ChemFOnt: Showing chemical card for Indole-3-propionic acid (CFc000001551)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:12 UTC

Chemfont ID

CFc000001551

Molecule Identification

Common Name

Indole-3-propionic acid

Definition

Indole-3-propionic acid (IPA, indole-3-propionate, or indole propionic acid), is a reductive product of tryptophan formed by bacteria in the gastrointestinal tract of mammals and birds (PMID:29168502 ). It is endogenously produced by human microbiota and has only been detected in vivo (PMID:19234110 ). While many microbial metabolites produced in the gut are toxic or act as uremic toxins (when they are reabsorbed through the gut epithelia), indole-3-propionic acid is a very beneficial microbial metabolite (PMID:30914514 , 30862081 , 29238104 ). In limited studies, urinary IPA correlates positively with disease and it remains unclear if this represents host bacteria responding to pathology via the production of IPA, or intestinal permeability changes leading to higher absorption and excretion of IPA, or inflammatory changes within kidneys leading to high excretion of IPA (PMID:32132996 ). Indole-3-propionic acid is a remarkably strong antioxidant (PMID:10721080 ). It is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals synthesized by the human body. Similar to melatonin but unlike other antioxidants, indole-3-propionic acid scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds (PMID:9928448 , 10419516 ). Indole-3-propionic acid has been shown to prevent oxidative stress and the death of primary neurons and neuroblastoma cells exposed to the amyloid beta-protein in the form of amyloid fibrils, one of the most prominent neuropathologic features of Alzheimer's disease. 3-Indolepropionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress. (PMID 10419516 ) More recently it has been found that higher indole-3-propionic acid levels in serum/plasma are associated with a reduced likelihood of type 2 diabetes and with higher levels of consumption of fibre-rich foods (PMID:28397877 ). Studies have shown that serum levels of indole-3-propionic acid are positively correlated with dietary fibre intake and negatively correlated with C-reactive protein levels (PMID:29795366 ). Indole-3-propionic acid is a marker for the presence of Clostridium sporogenes in the gut. Higher levels are associated with higher levels of Clostridium sporogenes (PMID:7378938 ). In addition to its useful physiological role in mammals, indole-3-propionic acid is a plant hormone with functions similar to indole-3-acetic acid (or IAA), the major plant auxin. Recent studies have shed some light on additional mechanisms of action of IPA. In the intestine, IPA could serve as a ligand to an adopted orphan nuclear receptor, Pregnane X receptor (PXR) and act as an anti-inflammatory agent (PMID:25065623 ). This property has allowed investigators to develop more potent analogs targeting PXR (PMID:32153125 ). Other tissues may also be targeted by IPA in a similar manner (PMID:31211619 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-(3-Indolyl)propionic acid	ChEBI
Indolepropionic acid	ChEBI
b-(3-Indolyl)propionate	Generator
b-(3-Indolyl)propionic acid	Generator
beta-(3-Indolyl)propionate	Generator
Β-(3-indolyl)propionate	Generator
Β-(3-indolyl)propionic acid	Generator
Indolepropionate	Generator
Indole-3-propionate	Generator
Indole propionate	MeSH
Indole-3-propanoic acid	MeSH
Indole-3-propionic acid	ChEBI
3-Indolepropionate	Generator, HMDB
1H-Indole-3-propionate	HMDB
1H-Indole-3-propionic acid	HMDB
3-(1H-indol-3-yl)Propanoate	HMDB, Generator
3-(1H-Indol-3-yl)propanoic acid	HMDB
3-(1H-indol-3-yl)Propionate	HMDB
3-(1H-Indol-3-yl)propionic acid	HMDB
3-(2-Carboxyethyl)-1H-indole	HMDB
3-(3-Indolyl)propanoate	HMDB
3-(3-Indolyl)propanoic acid	HMDB
3-(3-Indolyl)propionate	HMDB
3-(3-Indolyl)propionic acid	HMDB
b-Indole-3-propionate	HMDB
b-Indole-3-propionic acid	HMDB
b-Indolepropionate	HMDB
b-Indolepropionic acid	HMDB
beta-Indole-3-propionate	HMDB
beta-Indole-3-propionic acid	HMDB
beta-Indolepropionate	HMDB
beta-Indolepropionic acid	HMDB
IPA	HMDB
3-Indolepropionic acid	HMDB
1H-Indole-3-propanoic acid	HMDB
3-(Indole-3-yl)propanoic acid	HMDB
3-(Indole-3-yl)propionic acid	HMDB
beta-(3-Indolyl)propanoic acid	HMDB
beta-Indole-3-propanoic acid	HMDB
beta-Indolepropanoic acid	HMDB
β-(3-Indolyl)propanoic acid	HMDB
β-Indole-3-propanoic acid	HMDB
β-Indole-3-propionic acid	HMDB
β-Indolepropanoic acid	HMDB
β-Indolepropionic acid	HMDB

Chemical Formula

C₁₁H₁₁NO₂

Average Molecular Weight

189.2105

Monoisotopic Molecular Weight

189.078978601

IUPAC Name

3-(1H-indol-3-yl)propanoic acid

Traditional Name

indolylpropionic acid

CAS Registry Number

830-96-6

SMILES

OC(=O)CCC1=CNC2=C1C=CC=C2

InChI Identifier

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)

InChI Key

GOLXRNDWAUTYKT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid (CHEBI:43580 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14606996)
Saliva (PMID: 21190195)

Cellular substructure

Membrane (HMDB: HMDB0002302)
Cell membrane (HMDB: HMDB0002302)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)
Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002302)

Source

Exogenous

Exogenous (HMDB: HMDB0002302)

Food

Food (HMDB: HMDB0002302)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Endogenous

Endogenous (HMDB: HMDB0002302)

Plant

Fabaceae (HMDB: HMDB0002302)

Microbe

Microbe (HMDB: HMDB0002302)
Clostridium sporogenes (HMDB: HMDB0002302)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002302)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.15	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.05 m³·mol⁻¹	ChemAxon
Polarizability	20 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon