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Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection.

Benzeneacetonitrile is found in garden cress. Benzeneacetonitrile is isolated from oil of garden cress (Lepidium sativum) and other plant oils.

2H-isoindole is an isoindole and a polycyclic heteroarene. It is a tautomer of a 1H-isoindole. Benzopyrroles with the nitrogen at the number two carbon, in contrast to INDOLES which have the nitrogen adjacent to the six-membered ring.

1-Amino-4-ethynylbenzene http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/46039

Indolizine is a mancude organic heterobicyclic parent and a member of indolizines. Indolizine is a natural product found in Streptomyces antioxidans with data available.

O-tolunitrile is a light blue clear liquid. (NTP, 1992) o-Tolunitrile is a natural product found in Festuca rubra and Glycyrrhiza glabra with data available.

M-tolunitrile is a clear, yellow liquid. (NTP, 1992)

P-tolunitrile is a beige solid at 62.6 °F. (NTP, 1992) p-Tolunitrile is a natural product found in Thulinella chrysantha with data available.