Structure via PubChem · Public domain (PubChem)
indoleacetic acid
Sign in to saveAlso known as Indolylacetic acid, IAA, heteroauxin, 2-(indol-3-yl)ethanoic acid, (Indol-3-yl)acetate, 2-(1H-indol-3-yl)ethanoic acid, 2-(1H-indol-3-yl)acetic acid, beta-Indoleacetate
chemical compound
Chemical data
- Formula
- C10H9NO2
- Molecular weight
- 175.18 g/mol
- IUPAC name
- 2-(1H-indol-3-yl)acetic acid
- SMILES
- C1=CC=C2C(=C1)C(=CN2)CC(=O)O
- InChIKey
- SEOVTRFCIGRIMH-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 53.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
5,365 papers- Phocaeicola vulgatus induces immunotherapy resistance in hepatocellular carcinoma via reducing indoleacetic acid production.Cell reports. Medicine · 2025
- Gut microbiota-derived 3-indoleacetic acid confers a protection against sepsis-associated encephalopathy through microglial aryl hydrocarbon receptors.Experimental neurology · 2025
- Inoculating indoleacetic acid bacteria promotes the enrichment of halotolerant bacteria during secondary fermentation of composting.Journal of environmental management · 2022
- Synthesis and bioactivity of indoleacetic acid-carbendazim and its effects on Cylindrocladium parasiticum.Pesticide biochemistry and physiology · 2019
- 3-Indoleacetic Acid-Modified Chondroitin Sulfate-Mediated Paclitaxel Nanocrystal Assembly for the Treatment of Pancreatic Cancer.ACS applied materials & interfaces · 2025
via PubMed
Wikidata facts
- Subclass of
- indole alkaloid
- Has part
- carbon
- Mass
- 175.063
Show 5 more facts
- Commons category
- Indole acetic acid
- canonical SMILES
- C1=CC=C2C(=C1)C(=CN2)CC(=O)O
- chemical formula
- C₁₀H₉NO₂
- found in taxon
- Diospyros kaki
- subject has role
- primary metabolite
via Wikidata · CC0
~8 min read
Encyclopedic overview
Indole-3-acetic acid (IAA, 3-IAA) is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.
Biosynthesis
Excerpted from Wikipedia’s “indoleacetic acid” article, available under the CC BY-SA 4.0 licence.