NP-MRD: Showing NP-Card for Indole-3-propionic acid (NP0000531)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:47 UTC

Updated at

2025-02-11 15:48:23 UTC

NP-MRD ID

NP0000531

Natural Product DOI

https://doi.org/10.57994/2819

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indole-3-propionic acid

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652302242018262D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3325 9998.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.0469 9999.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000531

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C11H11NO2

> <MOLECULAR_WEIGHT>
189.2105

> <EXACT_MASS>
189.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.00041471857803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.154324763333333

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.175193522886932

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8029322038078455

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
53.05310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indolylpropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.1548664.625   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8669.1548663.085   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.4888665.395   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

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
3-Indolepropionate	HMDB
1H-Indole-3-propionate	HMDB
1H-Indole-3-propionic acid	HMDB
3-(1H-indol-3-yl)Propanoate	HMDB
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
Indole propionate	HMDB
Indole-3-propanoic acid	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
Indole-3-propionic acid	ChEBI

Chemical Formula

C₁₁H₁₁NO₂

Average Mass

189.2105 Da

Monoisotopic Mass

189.07898 Da

IUPAC Name

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

Traditional Name

indolylpropionic acid

CAS Registry Number

830-96-6

SMILES

OC(=O)CCC1=CNC2=CC=CC=C12

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-13	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cucurbita pepo	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pisum sativum	KNApSAcK Database	22123792
Scheffersomyces spartinae	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	134 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.75	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

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

External Links

HMDB ID

HMDB0002302

DrugBank ID

DB02758

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000941

KNApSAcK ID

C00000115

Chemspider ID

3613

KEGG Compound ID

Not Available

BioCyc ID

INDOLE-PROPIONATE

BiGG ID

Not Available

Wikipedia Link

3-Indolepropionic acid

METLIN ID

6602

PubChem Compound

3744

PDB ID

Not Available

ChEBI ID

43580

Good Scents ID

Not Available

References

General References

Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA: Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid. J Biol Chem. 1999 Jul 30;274(31):21937-42. [PubMed:10419516 ]
Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, Siuzdak G: Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3698-703. doi: 10.1073/pnas.0812874106. Epub 2009 Feb 20. [PubMed:19234110 ]
de Mello VD, Paananen J, Lindstrom J, Lankinen MA, Shi L, Kuusisto J, Pihlajamaki J, Auriola S, Lehtonen M, Rolandsson O, Bergdahl IA, Nordin E, Ilanne-Parikka P, Keinanen-Kiukaanniemi S, Landberg R, Eriksson JG, Tuomilehto J, Hanhineva K, Uusitupa M: Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study. Sci Rep. 2017 Apr 11;7:46337. doi: 10.1038/srep46337. [PubMed:28397877 ]
Negatu DA, Yamada Y, Xi Y, Go ML, Zimmerman M, Ganapathy U, Dartois V, Gengenbacher M, Dick T: Gut Microbiota Metabolite Indole Propionic Acid Targets Tryptophan Biosynthesis in Mycobacterium tuberculosis. mBio. 2019 Mar 26;10(2). pii: mBio.02781-18. doi: 10.1128/mBio.02781-18. [PubMed:30914514 ]
Konopelski P, Konop M, Gawrys-Kopczynska M, Podsadni P, Szczepanska A, Ufnal M: Indole-3-Propionic Acid, a Tryptophan-Derived Bacterial Metabolite, Reduces Weight Gain in Rats. Nutrients. 2019 Mar 11;11(3). pii: nu11030591. doi: 10.3390/nu11030591. [PubMed:30862081 ]
Yisireyili M, Takeshita K, Saito S, Murohara T, Niwa T: Indole-3-propionic acid suppresses indoxyl sulfate-induced expression of fibrotic and inflammatory genes in proximal tubular cells. Nagoya J Med Sci. 2017 Nov;79(4):477-486. doi: 10.18999/nagjms.79.4.477. [PubMed:29238104 ]
Tuomainen M, Lindstrom J, Lehtonen M, Auriola S, Pihlajamaki J, Peltonen M, Tuomilehto J, Uusitupa M, de Mello VD, Hanhineva K: Associations of serum indolepropionic acid, a gut microbiota metabolite, with type 2 diabetes and low-grade inflammation in high-risk individuals. Nutr Diabetes. 2018 May 25;8(1):35. doi: 10.1038/s41387-018-0046-9. [PubMed:29795366 ]
Jellet JJ, Forrest TP, Macdonald IA, Marrie TJ, Holdeman LV: Production of indole-3-propanoic acid and 3-(p-hydroxyphenyl)propanoic acid by Clostridium sporogenes: a convenient thin-layer chromatography detection system. Can J Microbiol. 1980 Apr;26(4):448-53. doi: 10.1139/m80-074. [PubMed:7378938 ]
Venkatesh M, Mukherjee S, Wang H, Li H, Sun K, Benechet AP, Qiu Z, Maher L, Redinbo MR, Phillips RS, Fleet JC, Kortagere S, Mukherjee P, Fasano A, Le Ven J, Nicholson JK, Dumas ME, Khanna KM, Mani S: Symbiotic bacterial metabolites regulate gastrointestinal barrier function via the xenobiotic sensor PXR and Toll-like receptor 4. Immunity. 2014 Aug 21;41(2):296-310. doi: 10.1016/j.immuni.2014.06.014. Epub 2014 Jul 24. [PubMed:25065623 ]
Pulakazhi Venu VK, Saifeddine M, Mihara K, Tsai YC, Nieves K, Alston L, Mani S, McCoy KD, Hollenberg MD, Hirota SA: The pregnane X receptor and its microbiota-derived ligand indole 3-propionic acid regulate endothelium-dependent vasodilation. Am J Physiol Endocrinol Metab. 2019 Aug 1;317(2):E350-E361. doi: 10.1152/ajpendo.00572.2018. Epub 2019 Jun 18. [PubMed:31211619 ]

Showing NP-Card for Indole-3-propionic acid (NP0000531)

MOL for NP0000531 (Indole-3-propionic acid)

3D MOL for NP0000531 (Indole-3-propionic acid)

3D SDF for NP0000531 (Indole-3-propionic acid)

3D-SDF for NP0000531 (Indole-3-propionic acid)

PDB for NP0000531 (Indole-3-propionic acid)

3D PDB for NP0000531 (Indole-3-propionic acid)

SMILES for NP0000531 (Indole-3-propionic acid)

INCHI for NP0000531 (Indole-3-propionic acid)

Structure for NP0000531 (Indole-3-propionic acid)

3D Structure for NP0000531 (Indole-3-propionic acid)