MiMeDB: Showing metabocard for Indole-3-propionate (MMDBc0049973)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:47:23 UTC

Update Date

2022-12-15 22:52:20 UTC

Metabolite ID

MMDBc0049973

Metabolite Identification

Common Name

Indole-3-propionate

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>
MMDBc0049973

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₁NO₂

Average Mass

189.2105

Monoisotopic Mass

189.078978601

IUPAC Name

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

Traditional Name

indolylpropionic acid

CAS Registry Number

Not Available

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

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-1900000000-7964cf38946a23d63104	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-1900000000-7964cf38946a23d63104	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-1900000000-79b70b4d80349fed40a2	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-8910000000-cc3bf52f2cbb339eea4a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-5bf41cc0642ca12d91dd	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-2bdd32c86cd63a03b739	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-8900000000-fa98f64c6c35db6c3425	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001i-1900000000-7964cf38946a23d63104	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-00e9-0900000000-aa04863f4b124d617168	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-1900000000-c3c14c76cdb38c3798f0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-db653a92384089e7272c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-2837a9689ebb97e17c89	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9400000000-20084f0045f0393dcaad	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9500000000-d39c747b7db2e42acefc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-8927c2758d647a804f4a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-282c233baa3c0e5bf365	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-4900000000-1e1179cded69a29a5047	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-0aaa5de6ae1a4aafa661	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-1b79a66b12c3205108c5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0aor-6900000000-909aa5100e4655d54267	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9600000000-e85aca97bdac26c3d258	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-003r-4900000000-29142c5171637b4d5e5f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9600000000-bc2ddd9f185d76d60d50	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0900000000-4be398aaf9b927637228	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-5f65be50e34cc07d1a77	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lu-2900000000-747697a81c30bbf35e01	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-76970d017d781fd87474	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-1900000000-35d9289d5e0f2905c29d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9700000000-8a8af8b32271e2d2eef0	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-1900000000-de72f9061ea0bb241ef7	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2021-10-10	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012726	3-(indol-3-yl)pyruvic acid	Indole-3-propionate	Not Available		Manually annotated by MiMeDB team	Manually annotated by MiMeDB team
MMDBr0012728	Indolelactic acid	Indole-3-propionate	Not Available		Manually annotated by MiMeDB team	Manually annotated by MiMeDB team
MMDBr0008223	Hydrogen Ion	Indole-3-propionate	Not Available	Tryptophan deamination, forming indole-3-propionate (hypothetical reaction)	VMH	30371894
MMDBr0010947	Hydrogen Ion	Hydrogen Ion	Not Available	Indole-3-propionate transport via proton symport reversible	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Atherosclerosis	decreased	Association	Human plasma	PubMed	29248242
Huntington's disease	decreased	Association	Human plasma	PubMed	26273688
Vasopressor		Animal_model	aorta tissue culture	PubMed	31211619
Aryl hydrocarbon receptor	agonist	Cell culture	House mouse AZ-AHR cells (HepG2)	PubMed	32283770

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	6	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.481		0.291	1.095	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	14606996

External Links

HMDB ID

HMDB0002302

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1111/j.1749-6632.1998.tb09920.x. [PubMed:9928448 ]
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 ]
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. doi: 10.1074/jbc.274.31.21937. [PubMed:10419516 ]
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 ]
Karbownik M, Reiter RJ, Garcia JJ, Cabrera J, Burkhardt S, Osuna C, Lewinski A: Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction. J Cell Biochem. 2001;81(3):507-13. [PubMed:11255233 ]
Karbownik M, Garcia JJ, Lewinski A, Reiter RJ: Carcinogen-induced, free radical-mediated reduction in microsomal membrane fluidity: reversal by indole-3-propionic acid. J Bioenerg Biomembr. 2001 Feb;33(1):73-8. doi: 10.1023/a:1005628808688. [PubMed:11460928 ]
Bendheim PE, Poeggeler B, Neria E, Ziv V, Pappolla MA, Chain DG: Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease. J Mol Neurosci. 2002 Aug-Oct;19(1-2):213-7. doi: 10.1007/s12031-002-0036-0. [PubMed:12212784 ]
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Showing metabocard for Indole-3-propionate (MMDBc0049973)

MOL for #<Metabolite:0x00007fe2d43aa660>

3D MOL for #<Metabolite:0x00007fe2d43aa660>

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3D-SDF for #<Metabolite:0x00007fe2d43aa660>

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3D PDB for #<Metabolite:0x00007fe2d43aa660>

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Structure for #<Metabolite:0x00007fe2d43aa660>

3D Structure for #<Metabolite:0x00007fe2d43aa660>