLE

Approved Use

It is used for temporary relief of symptoms of nasal sinus congestion
Palliative
INDOLE

Approved Use

It is used for temporary relief of symptoms of improper digestion
PubMed

PubMed

TitleDatePubMed
Chestnutamide: a novel alkaloid from flowers of Castanea mollissima Blume.
2001
Assignment of the 1511 cm(-1) UV resonance Raman marker band of hemoglobin to tryptophan.
2001
Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.
2001 Apr
DNA binding properties of the marine sponge pigment fascaplysin.
2001 Apr
The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.
2001 Apr
Crystal structure of cyclodextrin glucanotransferase from alkalophilic Bacillus sp. 1011 complexed with 1-deoxynojirimycin at 2.0 A resolution.
2001 Apr
A new synthetic method for preparing indole derivatives from 2-keto glycosides.
2001 Apr 12
Acylation of indole under Friedel-Crafts conditions-an improved method to obtain 3-acylindoles regioselectively.
2001 Apr 5
[Diagnosis of swine dysentery and spirochaetal diarrhea. III. Results of cultural and biochemical differentiation of intestinal Brachyspira species by routine culture from 1997 to 1999].
2001 Feb
Trapping of the putative cationic intermediate in the Morin rearrangement with carbon nucleophiles.
2001 Feb 9
Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.
2001 Jan 12
Synthesis of novel analogues of marine indole alkaloids: mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents.
2001 Jul
Modification of voltage-dependent gating of potassium channels by free form of tryptophan side chain.
2001 Jul
Proteins with beta-(thienopyrrolyl)alanines as alternative chromophores and pharmaceutically active amino acids.
2001 Jul
Identification of glucosinolates on the leaf surface of plants from the Cruciferae and other closely related species.
2001 Jul
Dynamic features of the subunit interface of Cu,Zn superoxide dismutase as probed by tryptophan phosphorescence.
2001 Jul 1
Substituted indole-5-carboxamides and -acetamides as potent nonpeptide GnRH receptor antagonists.
2001 Jul 9
Effects of indole on breathing in rats.
2001 Jun
Methyl chanofruticosinates from leaves of Kopsia flavida Blume.
2001 Jun
Biosynthesis of 2-aminobenzaldehyde in flowers of Robinia pseudoacacia and Philadelphus coronarius.
2001 Jun
Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones.
2001 Jun 1
A new and general synthetic pathway to strychnos indole alkaloids: total syntheses of (-)-dehydrotubifoline and (-)-tubifoline by palladium-catalyzed asymmetric allylic substitution.
2001 Jun 14
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.
2001 Jun 15
Incorporation of beta-selenolo[3,2-b]pyrrolyl-alanine into proteins for phase determination in protein X-ray crystallography.
2001 Jun 15
Transformation of a kappa-opioid receptor antagonist to a kappa-agonist by transfer of a guanidinium group from the 5'- to 6'-position of naltrindole.
2001 Jun 21
3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38.
2001 Jun 26
Beta D305A mutant of tryptophan synthase shows strongly perturbed allosteric regulation and substrate specificity.
2001 Jun 26
Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine.
2001 Jun 27
Synthesis of ent-alantrypinone.
2001 Jun 27
Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction.
2001 Jun 29
Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures.
2001 Mar
Evidence for a direct effect of melatonin on mitochondrial genome expression of Siberian hamster brown adipocytes.
2001 Mar
The oxidation of indole derivatives catalyzed by horseradish peroxidase is highly chemiluminescent.
2001 Mar 15
New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.
2001 Mar 15
Discovery and optimization of a novel series of thrombin receptor (par-1) antagonists: potent, selective peptide mimetics based on indole and indazole templates.
2001 Mar 29
Calcium/calmodulin-dependent protein kinase inhibition potentiates thapsigargin-mediated cell death in SH-SY5Y human neuroblastoma cells.
2001 Mar 30
Insights into the genetic diversity of initial dioxygenases from PAH-degrading bacteria.
2001 May
Porphyromonas gulae sp. nov., an anaerobic, gram-negative coccobacillus from the gingival sulcus of various animal hosts.
2001 May
Revision of the structure of ajmalimine.
2001 May
Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras.
2001 May
Lignin peroxidase structure and function.
2001 May
The role of distal tryptophan in the bifunctional activity of catalase-peroxidases.
2001 May
ORCAnization of jasmonate-responsive gene expression in alkaloid metabolism.
2001 May
3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT(2A) receptor antagonists.
2001 May 10
Thiazole analogues of the NSAID indomethacin as selective COX-2 inhibitors.
2001 May 21
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.
2001 May 24
Expression of the Caldariomyces fumago chloroperoxidase in Aspergillus niger and characterization of the recombinant enzyme.
2001 May 25
Efficient syntheses of novel C2'-alkylated (+/-)-K252a analogues.
2001 May 31
2-Aryl indole NK1 receptor antagonists: optimisation of indole substitution.
2001 May 7
New selectivity in peptide hydrolysis by metal complexes. Platinum(II) complexes promote cleavage of peptides next to the tryptophan residue.
2001 May 7
Patents

Sample Use Guides

1-10 drops under the tongue, 3 times a day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:18 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:18 UTC 2023
Record UNII
8724FJW4M5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDOLE
FCC   FHFI   HSDB   MI  
Systematic Name English
INDOLE [FCC]
Common Name English
INDOLE [HSDB]
Common Name English
INDOLE [MI]
Common Name English
INDOLE [USP-RS]
Common Name English
INDOLUM [HPUS]
Common Name English
INDOLE [FHFI]
Common Name English
2,3-BENZOPYRROLE
Common Name English
INDOLUM
HPUS  
Common Name English
NSC-1964
Code English
FEMA NO. 2593
Code English
Classification Tree Code System Code
EPA PESTICIDE CODE 25000
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
JECFA EVALUATION INDOLE
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
LOINC 2477-8
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Code System Code Type Description
EVMPD
SUB90866
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PRIMARY
RXCUI
1311224
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PRIMARY RxNorm
CHEBI
35581
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PRIMARY
DAILYMED
8724FJW4M5
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PRIMARY
HSDB
599
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PRIMARY
EPA CompTox
DTXSID0020737
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PRIMARY
JECFA MONOGRAPH
1185
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PRIMARY
NSC
1964
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PRIMARY
MESH
C030374
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PRIMARY
CHEBI
16881
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PRIMARY
DRUG BANK
DB04532
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PRIMARY
CAS
120-72-9
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PRIMARY
PUBCHEM
798
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PRIMARY
ECHA (EC/EINECS)
204-420-7
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PRIMARY
WIKIPEDIA
INDOLE
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
PRIMARY
RS_ITEM_NUM
1340086
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PRIMARY
FDA UNII
8724FJW4M5
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
PRIMARY
SMS_ID
100000141120
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
PRIMARY
NCI_THESAURUS
C68534
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
PRIMARY
MERCK INDEX
m6273
Created by admin on Fri Dec 15 15:15:19 UTC 2023 , Edited by admin on Fri Dec 15 15:15:19 UTC 2023
PRIMARY Merck Index
Related Record Type Details
DERIVATIVE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
Formed from tryptophanase from gut bacteria.
Related Record Type Details
ACTIVE MOIETY