Home Indole and Oxindoles 392-12-1
392-12-1,MFCD00005640
Catalog No.:AA003HWK
392-12-1 | Indole-3-pyruvic acid
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Technical Information
Catalog Number:
AA003HWK
Chemical Name:
Indole-3-pyruvic acid
CAS Number:
392-12-1
Molecular Formula:
C11H9NO3
Molecular Weight:
203.1941
MDL Number:
MFCD00005640
IUPAC Name:
3-(1H-indol-3-yl)-2-oxopropanoic acid
InChI:
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)
InChI Key:
RSTKLPZEZYGQPY-UHFFFAOYSA-N
SMILES:
OC(=O)C(=O)Cc1c[nH]c2c1cccc2
EC Number:
206-874-1
UNII:
4QM0LT13A8
NSC Number:
88874
Properties
Computed Properties
 
Complexity:
277  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
203.058g/mol
Formal Charge:
0
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
203.197g/mol
Monoisotopic Mass:
203.058g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
70.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.3  

Synonyms
 
indol-3-yl pyruvic acid 
indole-3-pyruvic acid 
Indolyl-3-pyruvate 
3-Indolylpyruvic acid; 3-(3-Indolyl)-2-oxopropanoic acid; alpha-Oxo-1H-indole-3-propanoic acid 
3- -2-oxopropanoicacid 
C11H9NO3 
1H-Indole-3-proponoic acid 
CID803 
C11-H9-N-O3 
3-(1H-Indol-3-yl)-2-oxopropanoicacid 
C008122 
3-Indolepyruvic acid 
indol-3-yl pyruvic acid 
3-Indolylpyroracemic acid 
beta-Indolepyruvic acid 
beta-Indolylpyruvic acid 
Indole-3-pyruvic acid monohydrate 
UNII-4QM0LT13A8 
NSC 88874 
3-(indol-3-yl)pyruvic acid 
Indole-3-pyruvic acid 
(Indol-3-yl)pyruvate 
1H-Indole-3-propanoic acid, .alpha.-oxo- 
EINECS 206-874-1 
(indol-3-yl)pyruvic acid 
alpha-Oxo-1H-indole-3-propanoic acid 
BRN 0172966 
1H-Indole-3-propanoic acid, alpha-oxo- 
4QM0LT13A8 
3-(indol-3-yl)pyruvate 
CHEBI:29750 
392-12-1 
RSTKLPZEZYGQPY-UHFFFAOYSA-N 
3-indol-3-yl-2-oxopropanoic acid 
3-[3-Indolyl]-2-oxopropanoic acid 
3IO 
3-(3-Indolyl)-2-oxopropanoic acid 
Indol-3-ylpyruvic acid 
Indole-3-pyrubate 
3-Indolpyruvic acid 
indol-3-pyruvic acid 
PubChem7282 
3-(1H-Indol-3-yl)-2-oxopropanoic acid 
3-indole-pyruvic acid 
35656-49-6 
.beta.-Indolepyruvic acid 
.beta.-Indolylpyruvic acid 
bmse000646 
bmse000685 
1H-Indole-3-pyruvic acid 
DSSTox_CID_22053 
DSSTox_RID_79908 
DSSTox_GSID_42053 
Indole-3-pyruvate 
5-22-06-00324 (Beilstein Handbook Reference) 
MLS000515792 
ARONIS24313 
SCHEMBL125249 
AC1L1A25 
CHEMBL485012 
DTXSID3042053 
CTK4I1112 
HMS2270A21 
EBD45217 
indolepyruvate 
KS-000018CS 
NSC88874 
ZINC1532617 
1H-Indole-3-propanoicacid, a-oxo- 
Tox21_301365 
ANW-46652 
CI-014 
MFCD00005640 
NSC-88874 
SBB003515 
3-Indolylpyruvic acid 
STL286879 
AKOS005267243 
MCULE-1073478615 
VI30400 
NCGC00247042-01 
NCGC00255790-01 
AC-10208 
AJ-26794 
AN-44671 
BC675676 
Indolepyruvic acid 
CAS-392-12-1 
LS-83400 
SMR000112266 
ST056381 
3-(1H-indol-3-yl)-2-keto-propionic acid 
3-(1H-indol-3-yl)-2-oxo-propanoic acid 
AB1011912 
Indole-3-pyruvic acid, >=98.0% (TLC) 
TC-135397 
FT-0627222 
Indole pyruvic acid 
ST24028266 
KS-00004725 
C00331 
I-4200 
1H-Indole-3-propanoic acid, alpha-oxo- (9CI) 
392I121 
3-(1H-indol-3-yl)-2-oxidanylidene-propanoic acid 
AC17FD8D-94BC-4C87-B5E6-D2B60F03B45D 
F9995-2651 
3-(3-Indolyl)-2-oxopropanoic acid; 3-Indolylpyruvic acid 
Literature

Title: Indole derivative production by the root endophyte Piriformospora indica is not required for growth promotion but for biotrophic colonization of barley roots.

Journal: The New phytologist 20121001

Title: Biosynthesis of the halogenated auxin, 4-chloroindole-3-acetic acid.

Journal: Plant physiology 20120701

Title: Plant-derived auxin plays an accessory role in symptom development upon Rhodococcus fascians infection.

Journal: The Plant journal : for cell and molecular biology 20120501

Title: The pathway of auxin biosynthesis in plants.

Journal: Journal of experimental botany 20120501

Title: Translatome and metabolome effects triggered by gibberellins during rosette growth in Arabidopsis.

Journal: Journal of experimental botany 20120401

Title: Auxin biosynthesis: a simple two-step pathway converts tryptophan to indole-3-acetic acid in plants.

Journal: Molecular plant 20120301

Title: PIF4-mediated activation of YUCCA8 expression integrates temperature into the auxin pathway in regulating arabidopsis hypocotyl growth.

Journal: PLoS genetics 20120301

Title: A novel, simple, and sensitive colorimetric method to determine aromatic amino acid aminotransferase activity using the Salkowski reagent.

Journal: Folia microbiologica 20120101

Title: Quorum sensing signaling molecules produced by reference and emerging soft-rot bacteria (Dickeya and Pectobacterium spp.).

Journal: PloS one 20120101

Title: Development and Validation of a Reversed-Phase Liquid Chromatography Method for the Simultaneous Determination of Indole-3-Acetic Acid, Indole-3-Pyruvic Acid, and Abscisic Acid in Barley (Hordeum vulgare L.).

Journal: Journal of analytical methods in chemistry 20120101

Title: A novel tool for studying auxin-metabolism: the inhibition of grapevine indole-3-acetic acid-amido synthetases by a reaction intermediate analogue.

Journal: PloS one 20120101

Title: Protocol: High-throughput and quantitative assays of auxin and auxin precursors from minute tissue samples.

Journal: Plant methods 20120101

Title: Tryptophan in alcoholism treatment I: kynurenine metabolites inhibit the rat liver mitochondrial low Km aldehyde dehydrogenase activity, elevate blood acetaldehyde concentration and induce aversion to alcohol.

Journal: Alcohol and alcoholism (Oxford, Oxfordshire) 20111101

Title: A small-molecule screen identifies L-kynurenine as a competitive inhibitor of TAA1/TAR activity in ethylene-directed auxin biosynthesis and root growth in Arabidopsis.

Journal: The Plant cell 20111101

Title: YUC and TAA1/TAR proteins function in the same pathway for auxin biosynthesis.

Journal: The Plant cell 20111101

Title: The Arabidopsis YUCCA1 flavin monooxygenase functions in the indole-3-pyruvic acid branch of auxin biosynthesis.

Journal: The Plant cell 20111101

Title: Auxin-cytokinin interaction regulates meristem development.

Journal: Molecular plant 20110701

Title: YUCCA6 over-expression demonstrates auxin function in delaying leaf senescence in Arabidopsis thaliana.

Journal: Journal of experimental botany 20110701

Title: Functional characterization of the CKRC1/TAA1 gene and dissection of hormonal actions in the Arabidopsis root.

Journal: The Plant journal : for cell and molecular biology 20110501

Title: Transcriptome analysis of the rhizosphere bacterium Azospirillum brasilense reveals an extensive auxin response.

Journal: Microbial ecology 20110501

Title: Automated analysis of hypocotyl growth dynamics during shade avoidance in Arabidopsis.

Journal: The Plant journal : for cell and molecular biology 20110301

Title: The genetic diversity of culturable nitrogen-fixing bacteria in the rhizosphere of wheat.

Journal: Microbial ecology 20110201

Title: vanishing tassel2 encodes a grass-specific tryptophan aminotransferase required for vegetative and reproductive development in maize.

Journal: The Plant cell 20110201

Title: Arabidopsis and Tobacco superman regulate hormone signalling and mediate cell proliferation and differentiation.

Journal: Journal of experimental botany 20110101

Title: Aintegumenta and Aintegumenta-Like6 regulate auxin-mediated flower development in Arabidopsis.

Journal: BMC research notes 20110101

Title: Genomic insights into the versatility of the plant growth-promoting bacterium Azospirillum amazonense.

Journal: BMC genomics 20110101

Title: Biosynthetic gene cluster for the cladoniamides, bis-indoles with a rearranged scaffold.

Journal: PloS one 20110101

Title: Bioactive pigments from marine bacteria: applications and physiological roles.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Transcriptomic characterization of a synergistic genetic interaction during carpel margin meristem development in Arabidopsis thaliana.

Journal: PloS one 20110101

Title: Tryptophan oxidative metabolism catalyzed by geobacillus stearothermophilus: a thermophile isolated from kuwait soil contaminated with petroleum hydrocarbons.

Journal: International journal of tryptophan research : IJTR 20110101

Title: Insights into auxin signaling in plant-pathogen interactions.

Journal: Frontiers in plant science 20110101

Title: Reassessing the role of N-hydroxytryptamine in auxin biosynthesis.

Journal: Plant physiology 20101201

Title: Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential.

Journal: Journal of microbiology and biotechnology 20101201

Title: 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.

Journal: Molecular plant 20101101

Title: L-Tryptophan catabolism by Rubrivivax benzoatilyticus JA2 occurs through indole 3-pyruvic acid pathway.

Journal: Biodegradation 20100901

Title: Sugar levels regulate tryptophan-dependent auxin biosynthesis in developing maize kernels.

Journal: Plant physiology 20100501

Title: Auxin biosynthesis inhibitors, identified by a genomics-based approach, provide insights into auxin biosynthesis.

Journal: Plant & cell physiology 20100401

Title: Complete genomic structure of the cultivated rice endophyte Azospirillum sp. B510.

Journal: DNA research : an international journal for rapid publication of reports on genes and genomes 20100201

Title: Automatic assignment of EC numbers.

Journal: PLoS computational biology 20100101

Title: Rapid Isocratic Liquid Chromatographic Separation and Quantification of Tryptophan and Six kynurenine Metabolites in Biological Samples with Ultraviolet and Fluorimetric Detection.

Journal: International journal of tryptophan research : IJTR 20100101

Title: Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid.

Journal: Chemical research in toxicology 20091201

Title: D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan.

Journal: Chemical research in toxicology 20091201

Title: High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics.

Journal: Journal of the American Chemical Society 20091104

Title: An anaerobic-type alpha-ketoglutarate ferredoxin oxidoreductase completes the oxidative tricarboxylic acid cycle of Mycobacterium tuberculosis.

Journal: PLoS pathogens 20091101

Title: The TRANSPORT INHIBITOR RESPONSE2 gene is required for auxin synthesis and diverse aspects of plant development.

Journal: Plant physiology 20090901

Title: A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.

Journal: Bioorganic & medicinal chemistry letters 20090901

Title: Regulatory interactions between quorum-sensing, auxin, cytokinin, and the Hrp regulon in relation to gall formation and epiphytic fitness of Pantoea agglomerans pv. gypsophilae.

Journal: Molecular plant-microbe interactions : MPMI 20090701

Title: Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K.

Journal: Journal of medicinal chemistry 20090514

Title: Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.

Journal: The Journal of biological chemistry 20090410

Title: Evolution of camalexin and structurally related indolic compounds.

Journal: Phytochemistry 20090101

Title: CgOpt1, a putative oligopeptide transporter from Colletotrichum gloeosporioides that is involved in responses to auxin and pathogenicity.

Journal: BMC microbiology 20090101

Title: Complete genome sequence of the sugarcane nitrogen-fixing endophyte Gluconacetobacter diazotrophicus Pal5.

Journal: BMC genomics 20090101

Title: Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.

Journal: Journal of the American Chemical Society 20081119

Title: Comprehensive transcriptome analysis of phytohormone biosynthesis and signaling genes in microspore/pollen and tapetum of rice.

Journal: Plant & cell physiology 20081001

Title: The paramutated SULFUREA locus of tomato is involved in auxin biosynthesis.

Journal: Journal of experimental botany 20081001

Title: Functional identification and expression of indole-3-pyruvate decarboxylase from Paenibacillus polymyxa E681.

Journal: Journal of microbiology and biotechnology 20080701

Title: A new path to auxin.

Journal: Nature chemical biology 20080601

Title: An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion.

Journal: Antonie van Leeuwenhoek 20080501

Title: Organization of the ipdC region regulates IAA levels in different Azospirillum brasilense strains: molecular and functional analysis of ipdC in strain SM.

Journal: Environmental microbiology 20080501

Title: 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.

Journal: Molecular plant pathology 20080501

Title: A new gene for auxin synthesis.

Journal: Cell 20080404

Title: Rapid synthesis of auxin via a new tryptophan-dependent pathway is required for shade avoidance in plants.

Journal: Cell 20080404

Title: TAA1-mediated auxin biosynthesis is essential for hormone crosstalk and plant development.

Journal: Cell 20080404

Title: Crystal structure of VioE, a key player in the construction of the molecular skeleton of violacein.

Journal: The Journal of biological chemistry 20080307

Title: A genome survey of Moniliophthora perniciosa gives new insights into Witches' Broom Disease of cacao.

Journal: BMC genomics 20080101

Title: Terrequinone A biosynthesis through L-tryptophan oxidation, dimerization and bisprenylation.

Journal: Nature chemical biology 20070901

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Many roads lead to 'auxin': of nitrilases, synthases, and amidases.

Journal: Plant biology (Stuttgart, Germany) 20060501

Title: Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD.

Journal: Biochemistry 20051206

Title: Aldehyde oxidase (AO) in the root nodules of Lupinus albus and Medicago truncatula: identification of AO in meristematic and infection zones.

Journal: Molecular plant-microbe interactions : MPMI 20050501

Title: 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.

Journal: Biochemistry 20050426

Title: Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection.

Journal: Electrophoresis 20050201

Title: Biochemical and molecular characterization of alpha-ketoisovalerate decarboxylase, an enzyme involved in the formation of aldehydes from amino acids by Lactococcus lactis.

Journal: FEMS microbiology letters 20040915

Title: IAR4, a gene required for auxin conjugate sensitivity in Arabidopsis, encodes a pyruvate dehydrogenase E1alpha homolog.

Journal: Plant physiology 20040601

Title: Aspartate aminotransferase generates proagonists of the aryl hydrocarbon receptor.

Journal: Molecular pharmacology 20030901

Title: Studies on structure-function relationships of indolepyruvate decarboxylase from Enterobacter cloacae, a key enzyme of the indole acetic acid pathway.

Journal: European journal of biochemistry 20030501

Title: The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae.

Journal: The Journal of biological chemistry 20030307

Title: Neurokynurenines (NEKY) as common neurochemical links of stress and anxiety.

Journal: Advances in experimental medicine and biology 20030101

Title: The enol tautomer of indole-3-pyruvic acid as a biological switch in stress responses.

Journal: Advances in experimental medicine and biology 20030101

Title: Formation of kynurenic and xanthurenic acids from kynurenine and 3-hydroxykynurenine in the dinoflagellate Lingulodinium polyedrum: role of a novel, oxidative pathway.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20021101

Title: Evidence for production of the phytohormone indole-3-acetic acid by cyanobacteria.

Journal: Planta 20020601

Title: 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.

Journal: Bioscience, biotechnology, and biochemistry 20010501

Title: [Aerobic methylobacteria are capable of synthesizing auxins].

Journal: Mikrobiologiia 20010101

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