Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H11NO2 |
| Molecular Weight | 189.2105 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC1=CNC2=C1C=CC=C2
InChI
InChIKey=GOLXRNDWAUTYKT-UHFFFAOYSA-N
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
| Molecular Formula | C11H11NO2 |
| Molecular Weight | 189.2105 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
3-Indolepropionic acid (IN-OX1; Indole-3-propionic acid; OX-1; Oxigon; SHP 22; SHP-622; VP-20629), an endogenous substance produced by bacteria in the intestine, is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland. 3-Indolepropionic acid is being studied for therapeutic use in Alzheimer's disease. 3-Indolepropionic acid (IPA) completely protected primary neurons and neuroblastoma cells against oxidative damage and death caused by exposure to Abeta, by inhibition of superoxide dismutase, or by treatment with hydrogen peroxide. In kinetic competition experiments using free radical-trapping agents, the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin, an indoleamine considered to be the most potent naturally occurring scavenger of free radicals. In contrast with other antioxidants, IPA was not converted to reactive intermediates with pro-oxidant activity. In 2011, Intellect redirected the focus of the OX1 program from Alzheimer's disease to FA (Friedreich's Ataxia). Research suggests that the symptoms associated with FA are the result of oxidative stress caused by the abnormal accumulation of iron. OX1's ability to neutralize ROS could be an effective agent to reduce oxidative stress in FA, thereby eliminating the symptoms of FA and increasing both quality of life and longevity in affected individuals.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Organic cadmium complexes as proteasome inhibitors and apoptosis inducers in human breast cancer cells. | 2013-06 |
|
| Clinical aspects of melatonin intervention in Alzheimer's disease progression. | 2010-09 |
|
| Comprehensive feature analysis for sample classification with comprehensive two-dimensional LC. | 2010-06 |
|
| A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan. | 2010-04-21 |
|
| Melatonin restores the basal level of lipid peroxidation in rat tissues exposed to potassium bromate in vitro. | 2010 |
|
| [Metabonomic profiling of plasma metabolites in Wistar rats to study the effect of aging by means of GC/TOFMS-based techniques]. | 2009-10 |
|
| Auxin amidohydrolases from Brassica rapa cleave the alanine conjugate of indolepropionic acid as a preferable substrate: a biochemical and modeling approach. | 2009-09 |
|
| Indole-3-propionic acid attenuates neuronal damage and oxidative stress in the ischemic hippocampus. | 2009-07 |
|
| Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K. | 2009-05-14 |
|
| Evaluation of indole-based probes for high-throughput screening of drug binding to human serum albumin: Analysis by high-performance affinity chromatography. | 2009-04 |
|
| [Relationship between toxic effects of potassium bromate and endocrine glands]. | 2009-02-19 |
|
| Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines. | 2009 |
|
| Syntheses of IAA- and IPA-amino acid conjugates. | 2008-11-21 |
|
| Identification and quantitation of auxins in plants by liquid chromatography/electrospray ionization ion trap mass spectrometry. | 2008-08 |
|
| The tryptophan aminotransferase Tam1 catalyses the single biosynthetic step for tryptophan-dependent pigment synthesis in Ustilago maydis. | 2008-04 |
|
| Analytical method for beta-amyloid fibrils using CE-laser induced fluorescence and its application to screening for inhibitors of beta-amyloid protein aggregation. | 2007-07-01 |
|
| Binding behavior of amino acid conjugates of indole-3-acetic acid to immobilized human serum albumin. | 2007-06-22 |
|
| Mutation of E1-CONJUGATING ENZYME-RELATED1 decreases RELATED TO UBIQUITIN conjugation and alters auxin response and development. | 2007-06 |
|
| Multicomponent synthesis of 3-indolepropionic acids. | 2007-01-18 |
|
| Structure-based design of indole propionic acids as novel PPARalpha/gamma co-agonists. | 2006-08-01 |
|
| Production of indolic compounds by rumen bacteria isolated from grazing ruminants. | 2006-06 |
|
| Melatonin in Alzheimer's disease and other neurodegenerative disorders. | 2006-05-04 |
|
| Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: a new class of protective agents. | 2006-05-04 |
|
| Laser probes of conformational isomerization in flexible molecules and complexes. | 2006-03-30 |
|
| On the energy landscapes of 3-indole acetic acid and 3-indole propionic acid. A study of side chain flexibilities in their S(0) and S(1) electronic states. | 2006-03-07 |
|
| Protective effects of melatonin and indole-3-propionic acid against lipid peroxidation, caused by potassium bromate in the rat kidney. | 2006-01-07 |
|
| Lanthanide(III) and Yttrium(III) Complexes of Benzimidazole-2-Acetic Acid: Synthesis, Characterisation and Effect of La(III) Complex on Germination of Wheat. | 2006 |
|
| Mass spectrometry-based screening for inhibitors of beta-amyloid protein aggregation. | 2005-11-01 |
|
| Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1. | 2005-09 |
|
| Direct measurement of the energy thresholds to conformational isomerization. II. 3-indole-propionic acid and its water-containing complex. | 2005-06-01 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Comparison of potential protective effects of melatonin, indole-3-propionic acid, and propylthiouracil against lipid peroxidation caused by potassium bromate in the thyroid gland. | 2005-05-01 |
|
| A novel auxin conjugate hydrolase from wheat with substrate specificity for longer side-chain auxin amide conjugates. | 2004-08 |
|
| Determination of phytohormones of environmental impact by capillary zone electrophoresis. | 2004-03-24 |
|
| Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004-03 |
|
| A liquid chromatographic-tandem mass spectrometric method for the analysis of serotonin and related indoles in human whole blood. | 2003-10 |
|
| Increased tryptophan decarboxylase and monoamine oxidase activities induce Sekiguchi lesion formation in rice infected with Magnaporthe grisea. | 2003-10 |
|
| Metabolic profiling of root exudates of Arabidopsis thaliana. | 2003-04-23 |
|
| Effects of phthalic anhydride modification on horseradish peroxidase stability and activity. | 2003-01-20 |
|
| Degradation of tryptophan and related indolic compounds by ruminal bacteria, protozoa and their mixture in vitro. | 2003 |
|
| Amelioration of hepatic ischemia/reperfusion injury using indolepropionic acid. | 2002-12 |
|
| Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease. | 2002-09-06 |
|
| In vitro organogenesis and genetic transformation in popular Cucumis sativus L. through Agrobacterium tumefaciens. | 2002-03 |
|
| The role of water bridges in directing the conformational preferences of 3-indole-propionic acid and tryptamine. | 2001-06-13 |
|
| Comparison of the protective effect of melatonin with other antioxidants in the hamster kidney model of estradiol-induced DNA damage. | 2001-03-01 |
|
| Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli. | 2001-02-06 |
|
| Carcinogen-induced, free radical-mediated reduction in microsomal membrane fluidity: reversal by indole-3-propionic acid. | 2001-02 |
|
| Relative efficacies of indole antioxidants in reducing autoxidation and iron-induced lipid peroxidation in hamster testes. | 2001 |
|
| Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction. | 2001 |
Sample Use Guides
Friedreich's Ataxia treatment: subjects will receive multiple doses of 3-Indolepropionic acid (VP 20629) (300 mg, 600 mg, or 900 mg total daily dose) or placebo. VP20629 or placebo will be administered every 8 hours for 7 days with a single morning dose on Day 8.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10419516
In the primary rat hippocampal cultures evaluated by bodipy green fluorescence, 1uM Abeta treatment resulted in almost complete reduction of cell fluorescence as compared with untreated cells. In these
experiments, similar concentrations (1 uM) of 3-Indolepropionic acid (IPA) or melatonin
added to Abeta-containing media were sufficient to provide full
protection from the neurotoxic effects of Abeta, as evidenced by
levels of fluorescence comparable to control primary neurons.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
JF49U1Q7KN
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| Record Status |
Validated (UNII)
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