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)
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 |
---|---|---|
Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease. | 2002 Aug-Oct |
|
Amelioration of hepatic ischemia/reperfusion injury using indolepropionic acid. | 2002 Dec |
|
Degradation of tryptophan and related indolic compounds by ruminal bacteria, protozoa and their mixture in vitro. | 2003 |
|
Metabolic profiling of root exudates of Arabidopsis thaliana. | 2003 Apr 23 |
|
Effects of phthalic anhydride modification on horseradish peroxidase stability and activity. | 2003 Jan 20 |
|
A liquid chromatographic-tandem mass spectrometric method for the analysis of serotonin and related indoles in human whole blood. | 2003 Oct |
|
Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004 Mar |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Direct measurement of the energy thresholds to conformational isomerization. II. 3-indole-propionic acid and its water-containing complex. | 2005 Jun 1 |
|
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 May 1 |
|
Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1. | 2005 Sep |
|
Lanthanide(III) and Yttrium(III) Complexes of Benzimidazole-2-Acetic Acid: Synthesis, Characterisation and Effect of La(III) Complex on Germination of Wheat. | 2006 |
|
Structure-based design of indole propionic acids as novel PPARalpha/gamma co-agonists. | 2006 Aug 1 |
|
Production of indolic compounds by rumen bacteria isolated from grazing ruminants. | 2006 Jun |
|
Laser probes of conformational isomerization in flexible molecules and complexes. | 2006 Mar 30 |
|
Melatonin in Alzheimer's disease and other neurodegenerative disorders. | 2006 May 4 |
|
Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: a new class of protective agents. | 2006 May 4 |
|
Protective effects of melatonin and indole-3-propionic acid against lipid peroxidation, caused by potassium bromate in the rat kidney. | 2006 Nov-Dec |
|
Multicomponent synthesis of 3-indolepropionic acids. | 2007 Jan 18 |
|
Analytical method for beta-amyloid fibrils using CE-laser induced fluorescence and its application to screening for inhibitors of beta-amyloid protein aggregation. | 2007 Jul 1 |
|
Mutation of E1-CONJUGATING ENZYME-RELATED1 decreases RELATED TO UBIQUITIN conjugation and alters auxin response and development. | 2007 Jun |
|
Binding behavior of amino acid conjugates of indole-3-acetic acid to immobilized human serum albumin. | 2007 Jun 22 |
|
The tryptophan aminotransferase Tam1 catalyses the single biosynthetic step for tryptophan-dependent pigment synthesis in Ustilago maydis. | 2008 Apr |
|
Identification and quantitation of auxins in plants by liquid chromatography/electrospray ionization ion trap mass spectrometry. | 2008 Aug |
|
Evaluation of indole-based probes for high-throughput screening of drug binding to human serum albumin: Analysis by high-performance affinity chromatography. | 2009 Apr |
|
Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K. | 2009 May 14 |
|
[Metabonomic profiling of plasma metabolites in Wistar rats to study the effect of aging by means of GC/TOFMS-based techniques]. | 2009 Oct |
|
Auxin amidohydrolases from Brassica rapa cleave the alanine conjugate of indolepropionic acid as a preferable substrate: a biochemical and modeling approach. | 2009 Sep |
|
Melatonin restores the basal level of lipid peroxidation in rat tissues exposed to potassium bromate in vitro. | 2010 |
|
A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan. | 2010 Apr 21 |
|
Comprehensive feature analysis for sample classification with comprehensive two-dimensional LC. | 2010 Jun |
|
Clinical aspects of melatonin intervention in Alzheimer's disease progression. | 2010 Sep |
|
Organic cadmium complexes as proteasome inhibitors and apoptosis inducers in human breast cancer cells. | 2013 Jun |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
3744
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
47831
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
830-96-6
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
3252
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
3-Indolepropionic acid
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
212-600-1
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
DB02758
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
JF49U1Q7KN
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY | |||
|
DTXSID7061192
Created by
admin on Fri Dec 15 19:35:16 GMT 2023 , Edited by admin on Fri Dec 15 19:35:16 GMT 2023
|
PRIMARY |
ACTIVE MOIETY