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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:47 UTC

Update Date

2023-02-21 17:16:19 UTC

HMDB ID

HMDB0002302

Secondary Accession Numbers

HMDB02302

Metabolite 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>
HMDB0002302

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

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

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002302)
Saliva (HMDB: HMDB0002302)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0002302)
Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002302)

Source

Endogenous

Endogenous (HMDB: HMDB0002302)

Plant

Fabaceae (HMDB: HMDB0002302)

Microbe

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

Exogenous

Food

Food (HMDB: HMDB0002302)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002302)

Physical Properties

State

Solid

Experimental Molecular 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,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.926	31661259
DarkChem	[M-H]-	140.402	31661259
DeepCCS	[M+H]+	137.686	30932474
DeepCCS	[M-H]-	134.971	30932474
DeepCCS	[M-2H]-	171.224	30932474
DeepCCS	[M+Na]+	146.762	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.3	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.7	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-propionic acid	OC(=O)CCC1=CNC2=C1C=CC=C2	3392.1	Standard polar	33892256
Indole-3-propionic acid	OC(=O)CCC1=CNC2=C1C=CC=C2	1776.1	Standard non polar	33892256
Indole-3-propionic acid	OC(=O)CCC1=CNC2=C1C=CC=C2	1984.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-propionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=C[NH]C2=CC=CC=C12	2028.0	Semi standard non polar	33892256
Indole-3-propionic acid,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCC(=O)O)C2=CC=CC=C21	2074.8	Semi standard non polar	33892256
Indole-3-propionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2059.2	Semi standard non polar	33892256
Indole-3-propionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2030.8	Standard non polar	33892256
Indole-3-propionic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2245.2	Standard polar	33892256
Indole-3-propionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C2=CC=CC=C12	2288.2	Semi standard non polar	33892256
Indole-3-propionic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCC(=O)O)C2=CC=CC=C21	2334.4	Semi standard non polar	33892256
Indole-3-propionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2522.1	Semi standard non polar	33892256
Indole-3-propionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2470.3	Standard non polar	33892256
Indole-3-propionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2471.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Indole-3-propionic acid EI-B (Non-derivatized)	splash10-001i-1900000000-7964cf38946a23d63104	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Indole-3-propionic acid EI-B (Non-derivatized)	splash10-001i-1900000000-7964cf38946a23d63104	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-propionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-1900000000-79b70b4d80349fed40a2	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-propionic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-8910000000-cc3bf52f2cbb339eea4a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-propionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-1900000000-de72f9061ea0bb241ef7	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0900000000-5bf41cc0642ca12d91dd	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004i-0900000000-2bdd32c86cd63a03b739	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-8900000000-fa98f64c6c35db6c3425	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid EI-B (Unknown) , Positive-QTOF	splash10-001i-1900000000-7964cf38946a23d63104	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid LC-ESI-IT , positive-QTOF	splash10-00e9-0900000000-aa04863f4b124d617168	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid , positive-QTOF	splash10-001i-1900000000-c3c14c76cdb38c3798f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 20V, Positive-QTOF	splash10-001i-1900000000-db653a92384089e7272c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 35V, Positive-QTOF	splash10-001i-0900000000-2837a9689ebb97e17c89	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Negative-QTOF	splash10-03di-9400000000-20084f0045f0393dcaad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Negative-QTOF	splash10-0a4i-9500000000-d39c747b7db2e42acefc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Positive-QTOF	splash10-001i-0900000000-8927c2758d647a804f4a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 20V, Negative-QTOF	splash10-0a4i-9300000000-282c233baa3c0e5bf365	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Positive-QTOF	splash10-001i-4900000000-1e1179cded69a29a5047	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 20V, Negative-QTOF	splash10-0a4i-9300000000-0aaa5de6ae1a4aafa661	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Positive-QTOF	splash10-001i-0900000000-1b79a66b12c3205108c5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 35V, Negative-QTOF	splash10-0aor-6900000000-909aa5100e4655d54267	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Negative-QTOF	splash10-05mo-9600000000-e85aca97bdac26c3d258	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Positive-QTOF	splash10-003r-4900000000-29142c5171637b4d5e5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Negative-QTOF	splash10-0a4i-9600000000-bc2ddd9f185d76d60d50	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Positive-QTOF	splash10-006x-0900000000-4be398aaf9b927637228	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 20V, Positive-QTOF	splash10-0006-0900000000-5f65be50e34cc07d1a77	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Positive-QTOF	splash10-00lu-2900000000-747697a81c30bbf35e01	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 10V, Negative-QTOF	splash10-000i-0900000000-76970d017d781fd87474	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 20V, Negative-QTOF	splash10-000l-1900000000-35d9289d5e0f2905c29d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-propionic acid 40V, Negative-QTOF	splash10-052f-9700000000-8a8af8b32271e2d2eef0	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21784895	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.481 (0.291 - 1.095) uM	Adult (>18 years old)	Not Specified	Normal	14606996	details
Blood	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	21784895	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21190195	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hemodialysis patients with colon	21784895	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral squamous cell carcinoma (OSCC)	21190195	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral leukoplakia (OLK)	21190195	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

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 ]
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 ]
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

114500 (Colorectal cancer)

External Links

DrugBank ID

DB02758

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

IND3PPA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Johnson, 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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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 ]
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 ]
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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. [PubMed:7378938 ]
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 ]
Galligan JJ: Beneficial actions of microbiota-derived tryptophan metabolites. Neurogastroenterol Motil. 2018 Feb;30(2). doi: 10.1111/nmo.13283. [PubMed:29341448 ]
Cason CA, Dolan KT, Sharma G, Tao M, Kulkarni R, Helenowski IB, Doane BM, Avram MJ, McDermott MM, Chang EB, Ozaki CK, Ho KJ: Plasma microbiome-modulated indole- and phenyl-derived metabolites associate with advanced atherosclerosis and postoperative outcomes. J Vasc Surg. 2018 Nov;68(5):1552-1562.e7. doi: 10.1016/j.jvs.2017.09.029. Epub 2017 Dec 13. [PubMed:29248242 ]
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 ]
Rothhammer V, Mascanfroni ID, Bunse L, Takenaka MC, Kenison JE, Mayo L, Chao CC, Patel B, Yan R, Blain M, Alvarez JI, Kebir H, Anandasabapathy N, Izquierdo G, Jung S, Obholzer N, Pochet N, Clish CB, Prinz M, Prat A, Antel J, Quintana FJ: Type I interferons and microbial metabolites of tryptophan modulate astrocyte activity and central nervous system inflammation via the aryl hydrocarbon receptor. Nat Med. 2016 Jun;22(6):586-97. doi: 10.1038/nm.4106. Epub 2016 May 9. [PubMed:27158906 ]
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 ]
Mimori S, Kawada K, Saito R, Takahashi M, Mizoi K, Okuma Y, Hosokawa M, Kanzaki T: Indole-3-propionic acid has chemical chaperone activity and suppresses endoplasmic reticulum stress-induced neuronal cell death. Biochem Biophys Res Commun. 2019 Oct 1;517(4):623-628. doi: 10.1016/j.bbrc.2019.07.074. Epub 2019 Aug 1. [PubMed:31378367 ]
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 ]
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 ]
Alexeev EE, Lanis JM, Kao DJ, Campbell EL, Kelly CJ, Battista KD, Gerich ME, Jenkins BR, Walk ST, Kominsky DJ, Colgan SP: Microbiota-Derived Indole Metabolites Promote Human and Murine Intestinal Homeostasis through Regulation of Interleukin-10 Receptor. Am J Pathol. 2018 May;188(5):1183-1194. doi: 10.1016/j.ajpath.2018.01.011. Epub 2018 Feb 16. [PubMed:29454749 ]
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 ]
Abildgaard A, Elfving B, Hokland M, Wegener G, Lund S: The microbial metabolite indole-3-propionic acid improves glucose metabolism in rats, but does not affect behaviour. Arch Physiol Biochem. 2018 Oct;124(4):306-312. doi: 10.1080/13813455.2017.1398262. Epub 2017 Nov 7. [PubMed:29113509 ]
Jennis M, Cavanaugh CR, Leo GC, Mabus JR, Lenhard J, Hornby PJ: Microbiota-derived tryptophan indoles increase after gastric bypass surgery and reduce intestinal permeability in vitro and in vivo. Neurogastroenterol Motil. 2018 Feb;30(2). doi: 10.1111/nmo.13178. Epub 2017 Aug 7. [PubMed:28782205 ]
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Karbownik M, Stasiak M, Zasada K, Zygmunt A, Lewinski A: Comparison of potential protective effects of melatonin, indole-3-propionic acid, and propylthiouracil against lipid peroxidation caused by potassium bromate in the thyroid gland. J Cell Biochem. 2005 May 1;95(1):131-8. doi: 10.1002/jcb.20404. [PubMed:15723291 ]
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Showing metabocard for Indole-3-propionic acid (HMDB0002302)

MOL for HMDB0002302 (Indole-3-propionic acid)

3D MOL for HMDB0002302 (Indole-3-propionic acid)

3D SDF for HMDB0002302 (Indole-3-propionic acid)

3D-SDF for HMDB0002302 (Indole-3-propionic acid)

PDB for HMDB0002302 (Indole-3-propionic acid)

3D PDB for HMDB0002302 (Indole-3-propionic acid)

SMILES for HMDB0002302 (Indole-3-propionic acid)

INCHI for HMDB0002302 (Indole-3-propionic acid)

Structure for HMDB0002302 (Indole-3-propionic acid)

3D Structure for HMDB0002302 (Indole-3-propionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra