U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H9NO2
Molecular Weight 175.184
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOLEACETIC ACID

SMILES

OC(=O)CC1=CNC2=C1C=CC=C2

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 175.184
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
[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
Relationship between production of 3-indoleacetic acid and peroxidase-laccase activities depending on the culture periods in Funalia trogii (Trametes trogii).
2001
Relation between ionic and hormonal regulation of proton pumps in red beet tonoplast.
2001
Biochemical, electron microscopic and immunohistological observations of cationic detergent-extracted cells: detection and improved preservation of microextensions and ultramicroextensions.
2001
Higher plant glycosyltransferases.
2001
Auxin distribution and transport during embryonic pattern formation in wheat.
2001 Apr
Inhibition of beta-amylase activity, starch degradation and sucrose formation by indole-3-acetic acid during banana ripening.
2001 Apr
Characterization of rice anthranilate synthase alpha-subunit genes OASA1 and OASA2. Tryptophan accumulation in transgenic rice expressing a feedback-insensitive mutant of OASA1.
2001 Aug
Oxidative stress, growth factor production and budding in potato tubers during cold storage.
2001 Dec
Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence.
2001 Feb
Exciplex-type behavior and partition of 3-substituted indole derivatives in reverse micelles made with benzylhexadecyldimethylammonium chloride, water and benzene.
2001 Feb
Isolation and 16S rRNA sequence analysis of the beneficial bacteria from the rhizosphere of rice.
2001 Feb
Identification and biochemical characterization of an Arabidopsis indole-3-acetic acid glucosyltransferase.
2001 Feb 9
Developmental regulation of indole-3-acetic acid turnover in Scots pine seedlings.
2001 Jan
Oxidative activation of indole-3-acetic acids to cytotoxic species- a potential new role for plant auxins in cancer therapy.
2001 Jan 15
Mutational analysis of branching in pea. Evidence that Rms1 and Rms5 regulate the same novel signal.
2001 Jul
Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster.
2001 Mar
Flavonoids induced in cells undergoing nodule organogenesis in white clover are regulators of auxin breakdown by peroxidase.
2001 Mar
Auxin-induced elongation of short maize coleoptile segments is supported by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one.
2001 May
Evidence for the presence of DNA-binding proteins involved in regulation of the gene expression of indole-3-pyruvic acid decarboxylase, a key enzyme in indole-3-acetic acid biosynthesis in Azospirillum lipoferum FS.
2001 May
Metabolism of indole-3-acetic acid by orange (Citrus sinensis) flavedo tissue during fruit development.
2001 May
[Oxidation of indole and its derivatives by heme-independent chloroperoxidases].
2001 May-Jun
Auxin promotes gibberellin biosynthesis in decapitated tobacco plants.
2001 Nov
Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine.
2001 Nov
Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase.
2001 Nov 2
Auxin and the power of the proteasome in plants.
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
Roles and activities of Aux/IAA proteins in Arabidopsis.
2001 Sep
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery.
2002 Apr
Shoot-derived auxin is essential for early lateral root emergence in Arabidopsis seedlings.
2002 Feb
Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.
2002 Jan
5-Fluoroindole-3-acetic acid: a prodrug activated by a peroxidase with potential for use in targeted cancer therapy.
2002 Jan 15
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
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 Wed Jul 05 22:36:09 UTC 2023
Edited
by admin
on Wed Jul 05 22:36:09 UTC 2023
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 Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID5020738
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
DRUG BANK
DB07950
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-748-2
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
FDA UNII
6U1S09C61L
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
CHEBI
16411
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
MESH
C030737
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
CAS
87-51-4
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
EVMPD
SUB89591
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
MERCK INDEX
M6274
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY Merck Index
PUBCHEM
802
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
NSC
3787
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
SMS_ID
100000140216
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
ALANWOOD
IAA
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
WIKIPEDIA
Indoleacetic acid
Created by admin on Wed Jul 05 22:36:10 UTC 2023 , Edited by admin on Wed Jul 05 22:36:10 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR