MiMeDB: Showing metabocard for Indoleacrylic acid (MMDBc0047978)

Co-metabolite

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-12-11 00:18:39 UTC

Update Date

2025-09-17 19:36:28 UTC

Metabolite ID

MMDBc0047978

Metabolite Identification

Common Name

Indoleacrylic acid

Description

Indoleacrylic acid, also known as 3-indoleacrylate or IA, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleacrylic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make indoleacrylic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Indoleacrylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(3-Indolyl)acrylic acid	ChEBI
3-Indoleacrylic acid	ChEBI
3-Indolylacrylic acid	ChEBI
Indole-3-acrylic acid	ChEBI
Indole-3beta-acrylic acid	ChEBI
trans-3-Indoleacrylic acid	ChEBI
trans-beta-Indoleacrylic acid	ChEBI
3-(3-Indolyl)acrylate	Generator
3-Indoleacrylate	Generator
3-Indolylacrylate	Generator
Indole-3-acrylate	Generator
Indole-3b-acrylate	Generator
Indole-3b-acrylic acid	Generator
Indole-3beta-acrylate	Generator
Indole-3β-acrylate	Generator
Indole-3β-acrylic acid	Generator
trans-3-Indoleacrylate	Generator
trans-b-Indoleacrylate	Generator
trans-b-Indoleacrylic acid	Generator
trans-beta-Indoleacrylate	Generator
trans-Β-indoleacrylate	Generator
trans-Β-indoleacrylic acid	Generator
Indoleacrylate	Generator
(e)-3-(indol-3-yl)Acrylate	HMDB
Indoleacrylic acid, (e)-isomer	HMDB
Indoleacrylic acid, sodium salt	HMDB
Indole acrylic acid	HMDB
(2E)-3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
(e)-3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
(e)-3-(1H-indol-3-yl)Prop-2-enoic acid	HMDB
(e)-Indole-3-acrylic acid	HMDB
3-(1H-indol-3-yl)-2-Propenoic acid	HMDB
3-(1H-indol-3-yl)Acrylic acid	HMDB
3-(indol-3-yl)Prop-2-enoic acid	HMDB
3-beta-Indoleacrylic acid	HMDB
3-Β-indoleacrylic acid	HMDB
IA	HMDB
IAcrA	HMDB
Indoleacrylic acid	ChEBI

Molecular Formula

C₁₁H₉NO₂

Average Mass

187.198

Monoisotopic Mass

187.063328534

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+

InChI Key

PLVPPLCLBIEYEA-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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
Feces
Urine

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012710	L-Tryptophan	Indoleacrylic acid	tryptophan ammonia lyase	ammonia-lyase	RHEA; KEGG	25961404
MMDBr0012709	Indoleacrylic acid	3-Indoleacryloyl-CoA	acyl CoA synthetase	conjugation; phase-II biotransformation; glycine-conjugation	HMDB	?
MMDBr0012708	3-Indoleacryloyl-CoA	Indolylacryloylglycine	glycine acyltransferase	conjugation; phase-II biotransformation; glycine-conjugation	HMDB KEGG	7802672; 22071172

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Duchenne muscular dystrophy				HMDB	10707769
Anti-inflammatory		Cell culture	Human Peripheral blood mononuclear cells	PubMed	28704649
Intestinal epithelial barrier	promotes function	Animal_model	goblet cells	PubMed	28704649
Oxidative stress	reduces	Cell culture	Peripheral blood mononuclear cells	PubMed	28704649
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

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 Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000734

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112378

KNApSAcK ID

Not Available

Chemspider ID

4524636

KEGG Compound ID

Not Available

BioCyc ID

CPD-11578

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5375048

PDB ID

Not Available

ChEBI ID

132244

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. doi: 10.1007/BF01361665. [PubMed:10707769 ]
Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007. [PubMed:28704649 ]
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 ]

Showing metabocard for Indoleacrylic acid (MMDBc0047978)

MOL for #<Metabolite:0x00007fe119a8a168>

3D MOL for #<Metabolite:0x00007fe119a8a168>

3D SDF for #<Metabolite:0x00007fe119a8a168>

3D-SDF for #<Metabolite:0x00007fe119a8a168>

PDB for #<Metabolite:0x00007fe119a8a168>

3D PDB for #<Metabolite:0x00007fe119a8a168>

SMILES for #<Metabolite:0x00007fe119a8a168>

INCHI for #<Metabolite:0x00007fe119a8a168>

Structure for #<Metabolite:0x00007fe119a8a168>

3D Structure for #<Metabolite:0x00007fe119a8a168>