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Record Information
Created at2006-05-22 14:17:47 UTC
Updated at2021-10-07 20:40:47 UTC
NP-MRD IDNP0000531
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndole-3-propionic acid
DescriptionIndole-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 ).
beta-(3-Indolyl)propionic acidChEBI
Indolepropionic acidChEBI
b-(3-Indolyl)propionic acidGenerator
Β-(3-indolyl)propionic acidGenerator
1H-Indole-3-propionic acidHMDB
3-(1H-indol-3-yl)Propanoic acidHMDB
3-(1H-indol-3-yl)Propionic acidHMDB
3-(3-Indolyl)propanoic acidHMDB
3-(3-Indolyl)propionic acidHMDB
b-Indole-3-propionic acidHMDB
b-Indolepropionic acidHMDB
beta-Indole-3-propionic acidHMDB
beta-Indolepropionic acidHMDB
Indole propionateHMDB
Indole-3-propanoic acidHMDB
3-Indolepropionic acidHMDB
1H-Indole-3-propanoic acidHMDB
3-(Indole-3-yl)propanoic acidHMDB
3-(Indole-3-yl)propionic acidHMDB
beta-(3-Indolyl)propanoic acidHMDB
beta-Indole-3-propanoic acidHMDB
beta-Indolepropanoic acidHMDB
Β-(3-indolyl)propanoic acidHMDB
Β-indole-3-propanoic acidHMDB
Β-indole-3-propionic acidHMDB
Β-indolepropanoic acidHMDB
Β-indolepropionic acidHMDB
Indole-3-propionic acidChEBI
Chemical FormulaC11H11NO2
Average Mass189.2105 Da
Monoisotopic Mass189.07898 Da
IUPAC Name3-(1H-indol-3-yl)propanoic acid
Traditional Nameindolylpropionic acid
CAS Registry Number830-96-6
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cervus canadensisFooDB
Cucurbita pepoKNApSAcK Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
Ovis ariesFooDB
Phasianus colchicusFooDB
Pisum sativumKNApSAcK Database
Scheffersomyces spartinaeLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
  • 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point134 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.75Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
Water Solubility0.73 g/LALOGPS
pKa (Strongest Acidic)4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.05 m³·mol⁻¹ChemAxon
Polarizability20 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB02758
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000941
KNApSAcK IDC00000115
Chemspider ID3613
KEGG Compound IDNot Available
BiGG IDNot Available
Wikipedia Link3-Indolepropionic acid
PubChem Compound3744
PDB IDNot Available
ChEBI ID43580
Good Scents IDNot Available
General References
  1. 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 ]
  2. 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 ]
  3. Reiter RJ, Guerrero JM, Garcia JJ, Acuna-Castroviejo D: Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin. Ann N Y Acad Sci. 1998 Nov 20;854:410-24. [PubMed:9928448 ]
  4. Kim WS, Gardan L, Rhim SL, Geider K: Erwinia pyrifoliae sp. nov., a novel pathogen that affects Asian pear trees (Pyrus pyrifolia Nakai) Int J Syst Bacteriol. 1999 Apr;49 Pt 2:899-905. doi: 10.1099/00207713-49-2-899. [PubMed:10319516 ]
  5. 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 ]
  6. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Gaetani L, Boscaro F, Pieraccini G, Calabresi P, Romani L, Di Filippo M, Zelante T: Host and Microbial Tryptophan Metabolic Profiling in Multiple Sclerosis. Front Immunol. 2020 Feb 18;11:157. doi: 10.3389/fimmu.2020.00157. eCollection 2020. [PubMed:32132996 ]
  11. Hardeland R, Zsizsik BK, Poeggeler B, Fuhrberg B, Holst S, Coto-Montes A: Indole-3-pyruvic and -propionic acids, kynurenic acid, and related metabolites as luminophores and free-radical scavengers. Adv Exp Med Biol. 1999;467:389-95. doi: 10.1007/978-1-4615-4709-9_49. [PubMed:10721080 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. Dvorak Z, Kopp F, Costello CM, Kemp JS, Li H, Vrzalova A, Stepankova M, Bartonkova I, Jiskrova E, Poulikova K, Vyhlidalova B, Nordstroem LU, Karunaratne CV, Ranhotra HS, Mun KS, Naren AP, Murray IA, Perdew GH, Brtko J, Toporova L, Schon A, Wallace BD, Walton WG, Redinbo MR, Sun K, Beck A, Kortagere S, Neary MC, Chandran A, Vishveshwara S, Cavalluzzi MM, Lentini G, Cui JY, Gu H, March JC, Chatterjee S, Matson A, Wright D, Flannigan KL, Hirota SA, Sartor RB, Mani S: Targeting the pregnane X receptor using microbial metabolite mimicry. EMBO Mol Med. 2020 Apr 7;12(4):e11621. doi: 10.15252/emmm.201911621. Epub 2020 Mar 10. [PubMed:32153125 ]
  16. 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 ]