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indole-2-carboxylic acid
2-carboxyindole

Supplier Sponsors

Name:1H-indole-2-carboxylic acid
CAS Number: 1477-50-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:216-030-4
FDA UNII: Search
Nikkaji Web:J132E
Beilstein Number:124132
MDL:MFCD00005611
XlogP3:2.30 (est)
Molecular Weight:161.16019000
Formula:C9 H7 N O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 719.9 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Indole-2-carboxylic acid >98.0%(T)
BST Tianjin Co.
Indole-2-carboxylic acid
EMD Millipore
For experimental / research use only.
Indole-2-carboxylic Acid
sds
Sigma-Aldrich: Aldrich
For experimental / research use only.
Indole-2-carboxylic Acid 98%
sds
TCI AMERICA
For experimental / research use only.
Indole-2-carboxylic Acid >98.0%(GC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for indole-2-carboxylic acid usage levels up to:
 not for fragrance use.
 
Recommendation for indole-2-carboxylic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :72899
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1H-indole-2-carboxylic acid
Chemidplus:0001477505
 
References:
 1H-indole-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1477-50-5
Pubchem (cid):72899
Pubchem (cas):1477-50-5
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB02285
FooDB:FDB022948
Export Tariff Code:2933.99.8210
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ipomoea aquatic
Search Trop Picture
 
Synonyms:
2-carboxyindole
1H-indole-2-carboxylic acid
2-indolecarboxylic acid
 

Articles:

PubMed:Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives.
PubMed:Small molecule Hedgehog pathway antagonists.
PubMed:In Vitro DNA-Binding, Anti-Oxidant and Anticancer Activity of Indole-2-Carboxylic Acid Dinuclear Copper(II) Complexes.
PubMed:Energetics of Radical Formation in Eumelanin Building Blocks: Implications for Understanding Photoprotection Mechanisms in Eumelanin.
PubMed:Fragment-Based Design, Synthesis, and Biological Evaluation of 1-Substituted-indole-2-carboxylic Acids as Selective Mcl-1 Inhibitors.
PubMed:Discovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT1 Selective Antagonists.
PubMed:Indole-2-carboxylic acid derived mono and bis 1,4-disubstituted 1,2,3-triazoles: Synthesis, characterization and evaluation of anticancer, antibacterial, and DNA-cleavage activities.
PubMed:Helicobacter pylori cell binding factor 2: Insights into domain motion.
PubMed:Biased Agonism and Biased Allosteric Modulation at the CB1 Cannabinoid Receptor.
PubMed:Phenolic Compounds from the Leaves of Stewartia pseudocamellia Maxim. and their Whitening Activities.
PubMed:Self-assembly of indole-2-carboxylic acid at graphite and gold surfaces.
PubMed:Pilot dietary intervention with heat-stabilized rice bran modulates stool microbiota and metabolites in healthy adults.
PubMed:Potent and selective small-molecule MCL-1 inhibitors demonstrate on-target cancer cell killing activity as single agents and in combination with ABT-263 (navitoclax).
PubMed:Synthesis of the new ring system bispyrido[4',3':4,5]pyrrolo [1,2-a:1',2'-d]pyrazine and its deaza analogue.
PubMed:Effects of the melanin precursor 5,6-dihydroxy-indole-2-carboxylic acid (DHICA) on DNA damage and repair in the presence of reactive oxygen species.
PubMed:Design, synthesis and biological evaluation of 7-nitro-1H-indole-2-carboxylic acid derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase.
PubMed:Exploratory studies towards various anion recognition chemistry by two different sized cleft shaped organic ligands.
PubMed:Allosteric modulation of a cannabinoid G protein-coupled receptor: binding site elucidation and relationship to G protein signaling.
PubMed:Photophysics of indole-2-carboxylic acid (I2C) and indole-5-carboxylic acid (I5C): heavy atom effect.
PubMed:Inhibitory effects of Korean indigenous plants on tyrosinase and melanogenesis.
PubMed:Light emission from tryptophan oxidation by hypobromous acid.
PubMed:Superoxide reaction with tyrosyl radicals generates para-hydroperoxy and para-hydroxy derivatives of tyrosine.
PubMed:Palladium-catalyzed annulation of allenes with indole-2-carboxylic acid derivatives: synthesis of indolo[2,3-c]pyrane-1-ones via Ar-I reactivity or C-H functionalization.
PubMed:Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.
PubMed:Allosteric modulator ORG27569 induces CB1 cannabinoid receptor high affinity agonist binding state, receptor internalization, and Gi protein-independent ERK1/2 kinase activation.
PubMed:Novel hexahydropyridoindole derivative as prospective agent against oxidative damage in pancreatic β cells.
PubMed:Design and synthesis of novel inhibitors of human kynurenine aminotransferase-I.
PubMed:Photophysics of indole-2-carboxylic acid in an aqueous environment studied by fluorescence spectroscopy in combination with ab initio calculations.
PubMed:Inhibition of glycogen phosphorylation induces changes in cellular proteome and signaling pathways in MIA pancreatic cancer cells.
PubMed:Characterization of N-acetyltryptophan degradation products in concentrated human serum albumin solutions and development of an automated high performance liquid chromatography-mass spectrometry method for their quantitation.
PubMed:I. Novel HCV NS5B polymerase inhibitors: discovery of indole 2-carboxylic acids with C3-heterocycles.
PubMed:Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma.
PubMed:Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs.
PubMed:Parameterization of Org27569: an allosteric modulator of the cannabinoid CB1 G protein-coupled receptor.
PubMed:The discovery and structure-activity relationships of indole-based inhibitors of glutamate carboxypeptidase II.
PubMed:Structural necessity of indole C5-O-substitution of seco-duocarmycin analogs for their cytotoxic activity.
PubMed:Tunable Pd-catalyzed cyclization of indole-2-carboxylic acid allenamides: carboamination vs microwave-assisted hydroamination.
PubMed:Identification and characterization of novel NMDA receptor antagonists selective for NR2A- over NR2B-containing receptors.
PubMed:The tetrahydroisoquinoline derivative SB269,652 is an allosteric antagonist at dopamine D3 and D2 receptors.
PubMed:NW-G01, a novel cyclic hexapeptide antibiotic, produced by Streptomyces alboflavus 313: II. Structural elucidation.
PubMed:Regioselective oxidation of indole- and quinolinecarboxylic acids by cytochrome P450 CYP199A2.
PubMed:Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process.
PubMed:Structure-guided design of alpha-amino acid-derived Pin1 inhibitors.
PubMed:Cellular inhibition of checkpoint kinase 2 (Chk2) and potentiation of camptothecins and radiation by the novel Chk2 inhibitor PV1019 [7-nitro-1H-indole-2-carboxylic acid {4-[1-(guanidinohydrazone)-ethyl]-phenyl}-amide].
PubMed:Conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription. 3: Evaluation and molecular modeling.
PubMed:Functional expression of Francisella tularensis FabH and FabI, potential antibacterial targets.
PubMed:Vibrational spectroscopic studies of indolecarboxylic acids and their metal complexes part VIII. 5-methoxyindole-2-carboxylic acid and its Zn(II) complex.
PubMed:Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles.
PubMed:Effect of dimerization on vibrational spectra of eumelanin precursors.
PubMed:In vitro scavenging activity for reactive oxygen species by N-substituted indole-2-carboxylic acid esters.
PubMed:In vitro and in vivo profile of 5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid benzylmethyl carbamoylamide (dirlotapide), a novel potent MTP inhibitor for obesity.
PubMed:Low-abundance kutznerides from Kutzneria sp. 744.
PubMed:Design, syntheses, biological evaluation, and docking studies of 2-substituted 5-methylsulfonyl-1-phenyl-1H-indoles: potent and selective in vitro cyclooxygenase-2 inhibitors.
PubMed:A chemical genetics approach for the discovery of apoptosis inducers: from phenotypic cell based HTS assay and structure-activity relationship studies, to identification of potential anticancer agents and molecular targets.
PubMed:Spectral and thermal studies of divalent transition metal with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide.
PubMed:Tricyclic quinoxalinediones, aza-kynurenic acids, and indole-2-carboxylic acids as in vivo active NMDA-glycine antagonists.
PubMed:Kutznerides 1-4, depsipeptides from the actinomycete Kutzneria sp. 744 inhabiting mycorrhizal roots of Picea abies seedlings.
PubMed:Synthesis of 6-[2-(benzoxazol-2-ylmethylamino)ethoxy]-1-alkyl-1H-indole-2-carboxylic acid and inhibitory activity on beta-amyloid aggregation.
PubMed:Alkaloids from Portulaca oleracea L.
PubMed:Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARgamma partial agonists.
PubMed:Allosteric modulation of the cannabinoid CB1 receptor.
PubMed:Isolation of three new naturally occurring compounds from the culture of Micromonospora sp. P1068.
PubMed:A-770041, a novel and selective small-molecule inhibitor of Lck, prevents heart allograft rejection.
PubMed:Synthesis and SAR of 2-carboxylic acid indoles as inhibitors of plasminogen activator inhibitor-1.
PubMed:Spectral and thermal studies of divalent transition metal complexes with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide.
PubMed:CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist.
PubMed:Pacemaker activity in hydra is modulated by glycine receptor ligands.
PubMed:The systemic exposure of an N-methyl-D-aspartate receptor antagonist is limited in mice by the P-glycoprotein and breast cancer resistance protein efflux transporters.
PubMed:Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay.
PubMed:Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands.
PubMed:Variations of acidic functions at position 2 and substituents at positions 4, 5 and 6 of the indole moiety and their effect on NMDA-glycine site affinity.
PubMed:A study on the stereochemical purity of trandolapril and octahydro-1H-indole-2-carboxylic acid by HPLC method.
PubMed:Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1. Homology guided site-directed mutagenesis.
PubMed:New versatile route to the synthesis of tetrahydro-beta-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3.
PubMed:KR-31466, a benzopyranylindol analog, attenuates hypoxic injury through mitochondrial K(ATP) channel and protein kinase C activation in heart-derived H9c2 cells.
PubMed:3-(2-carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid: an allosteric inhibitor of fructose-1,6-bisphosphatase at the AMP site.
PubMed:Inhibition by theanine of binding of [3H]AMPA, [3H]kainate, and [3H]MDL 105,519 to glutamate receptors.
PubMed:Tricyclic indole-2-carboxylic acids: highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor.
PubMed:SM-31900, a novel NMDA receptor glycine-binding site antagonist, reduces infarct volume induced by permanent middle cerebral artery occlusion in spontaneously hypertensive rats.
PubMed:In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives.
PubMed:Singlet oxygen-mediated protein oxidation: evidence for the formation of reactive side chain peroxides on tyrosine residues.
PubMed:In vitro and in vivo antagonistic activities of SM-31900 for the NMDA receptor glycine-binding site.
PubMed:The effect of glucose on the potency of two distinct glycogen phosphorylase inhibitors.
PubMed:Identification of nonpeptidic urotensin II receptor antagonists by virtual screening based on a pharmacophore model derived from structure-activity relationships and nuclear magnetic resonance studies on urotensin II.
PubMed:Cooperative binding interactions of glycopeptide antibiotics.
PubMed:Cysteine and indole derivatives as markers for malignant melanoma.
PubMed:GV196771A, an NMDA receptor/glycine site antagonist, attenuates mechanical allodynia in neuropathic rats and reduces tolerance induced by morphine in mice.
PubMed:Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors.
PubMed:Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.
PubMed:Allosteric modulation of [3H]-CGP39653 binding through the glycine site of the NMDA receptor: further studies in rat and human brain.
PubMed:Oxidation of Free Tryptophan and Tryptophan Residues in Peptides and Proteins.
PubMed:Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation.
PubMed:Molecular co-crystals of 2-aminothiazole derivatives.
PubMed:A new allosteric site in glycogen phosphorylase b as a target for drug interactions.
PubMed:Chloptosin, an apoptosis-inducing dimeric cyclohexapeptide produced by Streptomyces.
PubMed:Biodegradation of carbazole by Ralstonia sp. RJGII.123 isolated from a hydrocarbon contaminated soil.
PubMed:Receptor binding characteristics of the novel NMDA receptor glycine site antagonist [3H]GV150526A in rat cerebral cortical membranes.
PubMed:Modulation of nociceptive transmission by NMDA/glycine site receptor in the ventroposterolateral nucleus of the thalamus.
PubMed:Substituted analogues of GV150526 as potent glycine binding site antagonists in animal models of cerebral ischemia.
PubMed:The soluble eumelanin precursor 5,6-dihydroxyindole-2-carboxylic acid enhances oxidative damage in human keratinocyte DNA after UVA irradiation.
PubMed:Expression and characterization of a glycine-binding fragment of the N-methyl-D-aspartate receptor subunit NR1.
PubMed:Cooperation of dopachrome conversion factor with phenoloxidase in the eumelanin pathway in haemolymph of Locusta migratoria (Insecta).
PubMed:Infrared, surface-assisted laser desorption ionization mass spectrometry on frozen aqueous solutions of proteins and peptides using suspensions of organic solids.
PubMed:Enhanced sensitivity of medullary depressor neurons to N-methyl-D-aspartate-glycine site antagonists in the spontaneously hypertensive rat.
PubMed:Possible involvement of ATP-dependent K-channel related mechanisms in the antihypertensive and cough suppressant effects of the novel ACE inhibitor (2S, 3aS, 7aS)-1-(N2-nicotinoyl-L-lysyl-gamma-D-glutamyl)octahydro-1H- indole-2-carboxylic acid.
PubMed:Applications of High-Temperature Aqueous Media for Synthetic Organic Reactions.
PubMed:Novel indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives. Structure-activity relationships for high inhibition of human LDL peroxidation.
PubMed:Pharmacological characterization of MDL 105,519, an NMDA receptor glycine site antagonist.
PubMed:Picolinic acid and indole-2-carboxylic acid: two types of glycinergic compounds modulate motor function differentially.
PubMed:Substituted indole-2-carboxylates as in vivo potent antagonists acting as the strychnine-insensitive glycine binding site.
PubMed:Binding of the radiolabeled glycine site antagonist [3H]MDL 105,519 to homomeric NMDA-NR1a receptors.
PubMed:[3H]MDL 105,519, a high-affinity radioligand for the N-methyl-D-aspartate receptor-associated glycine recognition site.
PubMed:3-(Octadecanoylaminomethyl)indole-2-carboxylic acid derivatives and 1-methyl-3-octadecanoylindole-2-carboxylic acid as inhibitors of cytosolic phospholipase A2.
PubMed:[Chemistry of the cyclic tautomer of tryptophans].
PubMed:Altered responsiveness of medullary depressor neurones to L-glutamate and D-serine in SHR rats.
PubMed:Benzimidazole-type glycine antagonists: the role of the ring nitrogen atoms.
PubMed:Himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus. III. Structural elucidation.
PubMed:Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids.
PubMed:MDL 100,458 and MDL 102,288: two potent and selective glycine receptor antagonists with different functional profiles.
PubMed:Antihypertensive properties of a new long-acting angiotensin converting enzyme inhibitor in renin-dependent and independent hypertensive models.
PubMed:Effects of the excitatory amino acid receptor antagonists kynurenate and indole-2-carboxylic acid on behavioral and neurochemical outcome following experimental brain injury.
PubMed:Regulatory factors for polymerization of melanin monomers within coated vesicles and premelanosomes in melanoma cells.
PubMed:Serum 5-S-cysteinyldopa (5-S-CD) as a marker of melanoma progression.
PubMed:Characterization of indole-2-carboxylate derivatives as antagonists of N-methyl-D-aspartate receptor activity at the associated glycine recognition site.
PubMed:Mechanism of glycine protection in hypoxic injury: analogies with glycine receptor.
PubMed:Competitive antagonism of glutamate receptor channels by substituted benzazepines in cultured cortical neurons.
PubMed:Effects of glycine antagonists on Mg(2+)- and glycine-induced [3H]N-(1-[2-thienyl]cyclohexyl)-3,4-piperidine binding.
PubMed:Spinal pharmacology of thermal hyperesthesia induced by constriction injury of sciatic nerve. Excitatory amino acid antagonists.
PubMed:Specificity of dopachrome tautomerase and inhibition by carboxylated indoles. Considerations on the enzyme active site.
PubMed:Potentiation of ethanol via interference with calcium channels.
PubMed:Induction of estradiol metabolism by dietary indole-3-carbinol in humans.
PubMed:Concentration-jump experiments with NMDA antagonists in mouse cultured hippocampal neurons.
PubMed:Synthesis and angiotensin converting enzyme inhibitory activity of N-carboxymethyldipeptides with omega-(4-piperidyl)alkyl group.
PubMed:Blockade of the glycine modulatory site of NMDA receptors modifies dynorphin-induced behavioral effects.
PubMed:Indole-2-carboxylic acid: a competitive antagonist of potentiation by glycine at the NMDA receptor.
PubMed:Some indolic compounds as markers of the melanocyte activity.
PubMed:Photogeneration of free radicals from eumelanogenic intermediates and metabolites.
PubMed:Effects of thionaphthene 2-carboxylic acid and related compounds on bone resorption in organ culture.
PubMed:CI-906 and CI-907: new orally active nonsulfhydryl angiotensin-converting enzyme inhibitors.
PubMed:Auxin action on proton influx in corn roots and its correlation with growth.
PubMed:A novel synthesis of 2-thioether derivatives of tryptophan. Covalent binding of tryptophan to cysteine sulfhydryl groups in peptides and proteins.
PubMed:Syntheses of monocyclic and bicyclic peptides of tryptathionine and glycine.
PubMed:[Studies on indole derivatives. XII. Reaction of indole-2-carboxylic acid derivatives with carbon disulfide].
PubMed:Mode of action of hypoglycemic agents. 3. Studies on 5-methoxy indole-2-carboxylic acid and quinaldic acid.
PubMed:[STUDIES ON ANTITUMOUR DRUGS. 18. EXPERIMENTAL THERAPY AND TOXICITY OF 5-(BIS-(2-CHLOROETHYL)-AMINO)-INDOLE-2-CARBOXYLIC ACID (AT-346)].
 
Notes:
2-Indolecarboxylic acid is a strong inhibitor of lipid peroxidation, similar to melatonin and some structurally related indole compounds. Lipid peroxidation with tert-butyl hydroperoxide is a source of free radicals (PMID 12236544) 2-Indolecarboxylic acid is a phenolic components known to exist in Korean ginseng (Koryo Insam Hakhoechi (1996), 20(3), 284-290) and brown rice (Han'guk Nonghwa Hakhoechi (1995), 38(5), 478-83). [HMDB]
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