Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H9NO2 |
Molecular Weight | 175.1843 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc2c(c1)c(CC(=O)O)c[nH]2
InChI
InChIKey=SEOVTRFCIGRIMH-UHFFFAOYSA-N
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
Molecular Formula | C10H9NO2 |
Molecular Weight | 175.1843 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Indoleacetic acid is the most abundant and basic plant hormone of auxin class. In plants, it plays a key role in both roots and shoots development. In mammals, indoleacetic acid is often produced by the action of gut bacteria. Elevated levels of indoleacetic acid have been found in the urine of patients with phenylketonuria. Indoleacetic acid was evaluated as a photosensitizer for acne treatment.
Originator
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/21412803 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Serotonin metabolism is pellagra. | 1975 Oct |
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Selection and evaluation of Azospirillum brasilense strains growing at a sub-optimum temperature in rhizocoenosis with wheat. | 2001 |
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[Metabolism and transport of auxin in plants]. | 2001 |
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Suppression of maize root diseases caused by Macrophomina phaseolina, Fusarium moniliforme and Fusarium graminearum by plant growth promoting rhizobacteria. | 2001 |
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Gravitropism in cut flower stalks of snapdragon. | 2001 |
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Involvement of gacS and rpoS in enhancement of the plant growth-promoting capabilities of Enterobacter cloacae CAL2 and UW4. | 2001 Aug |
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Characterization of two tomato aquaporins and expression during the incompatible interaction of tomato with the plant parasite Cuscuta reflexa. | 2001 Aug |
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Oxidative stress, growth factor production and budding in potato tubers during cold storage. | 2001 Dec |
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Quantitative analysis of indole-3-acetic acid metabolites in Arabidopsis. | 2001 Dec |
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Bioactivity of 25-hydroxy-, 26-hydroxy, 25,26-dihydroxy- and 25,26-epoxybrassinolide. | 2001 Dec |
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[Cloning and identification of an Agrobacterium radiobacter 5D-1 chromosome fragment involved in control of nitrogen metabolism, biosynthesis of indolylacetic acid and replication of ColE1 plasmids]. | 2001 Jul |
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[Aerobic methylobacteria are capable of synthesizing auxins]. | 2001 Jul-Aug |
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Auxin promotes gibberellin biosynthesis in decapitated tobacco plants. | 2001 Nov |
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Sites and homeostatic control of auxin biosynthesis in Arabidopsis during vegetative growth. | 2001 Nov |
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Maize VP1 complements Arabidopsis abi3 and confers a novel ABA/auxin interaction in roots. | 2001 Nov |
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Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine. | 2001 Nov |
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The Arabidopsis pxa1 mutant is defective in an ATP-binding cassette transporter-like protein required for peroxisomal fatty acid beta-oxidation. | 2001 Nov |
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Attenuation of phosphate starvation responses by phosphite in Arabidopsis. | 2001 Nov |
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A basic peroxidase from wheat kernel with antifungal activity. | 2001 Nov |
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Auxin regulates SCF(TIR1)-dependent degradation of AUX/IAA proteins. | 2001 Nov 15 |
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Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase. | 2001 Nov 2 |
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Hormonal regulation of tissue-specific ectopic expression of an Arabidopsis endoplasmic reticulum-type omega-3 fatty acid desaturase (FAD3) gene. | 2001 Oct |
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IAA and N(6)-benzyladenine inhibit ethylene-regulated expression of ACC oxidase and ACC synthase genes in mungbean hypocotyls. | 2001 Oct |
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Auxin signalling: the beginning, the middle and the end. | 2001 Oct |
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Auxin and the power of the proteasome in plants. | 2001 Oct |
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Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection. | 2001 Oct |
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Localization of the auxin permease AUX1 suggests two functionally distinct hormone transport pathways operate in the Arabidopsis root apex. | 2001 Oct 15 |
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Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide. | 2001 Oct 19 |
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Alterations in plant growth and in root hormone levels of lodgepole pines inoculated with rhizobacteria. | 2001 Sep |
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Arabidopsis mutants with increased organ regeneration in tissue culture are more competent to respond to hormonal signals. | 2001 Sep |
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The auxin signal for protoplast swelling is perceived by extracellular ABP1. | 2001 Sep |
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Ab initio Hartree-Fock investigation of 1-H-pyrrolo[3,2-b]pyridine-3-yl acetic acid. | 2001 Sep 1 |
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Optimisation of transgene action at the post-transcriptional level: high quality parthenocarpic fruits in industrial tomatoes. | 2002 |
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Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery. | 2002 Apr |
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Arabidopsis SHY2/IAA3 inhibits auxin-regulated gene expression. | 2002 Feb |
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An emerging model of auxin transport regulation. | 2002 Feb |
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Organogenesis and terpenoid synthesis in Mentha arvensis. | 2002 Feb |
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Shoot-derived auxin is essential for early lateral root emergence in Arabidopsis seedlings. | 2002 Feb |
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Gravity-stimulated changes in auxin and invertase gene expression in maize pulvinal cells. | 2002 Feb |
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FQR1, a novel primary auxin-response gene, encodes a flavin mononucleotide-binding quinone reductase. | 2002 Feb |
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Analysis of plant hormones in tobacco flowers by micellar electrokinetic capillary chromatography coupled with on-line large volume sample stacking. | 2002 Feb 1 |
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Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. | 2002 Jan |
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Arabidopsis cytochrome P450 cyp83B1 mutations activate the tryptophan biosynthetic pathway. | 2002 Jan |
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5-Fluoroindole-3-acetic acid: a prodrug activated by a peroxidase with potential for use in targeted cancer therapy. | 2002 Jan 15 |
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A novel bifunctional molybdo-enzyme catalyzing both decarboxylation of indolepyruvate and oxidation of indoleacetaldehyde from a thermoacidophilic archaeon, Sulfolobus sp. strain 7. | 2002 Jan 16 |
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Delayed abscission and shorter Internodes correlate with a reduction in the ethylene receptor LeETR1 transcript in transgenic tomato. | 2002 Mar |
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Oxic and anoxic enhancement of radiation-mediated toxicity by horseradish peroxidase/indole-3-acetic acid gene therapy. | 2002 Mar |
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Synthesis and bioactivity of C-2 and C-3 methyl ether derivatives of brassinolide. | 2002 Mar |
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Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. | 2002 Mar |
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Crystal structures of a new class of allosteric effectors complexed to tryptophan synthase. | 2002 Mar 22 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21412803
As a photosensitizer for the treatment of acne, 0.015% formulation of indoleacetic acid was applied topically.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13610897
To determine the level of indoleacetic acid in the urine, 4 ml of urine in a 40-ml glass-stoppered centrifuge tube wase acidified by the addition of 0.36 ml. of 12 N HCI. 10 ml. of CHCl3 were added and the tube was shaken for 5 minutes. After centrifugation 9 ml. of the CHCl3 were transferred to another 40 ml glass-stoppered centrifuge tube containing 0.6 ml. of 0.5 M phosphate buffer, pH 7.0. The tube was shaken for 5 minutes and the CHCl3 layer was aspirated and discarded. An aliquot of the buffer was then assayed calorimetrically by the use of a modification of the xanthydrol reaction of Dickman and Crockett (4) as follows: 0.4 ml. of the pH 7.0 buffer extract was transferred to a test tube containing 0.4 ml. of 12 N HCl; 1 ml. of the xanthydrol reagent was added, followed 5 minutes later by 0.5 ml. of the bisulfite reagent. The solution was mixed and the pink color measured within 5 to 10 minutes at 520 nm in a spectrophotometer.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 03:32:30 UTC 2021
by
admin
on
Sat Jun 26 03:32:30 UTC 2021
|
Record UNII |
6U1S09C61L
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Record Status |
Validated (UNII)
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Record Version |
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-
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EPA PESTICIDE CODE |
128915
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802
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Indoleacetic acid
Created by
admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
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