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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
Structure of INDOLEACETIC ACID

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)

HIDE SMILES / InChI

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Serotonin metabolism is pellagra.
1975 Oct
Selection and evaluation of Azospirillum brasilense strains growing at a sub-optimum temperature in rhizocoenosis with wheat.
2001
[Metabolism and transport of auxin in plants].
2001
Suppression of maize root diseases caused by Macrophomina phaseolina, Fusarium moniliforme and Fusarium graminearum by plant growth promoting rhizobacteria.
2001
Gravitropism in cut flower stalks of snapdragon.
2001
Involvement of gacS and rpoS in enhancement of the plant growth-promoting capabilities of Enterobacter cloacae CAL2 and UW4.
2001 Aug
Characterization of two tomato aquaporins and expression during the incompatible interaction of tomato with the plant parasite Cuscuta reflexa.
2001 Aug
Oxidative stress, growth factor production and budding in potato tubers during cold storage.
2001 Dec
Quantitative analysis of indole-3-acetic acid metabolites in Arabidopsis.
2001 Dec
Bioactivity of 25-hydroxy-, 26-hydroxy, 25,26-dihydroxy- and 25,26-epoxybrassinolide.
2001 Dec
[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
[Aerobic methylobacteria are capable of synthesizing auxins].
2001 Jul-Aug
Auxin promotes gibberellin biosynthesis in decapitated tobacco plants.
2001 Nov
Sites and homeostatic control of auxin biosynthesis in Arabidopsis during vegetative growth.
2001 Nov
Maize VP1 complements Arabidopsis abi3 and confers a novel ABA/auxin interaction in roots.
2001 Nov
Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine.
2001 Nov
The Arabidopsis pxa1 mutant is defective in an ATP-binding cassette transporter-like protein required for peroxisomal fatty acid beta-oxidation.
2001 Nov
Attenuation of phosphate starvation responses by phosphite in Arabidopsis.
2001 Nov
A basic peroxidase from wheat kernel with antifungal activity.
2001 Nov
Auxin regulates SCF(TIR1)-dependent degradation of AUX/IAA proteins.
2001 Nov 15
Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase.
2001 Nov 2
Hormonal regulation of tissue-specific ectopic expression of an Arabidopsis endoplasmic reticulum-type omega-3 fatty acid desaturase (FAD3) gene.
2001 Oct
IAA and N(6)-benzyladenine inhibit ethylene-regulated expression of ACC oxidase and ACC synthase genes in mungbean hypocotyls.
2001 Oct
Auxin signalling: the beginning, the middle and the end.
2001 Oct
Auxin and the power of the proteasome in plants.
2001 Oct
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
Localization of the auxin permease AUX1 suggests two functionally distinct hormone transport pathways operate in the Arabidopsis root apex.
2001 Oct 15
Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide.
2001 Oct 19
Alterations in plant growth and in root hormone levels of lodgepole pines inoculated with rhizobacteria.
2001 Sep
Arabidopsis mutants with increased organ regeneration in tissue culture are more competent to respond to hormonal signals.
2001 Sep
The auxin signal for protoplast swelling is perceived by extracellular ABP1.
2001 Sep
Ab initio Hartree-Fock investigation of 1-H-pyrrolo[3,2-b]pyridine-3-yl acetic acid.
2001 Sep 1
Optimisation of transgene action at the post-transcriptional level: high quality parthenocarpic fruits in industrial tomatoes.
2002
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery.
2002 Apr
Arabidopsis SHY2/IAA3 inhibits auxin-regulated gene expression.
2002 Feb
An emerging model of auxin transport regulation.
2002 Feb
Organogenesis and terpenoid synthesis in Mentha arvensis.
2002 Feb
Shoot-derived auxin is essential for early lateral root emergence in Arabidopsis seedlings.
2002 Feb
Gravity-stimulated changes in auxin and invertase gene expression in maize pulvinal cells.
2002 Feb
FQR1, a novel primary auxin-response gene, encodes a flavin mononucleotide-binding quinone reductase.
2002 Feb
Analysis of plant hormones in tobacco flowers by micellar electrokinetic capillary chromatography coupled with on-line large volume sample stacking.
2002 Feb 1
Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.
2002 Jan
Arabidopsis cytochrome P450 cyp83B1 mutations activate the tryptophan biosynthetic pathway.
2002 Jan
5-Fluoroindole-3-acetic acid: a prodrug activated by a peroxidase with potential for use in targeted cancer therapy.
2002 Jan 15
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
Delayed abscission and shorter Internodes correlate with a reduction in the ethylene receptor LeETR1 transcript in transgenic tomato.
2002 Mar
Oxic and anoxic enhancement of radiation-mediated toxicity by horseradish peroxidase/indole-3-acetic acid gene therapy.
2002 Mar
Synthesis and bioactivity of C-2 and C-3 methyl ether derivatives of brassinolide.
2002 Mar
Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip.
2002 Mar
Crystal structures of a new class of allosteric effectors complexed to tryptophan synthase.
2002 Mar 22
Patents

Sample Use Guides

As a photosensitizer for the treatment of acne, 0.015% formulation of indoleacetic acid was applied topically.
Route of Administration: Topical
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 Sat Jun 26 03:32:30 UTC 2021
Edited
by admin
on Sat Jun 26 03:32:30 UTC 2021
Record UNII
6U1S09C61L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDOLEACETIC ACID
MI  
Systematic Name English
NSC-3787
Code English
INDOLE-3-ACETIC ACID
Systematic Name English
HETEROAUXIN
Common Name English
INDOLE ACETIC ACID
INCI  
INCI  
Official Name English
INDOLE ACETIC ACID [INCI]
Common Name English
INDOLEACETIC ACID [MI]
Common Name English
1H-INDOLE-3-ACETIC ACID
Systematic Name English
3-(CARBOXYMETHYL)INDOLE
Systematic Name English
IAA
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128915
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
Code System Code Type Description
EPA CompTox
87-51-4
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
DRUG BANK
DB07950
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-748-2
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
FDA UNII
6U1S09C61L
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
MESH
C030737
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
CAS
87-51-4
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
EVMPD
SUB89591
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
MERCK INDEX
M6274
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY Merck Index
PUBCHEM
802
Created by admin on Sat Jun 26 03:32:30 UTC 2021 , Edited by admin on Sat Jun 26 03:32:30 UTC 2021
PRIMARY
WIKIPEDIA
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
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR