CHEBI:16411 - indole-3-acetic acid

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ChEBI Name indole-3-acetic acid
ChEBI ID CHEBI:16411
Definition A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24802, CHEBI:5905
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Formula C10H9NO2
Net Charge 0
Average Mass 175.18400
Monoisotopic Mass 175.063
InChI InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
InChIKey SEOVTRFCIGRIMH-UHFFFAOYSA-N
SMILES OC(=O)Cc1c[nH]c2ccccc12
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant hormone
A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
auxin
Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").
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ChEBI Ontology
Outgoing indole-3-acetic acid (CHEBI:16411) has role auxin (CHEBI:22676)
indole-3-acetic acid (CHEBI:16411) has role human metabolite (CHEBI:77746)
indole-3-acetic acid (CHEBI:16411) has role mouse metabolite (CHEBI:75771)
indole-3-acetic acid (CHEBI:16411) has role plant hormone (CHEBI:37848)
indole-3-acetic acid (CHEBI:16411) has role plant metabolite (CHEBI:76924)
indole-3-acetic acid (CHEBI:16411) is a indole-3-acetic acids (CHEBI:24803)
indole-3-acetic acid (CHEBI:16411) is a monocarboxylic acid (CHEBI:25384)
indole-3-acetic acid (CHEBI:16411) is conjugate acid of indole-3-acetate (CHEBI:30854)
Incoming N-(indol-3-ylacetyl)glutamine (CHEBI:70811) has functional parent indole-3-acetic acid (CHEBI:16411)
N-(indole-3-acetyl)-L-aspartic acid (CHEBI:21484) has functional parent indole-3-acetic acid (CHEBI:16411)
N-(indole-3-acetyl)glutamic acid (CHEBI:136547) has functional parent indole-3-acetic acid (CHEBI:16411)
N-(indole-3-acetyl)leucine (CHEBI:133521) has functional parent indole-3-acetic acid (CHEBI:16411)
N-(indole-3-acetyl)phenylalanine (CHEBI:133527) has functional parent indole-3-acetic acid (CHEBI:16411)
N-(indole-3-acetyl)valine (CHEBI:133561) has functional parent indole-3-acetic acid (CHEBI:16411)
indol-3-ylacetyl-CoA (CHEBI:12755) has functional parent indole-3-acetic acid (CHEBI:16411)
indoleacetic acid conjugate (CHEBI:64631) has functional parent indole-3-acetic acid (CHEBI:16411)
methyl (indol-3-yl)acetate (CHEBI:72782) has functional parent indole-3-acetic acid (CHEBI:16411)
indole-3-acetate (CHEBI:30854) is conjugate base of indole-3-acetic acid (CHEBI:16411)
IUPAC Name
1H-indol-3-ylacetic acid
Synonyms Sources
(Indol-3-yl)acetate KEGG COMPOUND
(indol-3-yl)acetic acid UniProt
2-(indol-3-yl)ethanoic acid ChEBI
3-Indolylessigsäure ChEBI
heteroauxin NIST Chemistry WebBook
IAA KEGG COMPOUND
IAA NIST Chemistry WebBook
IES ChEBI
Indole-3-acetic acid KEGG COMPOUND
Indoleacetic acid KEGG COMPOUND
Database Links Databases
C00000100 KNApSAcK
C00954 KEGG COMPOUND
DB07950 DrugBank
HMDB0000197 HMDB
IAC PDBeChem
Indole-3-acetic_acid Wikipedia
View more database links
Registry Numbers Types Sources
143197 Gmelin Registry Number Gmelin
143358 Reaxys Registry Number Reaxys
143358 Beilstein Registry Number Beilstein
87-51-4 CAS Registry Number KEGG COMPOUND
87-51-4 CAS Registry Number ChemIDplus
87-51-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
13610897 PubMed citation Europe PMC
23545355 PubMed citation Europe PMC
24285754 PubMed citation Europe PMC
Last Modified
15 March 2017