MiMeDB: Showing metabocard for 3-Indolebutyric acid (MMDBc0048024)

Microbial

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:58 UTC

Update Date

2025-09-17 19:36:30 UTC

Metabolite ID

MMDBc0048024

Metabolite Identification

Common Name

3-Indolebutyric acid

Description

3-Indolebutyric acid is an indolic tryptophan metabolite occasionally found in human urine. (PMID:7130309 ). 3-Indolebutyric acid is a plasma and urinary tryptophan-related metabolite related to metabolic and skin diseases. (PMID:15206797 ). Plasma levels of tryptophan metabolites in the umbilical vein and artery are significantly higher than those in the maternal vein. (PMID:1506727 ). 3-Indolebutyric acid has been shown to accelerated glucose uptake in the rat diaphragm. (PMID:6025019 ). 3-Indolebutyric acid is also a microbial netabolite, urinary indole-3-butyrate is produced by Clostridia sp. (PMID:6630445 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1H-Indole-3-butanoic acid	ChEBI
3-Indolyl-gamma-butyric acid	ChEBI
4-(indol-3-yl)Butyric acid	ChEBI
4-indol-3-Ylbutyric acid	ChEBI
IBA	ChEBI
Indole-3-butanoic acid	ChEBI
Indolebutyric acid	ChEBI
Seradix	ChEBI
Indole-3-butyric acid	Kegg
1H-Indole-3-butanoate	Generator
3-Indolyl-g-butyrate	Generator
3-Indolyl-g-butyric acid	Generator
3-Indolyl-gamma-butyrate	Generator
3-Indolyl-γ-butyrate	Generator
3-Indolyl-γ-butyric acid	Generator
4-(indol-3-yl)Butyrate	Generator
4-indol-3-Ylbutyrate	Generator
Indole-3-butanoate	Generator
Indolebutyrate	Generator
Indole-3-butyrate	Generator
3-Indolebutyrate	Generator
Indolebutyric acid, monoammonium salt	MeSH
Indolebutyric acid, monopotassium salt	MeSH
Indolebutyric acid, monosodium salt	MeSH
1H-Indole-3-butyrate	HMDB
1H-Indole-3-butyric acid	HMDB
3-Indole butyrate	HMDB
3-Indole butyric acid	HMDB
3-Indolylbutyric acid	HMDB
3-Iodolebutyrate	HMDB
4-(1H-indol-3-yl)-Butyrate	HMDB
4-(1H-indol-3-yl)-Butyric acid	HMDB
4-(1H-indol-3-yl)Butanoate	HMDB
4-(1H-Indol-3-yl)butanoic acid	HMDB
4-(3-1H-Indolyl)butyrate	HMDB
4-(3-1H-Indolyl)butyric acid	HMDB
4-(3-Indole)-butyrate	HMDB
4-(3-Indole)-butyric acid	HMDB
4-(3-Indolyl)butyrate	HMDB
4-(3-Indolyl)butyric acid	HMDB
4-(Indolyl)- butyrate	HMDB
4-(Indolyl)- butyric acid	HMDB
4-indol-3-Ylbutyric-acid	HMDB
b-Indolebutyrate	HMDB
b-Indolebutyric acid	HMDB
beta-Indolebutyrate	HMDB
beta-Indolebutyric acid	HMDB
Indole 3-butyrate	HMDB
Indole 3-butyric acid	HMDB
Indole-3 butyrate	HMDB
Indole-3 butyric acid	HMDB
Indole-3-butrylate	HMDB
Indole-3-butrylic acid	HMDB
Indolyl-3-butyrate	HMDB
Indolyl-3-butyric acid	HMDB
3-Indolebutyric acid	ChEBI
4-(1H-Indol-3-yl)butyric acid	HMDB
4-(3-Indolyl)butanoic acid	HMDB
4-(Indol-3-yl)butanoate	HMDB
[3-(3-Indolyl)propyl]carboxylic acid	HMDB
beta-IBA	HMDB
beta-Indolylbutyric acid	HMDB
gamma-(Indol-3-yl)butyric acid	HMDB
gamma-(Indole-3)-butyric acid	HMDB
β-IBA	HMDB
β-Indolebutyric acid	HMDB
β-Indolylbutyric acid	HMDB
γ-(Indol-3-yl)butyric acid	HMDB
γ-(Indole-3)-butyric acid	HMDB

Molecular Formula

C₁₂H₁₃NO₂

Average Mass

203.2371

Monoisotopic Mass

203.094628665

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

InChI Key

JTEDVYBZBROSJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid (CHEBI:33070 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Neuron
Platelet

Tissue Locations

Neuron
Platelet

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

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Schizophrenia		Association		Pubchem	115032; 7126379; 2480613; 17276036; 11877547; 12796220; 7595563; 20814316; 25004141; 24713860; 23823132; 2415198; 1694425; 7711000; 19390223; 22024767; 22007635; 21483431; 3741918; 11979513; 20206656; 436860; 19401681; 6184954; 26952797; 22800120; 24789758; 22944140; 22892715; 17440431; 25729574; 22257447

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	22800120

External Links

HMDB ID

HMDB0002096

DrugBank ID

DB02740

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Indole-3-butyric_acid

METLIN ID

6485

PubChem Compound

8617

PDB ID

Not Available

ChEBI ID

33070

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Eguchi K, Kamimura S, Yonezawa M, Mitsui Y, Mizutani Y, Kudo T: [Tryptophan and its metabolite concentrations in human plasma during the perinatal period]. Nihon Sanka Fujinka Gakkai Zasshi. 1992 Jun;44(6):663-8. [PubMed:1506727 ]
Silverstein MN, Wakim KG, Bahn RC: The influence of tryptophan metabolites on tissue uptake of glucose. Metabolism. 1967 May;16(5):410-2. doi: 10.1016/0026-0495(67)90131-x. [PubMed:6025019 ]
Lombard GL, Dowell VR Jr: Comparison of three reagents for detecting indole production by anaerobic bacteria in microtest systems. J Clin Microbiol. 1983 Sep;18(3):609-13. doi: 10.1128/jcm.18.3.609-613.1983. [PubMed:6630445 ]
Tonelli D, Gattavecchia E, Gandolfi M: Thin-layer chromatographic determination of indolic tryptophan metabolites in human urine using Sep-Pak C18 extraction. J Chromatogr. 1982 Sep 10;231(2):283-9. doi: 10.1016/s0378-4347(00)81853-8. [PubMed:7130309 ]
Meininger V, Chaineau E, Soudiere B: [Effect of naftidrofuryl (LS129) on axonal growth]. Rev Neurol (Paris). 1994;150(2):115-22. [PubMed:7863151 ]
Merle M, Gilbert A, Fredenucci JF, Petry D, Foliguet B, Mosnier M: Experimental and clinical study of the effect of naftidrofuryl on the recovery from peripheral nerve lesions. Microsurgery. 1994;15(3):179-86. doi: 10.1002/micr.1920150308. [PubMed:8015423 ]
Hirsch JL, Bensoussan JJ, Mosnier M, Lehert P: [Evaluation of the efficacy and tolerance of naftidrofuryl in patients presenting with exertional angina. Multicenter double-blind versus placebo study]. Ann Cardiol Angeiol (Paris). 1999 Feb;48(2):137-45. [PubMed:12555338 ]
Marklova E, Albahri Z, Nozickova M: HPLC profiling of Trp-related metabolites in humans. Adv Exp Med Biol. 2003;527:739-44. doi: 10.1007/978-1-4615-0135-0_87. [PubMed:15206797 ]

Showing metabocard for 3-Indolebutyric acid (MMDBc0048024)

MOL for #<Metabolite:0x00007ff8157360a8>

3D MOL for #<Metabolite:0x00007ff8157360a8>

3D SDF for #<Metabolite:0x00007ff8157360a8>

3D-SDF for #<Metabolite:0x00007ff8157360a8>

PDB for #<Metabolite:0x00007ff8157360a8>

3D PDB for #<Metabolite:0x00007ff8157360a8>

SMILES for #<Metabolite:0x00007ff8157360a8>

INCHI for #<Metabolite:0x00007ff8157360a8>

Structure for #<Metabolite:0x00007ff8157360a8>

3D Structure for #<Metabolite:0x00007ff8157360a8>