Structure via PubChem · Public domain (PubChem)
indole-3-carboxaldehyde
Sign in to saveAlso known as 1H-Indole-3-carboxaldehyde, 1H-indole-3-carbaldehyde, I3CHO, indole-3-carbaldehyde, Indole-3-aldehyde, 3-Formylindole, beta-Indolylaldehyde, 3-Indolecarbaldehyde
Indole-3-carbaldehyde (I3A), also known as indole-3-aldehyde and 3-formylindole, is a metabolite of dietary which is synthesized by human gastrointestinal bacteria, particularly species of the Lactobacillus genus. I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells, in turn stimulating the production of interleukin-22 which facilitates mucosal reactivity.
Chemical data
- Formula
- C9H7NO
- Molecular weight
- 145.16 g/mol
- IUPAC name
- 1H-indole-3-carbaldehyde
- SMILES
- C1=CC=C2C(=C1)C(=CN2)C=O
- InChIKey
- OLNJUISKUQQNIM-UHFFFAOYSA-N
- XLogP
- 1.7
- Polar surface area
- 32.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- indole alkaloid
- Mass
- 145.053
Show 4 more facts
- canonical SMILES
- C1=CC=C2C(=C1)C(=CN2)C=O
- chemical formula
- C₉H₇NO
- melting point
- 197.0
- Commons category
- Indole-3-carbaldehyde
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Biosynthesis in humans and cellular effects
- Chemistry
- Antifungal properties
- References
Indole-3-carbaldehyde (I3A), also known as indole-3-aldehyde and 3-formylindole, is a metabolite of dietary which is synthesized by human gastrointestinal bacteria, particularly species of the Lactobacillus genus. I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells, in turn stimulating the production of interleukin-22 which facilitates mucosal reactivity.
==Biosynthesis in humans and cellular effects==
Excerpted from Wikipedia’s “indole-3-carboxaldehyde” article, available under the CC BY-SA 4.0 licence.