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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2020-03-26 17:03:03 UTC
HMDB IDHMDB0002302
Secondary Accession Numbers
  • HMDB02302
Metabolite 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. Indole-3-propionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress (PMID: 10319516 ). 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
Data?1585066421
Synonyms
ValueSource
beta-(3-Indolyl)propionic acidChEBI
Indolepropionic acidChEBI
b-(3-Indolyl)propionateGenerator
b-(3-Indolyl)propionic acidGenerator
beta-(3-Indolyl)propionateGenerator
Β-(3-indolyl)propionateGenerator
Β-(3-indolyl)propionic acidGenerator
IndolepropionateGenerator
Indole-3-propionateGenerator
3-IndolepropionateHMDB
1H-Indole-3-propionateHMDB
1H-Indole-3-propionic acidHMDB
3-(1H-indol-3-yl)PropanoateHMDB
3-(1H-indol-3-yl)Propanoic acidHMDB
3-(1H-indol-3-yl)PropionateHMDB
3-(1H-indol-3-yl)Propionic acidHMDB
3-(2-Carboxyethyl)-1H-indoleHMDB
3-(3-Indolyl)propanoateHMDB
3-(3-Indolyl)propanoic acidHMDB
3-(3-Indolyl)propionateHMDB
3-(3-Indolyl)propionic acidHMDB
b-Indole-3-propionateHMDB
b-Indole-3-propionic acidHMDB
b-IndolepropionateHMDB
b-Indolepropionic acidHMDB
beta-Indole-3-propionateHMDB
beta-Indole-3-propionic acidHMDB
beta-IndolepropionateHMDB
beta-Indolepropionic acidHMDB
IPAHMDB
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 Molecular Weight189.2105
Monoisotopic Molecular Weight189.078978601
IUPAC Name3-(1H-indol-3-yl)propanoic acid
Traditional Nameindolylpropionic acid
CAS Registry Number830-96-6
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 KeyGOLXRNDWAUTYKT-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.75HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP2.04ALOGPS
logP2.15ChemAxon
logS-2.4ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-1900000000-7964cf38946a23d63104Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-1900000000-7964cf38946a23d63104Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-1900000000-79b70b4d80349fed40a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-8910000000-cc3bf52f2cbb339eea4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-5bf41cc0642ca12d91ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2bdd32c86cd63a03b739Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-8900000000-fa98f64c6c35db6c3425Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-1900000000-7964cf38946a23d63104Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00e9-0900000000-aa04863f4b124d617168Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-c3c14c76cdb38c3798f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-4be398aaf9b927637228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5f65be50e34cc07d1a77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-2900000000-747697a81c30bbf35e01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-76970d017d781fd87474Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-35d9289d5e0f2905c29dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-8a8af8b32271e2d2eef0Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-de72f9061ea0bb241ef7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.481 (0.291 - 1.095) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothHemodialysis patients with colon details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB02758
Phenol Explorer Compound IDNot Available
FooDB IDFDB000941
KNApSAcK IDC00000115
Chemspider ID3613
KEGG Compound IDNot Available
BioCyc IDINDOLE-PROPIONATE
BiGG IDNot Available
Wikipedia Link3-Indolepropionic acid
METLIN ID6602
PubChem Compound3744
PDB IDNot Available
ChEBI ID43580
Food Biomarker OntologyNot Available
VMH IDIND3PPA
References
Synthesis ReferenceJohnson, Herbert E.; Crosby, Donald G. 3-Indolepropionic acid. Journal of Organic Chemistry (1960), 25 569-71.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  8. Zhao ZH, Xin FZ, Xue Y, Hu Z, Han Y, Ma F, Zhou D, Liu XL, Cui A, Liu Z, Liu Y, Gao J, Pan Q, Li Y, Fan JG: Indole-3-propionic acid inhibits gut dysbiosis and endotoxin leakage to attenuate steatohepatitis in rats. Exp Mol Med. 2019 Sep 10;51(9):1-14. doi: 10.1038/s12276-019-0304-5. [PubMed:31506421 ]
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  31. 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 ]
  32. 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 Mar 10:e11621. doi: 10.15252/emmm.201911621. [PubMed:32153125 ]