U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of 3-INDOLEPROPIONIC ACID

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)

HIDE SMILES / InChI

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.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Degradation of tryptophan and related indolic compounds by ruminal bacteria, protozoa and their mixture in vitro.
2003
Effects of phthalic anhydride modification on horseradish peroxidase stability and activity.
2003 Jan 20
Determination of phytohormones of environmental impact by capillary zone electrophoresis.
2004 Mar 24
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Mass spectrometry-based screening for inhibitors of beta-amyloid protein aggregation.
2005 Nov 1
Evaluation of indole-based probes for high-throughput screening of drug binding to human serum albumin: Analysis by high-performance affinity chromatography.
2009 Apr
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
Organic cadmium complexes as proteasome inhibitors and apoptosis inducers in human breast cancer cells.
2013 Jun
Patents

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 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
by admin
on Fri Dec 15 19:35:16 UTC 2023
Edited
by admin
on Fri Dec 15 19:35:16 UTC 2023
Record UNII
JF49U1Q7KN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-INDOLEPROPIONIC ACID
Systematic Name English
VP-20629
Code English
NSC-47831
Code English
OXIGON
Brand Name English
SHP622
Code English
VP20629
Code English
3-(INDOL-3-YL)PROPIONIC ACID
Systematic Name English
SHP-622
Code English
NSC-3252
Code English
Code System Code Type Description
PUBCHEM
3744
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
NSC
47831
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
CAS
830-96-6
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
NSC
3252
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
WIKIPEDIA
3-Indolepropionic acid
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-600-1
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
DRUG BANK
DB02758
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
FDA UNII
JF49U1Q7KN
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID7061192
Created by admin on Fri Dec 15 19:35:16 UTC 2023 , Edited by admin on Fri Dec 15 19:35:16 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY