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Chemical Compound Review:

PubChem1692 1H-indole-3-carboxylic acid

Synonyms: SureCN64182, CHEMBL387527, ACMC-1BDYE, AG-B-83533, AG-G-73384, ...

Tan, J. et al., Moran, P.M. et al., Romanelli, M.N. et al., Längle, U.W. et al., Anderton, M.J. et al., et al.

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Disease relevance of MLS-0065969.P001

Formation of indole-3-carboxylic acid by Chromobacterium violaceum [1].
3beta,22alpha-Dihydroxyolean-12-en-29-oic acid (10), indole-3-carboxylic acid (11), 5,7-dihydroxychromone (12), and (-)-catechin (13) demonstrated significant activity against HIV replication in H9 lymphocyte cells [2].
Several of these compounds, particularly indole-3-carboxylic acid, 4-hydroxybenzoic acid and all four aldehydes, increased considerably in concentration upon infection of roots with Pythium sylvaticum, as did at least some of them upon infection of leaves with Pseudomonas syringae pv tomato [3].

High impact information on MLS-0065969.P001

In addition to acid condensation products of I3C, a major oxidative metabolite (indole-3-carboxylic acid) and a minor oxidative metabolite (indole-3-carboxaldehyde) were detected in plasma of mice after oral administration of I3C [4].
4. Mice metabolized 3MI to glucuronic acid conjugates of 3,5- or 6-dihydroxy-3-methyloxindole, 5- or 6-hydroxy-3-methyloxindole, and indole-3-carboxylic acid; and unconjugated indole-3-carboxylic acid [5].
1H-indole-3-carboxylic acid, trans-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester methanesulfonate (MDL 73,147EF), a selective 5-HT3 receptor antagonist, significantly facilitated the LI effect observed after 10 preexposures at 0.1 mg/kg but not at 0.01 mg/kg [6].
Two major non-volatile products of the nitrosation reaction were isolated by preparative HPLC and characterized as indole-3-carboxylic acid and N1-nitroso-3-nitromethylindole [7].
SDZ ICT 322, an indole-3-carboxylic acid scopine ester developed for the treatment of delayed gastric emptying, was administered in feed to four groups of 14 male and 14 female Wistar rats at daily doses of 0, 5, 25 or 125 mg/kg/day for 26 weeks [8].

Biological context of MLS-0065969.P001

Indole is formed by the spontaneous decarboxylation of indole-3-carboxylic acid [9].

Gene context of MLS-0065969.P001

Synthesis and biological activity of a series of aryl tropanyl esters and amides chemically related to 1H-indole-3-carboxylic acid endo 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester. Development of a 5-HT4 agonist endowed with potent antinociceptive activity [10].

References

Formation of indole-3-carboxylic acid by Chromobacterium violaceum. Davis, P.J., Gustafson, M.E., Rosazza, J.P. J. Bacteriol. (1976) [Pubmed]
Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Wu, P.L., Lin, F.W., Wu, T.S., Kuoh, C.S., Lee, K.H., Lee, S.J. Chem. Pharm. Bull. (2004) [Pubmed]
Universally occurring phenylpropanoid and species-specific indolic metabolites in infected and uninfected Arabidopsis thaliana roots and leaves. Tan, J., Bednarek, P., Liu, J., Schneider, B., Svatos, A., Hahlbrock, K. Phytochemistry (2004) [Pubmed]
Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice. Anderton, M.J., Manson, M.M., Verschoyle, R.D., Gescher, A., Lamb, J.H., Farmer, P.B., Steward, W.P., Williams, M.L. Clin. Cancer Res. (2004) [Pubmed]
Identification of goat and mouse urinary metabolites of the pneumotoxin, 3-methylindole. Smith, D.J., Skiles, G.L., Appleton, M.L., Carlson, J.R., Yost, G.S. Xenobiotica (1993) [Pubmed]
MDL 73,147EF, a 5-HT3 antagonist, facilitates latent inhibition in the rat. Moran, P.M., Moser, P.C. Pharmacol. Biochem. Behav. (1992) [Pubmed]
Isolation and characterization of products from the nitrosation of the alkaloid gramine. Ahmad, M.U., Libbey, L.M., Barbour, J.F., Scanlan, R.A. Food Chem. Toxicol. (1985) [Pubmed]
Cataractogenic effects in rats following chronic administration of SDZ ICT 322, a selective 5-HT3 antagonist. Längle, U.W., Wolf, A., Kammüller, M.E. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1993) [Pubmed]
The metabolism of tryptophan and 7-chlorotryptophan in Pseudomonas pyrrocinia and Pseudomonas aureofaciens. Lübbe, C., van Pée, K.H., Salcher, O., Lingens, F. Hoppe-Seyler's Z. Physiol. Chem. (1983) [Pubmed]
Synthesis and biological activity of a series of aryl tropanyl esters and amides chemically related to 1H-indole-3-carboxylic acid endo 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester. Development of a 5-HT4 agonist endowed with potent antinociceptive activity. Romanelli, M.N., Ghelardini, C., Dei, S., Matucci, R., Mori, F., Scapecchi, S., Teodori, E., Bartolini, A., Galli, A., Giotti, A. Arzneimittel-Forschung. (1993) [Pubmed]

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