INDOLE-3-PYRUVIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H9NO3
Molecular Weight	203.1941
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RSTKLPZEZYGQPY-UHFFFAOYSA-N

InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
[Aerobic methylobacteria are capable of synthesizing auxins].	2001 Jul-Aug	11558269
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	11440156
Evidence for production of the phytohormone indole-3-acetic acid by cyanobacteria.	2002 Jun	12029472
Formation of kynurenic and xanthurenic acids from kynurenine and 3-hydroxykynurenine in the dinoflagellate Lingulodinium polyedrum: role of a novel, oxidative pathway.	2002 Nov	12379423
The enol tautomer of indole-3-pyruvic acid as a biological switch in stress responses.	2003	15206779
Neurokynurenines (NEKY) as common neurochemical links of stress and anxiety.	2003	15206724
The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae.	2003 Mar 7	12499363
Studies on structure-function relationships of indolepyruvate decarboxylase from Enterobacter cloacae, a key enzyme of the indole acetic acid pathway.	2003 May	12752452
Aspartate aminotransferase generates proagonists of the aryl hydrocarbon receptor.	2003 Sep	12920190
IAR4, a gene required for auxin conjugate sensitivity in Arabidopsis, encodes a pyruvate dehydrogenase E1alpha homolog.	2004 Jun	15173569
Biochemical and molecular characterization of alpha-ketoisovalerate decarboxylase, an enzyme involved in the formation of aldehydes from amino acids by Lactococcus lactis.	2004 Sep 15	15358422
Intermediates and transition states in thiamin diphosphate-dependent decarboxylases. A kinetic and NMR study on wild-type indolepyruvate decarboxylase and variants using indolepyruvate, benzoylformate, and pyruvate as substrates.	2005 Apr 26	15835904
Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD.	2005 Dec 6	16313168
Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection.	2005 Feb	15714546
Aldehyde oxidase (AO) in the root nodules of Lupinus albus and Medicago truncatula: identification of AO in meristematic and infection zones.	2005 May	15915639
Many roads lead to "auxin": of nitrilases, synthases, and amidases.	2006 May	16807824
The paramutated SULFUREA locus of tomato is involved in auxin biosynthesis.	2008	18757490
TAA1-mediated auxin biosynthesis is essential for hormone crosstalk and plant development.	2008 Apr 4	18394997
Rapid synthesis of auxin via a new tryptophan-dependent pathway is required for shade avoidance in plants.	2008 Apr 4	18394996
A new gene for auxin synthesis.	2008 Apr 4	18394986
Functional identification and expression of indole-3-pyruvate decarboxylase from Paenibacillus polymyxa E681.	2008 Jul	18667851
A new path to auxin.	2008 Jun	18488010
Crystal structure of VioE, a key player in the construction of the molecular skeleton of violacein.	2008 Mar 7	18171677
Indole-3-acetic acid (IAA) biosynthesis in the smut fungus Ustilago maydis and its relevance for increased IAA levels in infected tissue and host tumour formation.	2008 May	18705875
Organization of the ipdC region regulates IAA levels in different Azospirillum brasilense strains: molecular and functional analysis of ipdC in strain SM.	2008 May	18248455
An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion.	2008 May	17952626
A genome survey of Moniliophthora perniciosa gives new insights into Witches' Broom Disease of cacao.	2008 Nov 18	19019209
Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.	2008 Nov 19	18954141
Comprehensive transcriptome analysis of phytohormone biosynthesis and signaling genes in microspore/pollen and tapetum of rice.	2008 Oct	18718932
Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.	2009 Apr 10	19189963
CgOpt1, a putative oligopeptide transporter from Colletotrichum gloeosporioides that is involved in responses to auxin and pathogenicity.	2009 Aug 21	19698103
D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan.	2009 Dec	19860415
Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid.	2009 Dec	19860413
Regulatory interactions between quorum-sensing, auxin, cytokinin, and the Hrp regulon in relation to gall formation and epiphytic fitness of Pantoea agglomerans pv. gypsophilae.	2009 Jul	19522567
An anaerobic-type alpha-ketoglutarate ferredoxin oxidoreductase completes the oxidative tricarboxylic acid cycle of Mycobacterium tuberculosis.	2009 Nov	19936047
High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics.	2009 Nov 4	19824661
Evolution of camalexin and structurally related indolic compounds.	2009 Oct-Nov	19523656
The TRANSPORT INHIBITOR RESPONSE2 gene is required for auxin synthesis and diverse aspects of plant development.	2009 Sep	19625638
Complete genome sequence of the sugarcane nitrogen-fixing endophyte Gluconacetobacter diazotrophicus Pal5.	2009 Sep 23	19775431
Rapid Isocratic Liquid Chromatographic Separation and Quantification of Tryptophan and Six kynurenine Metabolites in Biological Samples with Ultraviolet and Fluorimetric Detection.	2010	22084598
Auxin biosynthesis inhibitors, identified by a genomics-based approach, provide insights into auxin biosynthesis.	2010 Apr	20234049
Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential.	2010 Dec	21193830
Reassessing the role of N-hydroxytryptamine in auxin biosynthesis.	2010 Dec	20974893
Complete genomic structure of the cultivated rice endophyte Azospirillum sp. B510.	2010 Feb	20047946
Automatic assignment of EC numbers.	2010 Jan 29	20126531
Sugar levels regulate tryptophan-dependent auxin biosynthesis in developing maize kernels.	2010 May	20237017
Sugar-hormone cross-talk in seed development: two redundant pathways of IAA biosynthesis are regulated differentially in the invertase-deficient miniature1 (mn1) seed mutant in maize.	2010 Nov	20924026
L-Tryptophan catabolism by Rubrivivax benzoatilyticus JA2 occurs through indole 3-pyruvic acid pathway.	2010 Sep	20217460

Patents

Name

Type

Language

INDOLE-3-PYRUVIC ACID

Systematic Name

English

1H-INDOLE-3-PROPANOIC ACID, ALPHA-OXO-

Common Name

English

KETO TRYPTOPHAN

Systematic Name

English

1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-OXO

Systematic Name

English

NSC-88874

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

226700