INDOLE

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 Search

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Camphor 5-monooxygenase 1 Target ID: P00183 Gene ID: NA Gene Symbol: camC Target Organism: Pseudomonas putida (Arthrobacter siderocapsulatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16027900	Substrate 661
Tryptophan synthase beta chain 2 Target ID: P0A879 Gene ID: 945768.0 Gene Symbol: trpB Target Organism: Escherichia coli (strain K12) Sources: https://www.ebi.ac.uk/interpro/entry/IPR006654	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Sleep disorder 20 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of sleep disorders
Nasal sinus congestion 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of nasal sinus congestion
Improper digestion 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of improper digestion

PubMed

Title	Date	PubMed
Chestnutamide: a novel alkaloid from flowers of Castanea mollissima Blume.	2001	11407819
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.	2001	11375052
Assignment of the 1511 cm(-1) UV resonance Raman marker band of hemoglobin to tryptophan.	2001	11343285
Relative efficacies of indole antioxidants in reducing autoxidation and iron-induced lipid peroxidation in hamster testes.	2001	11329624
Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction.	2001	11255233
Fluorescence quenching of anthracene by indole derivatives in phospholipid bilayers.	2001 Apr	11386677
Synthesis, pharmacological characterization and QSAR studies on 2-substituted indole melatonin receptor ligands.	2001 Apr	11354661
The role of tryptophan in the antibacterial activity of a 15-residue bovine lactoferricin peptide.	2001 Apr	11354462
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	11345696
Crystal structure of cyclodextrin glucanotransferase from alkalophilic Bacillus sp. 1011 complexed with 1-deoxynojirimycin at 2.0 A resolution.	2001 Apr	11275559
A new synthetic method for preparing indole derivatives from 2-keto glycosides.	2001 Apr 12	11383891
Conformational analysis of indole alkaloids corynantheine and dihydrocorynantheine by dynamic 1H NMR spectroscopy and computational methods: steric effects of ethyl vs vinyl group.	2001 Apr 6	11281758
Signal transduction pathways through TRK-A and TRK-B receptors in human neuroblastoma cells.	2001 Feb	11223544
Distribution of the hallucinogens N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine in rat brain following intraperitoneal injection: application of a new solid-phase extraction LC-APcI-MS-MS-isotope dilution method.	2001 Feb 10	11232854
Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea.	2001 Feb 23	11312946
The jasmonate-inducible AP2/ERF-domain transcription factor ORCA3 activates gene expression via interaction with a jasmonate-responsive promoter element.	2001 Jan	11169181
Molecular and biochemical analysis of a Madagascar periwinkle root-specific minovincinine-19-hydroxy-O-acetyltransferase.	2001 Jan	11154328
High-performance liquid chromatographic and capillary electrophoretic enantioseparation of plant growth regulators and related indole compounds using macrocyclic antibiotics as chiral selectors.	2001 Jan 12	11215905
Structural basis for enantiomer binding and separation of a common beta-blocker: crystal structure of cellobiohydrolase Cel7A with bound (S)-propranolol at 1.9 A resolution.	2001 Jan 5	11114249
Novel bone antiresorptive agents that selectively inhibit the osteoclast V-H+-ATPase.	2001 Jan-Feb	11347950
Biosynthesis of 2-aminobenzaldehyde in flowers of Robinia pseudoacacia and Philadelphus coronarius.	2001 Jun	11393514
Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones.	2001 Jun 1	11375024
3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38.	2001 Jun 26	11412109
Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine.	2001 Jun 27	11414824
Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures.	2001 Mar	11352466
The oxidation of indole derivatives catalyzed by horseradish peroxidase is highly chemiluminescent.	2001 Mar 15	11370838
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	11297447
Biotinylated indoles as probes for indole-binding proteins.	2001 Mar-Apr	11312675
Porphyromonas gulae sp. nov., an anaerobic, gram-negative coccobacillus from the gingival sulcus of various animal hosts.	2001 May	11411686
Revision of the structure of ajmalimine.	2001 May	11374979
Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras.	2001 May	11374976
Core formation in apomyoglobin: probing the upper reaches of the folding energy landscape.	2001 May 1	11318635
Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.	2001 May 18	11348132

Patents

Sample Use Guides

In Vivo Use Guide

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 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:18 GMT 2023`
Record UNII	8724FJW4M5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDOLE

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

Common Name

English

NSC-1964

Code

English

FEMA NO. 2593

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

25000