indole-3-acetic acid (CHEBI:16411)

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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Definition	A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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

Supplier Information	We are unable to retrieve the vendor information for this entry at this time. Please try again later.

Download	Molfile XML SDF

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Mrv0541 01221409113D

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Mrv0541 01221409113D

22 23 0 0 0 0 999 V2000

2.5650 0.9384 0.6705 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4800 0.1349 0.5690 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5945 1.9020 -0.0877 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4911 0.7527 1.6268 C 0 0 1 0 0 0 0 0 0 0 0 0

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0.1778 0.6480 0.9533 C 0 0 0 0 0 0 0 0 0 0 0 0

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6 5 4 0 0 0 0

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M END): 26 ms

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Wikipedia	License
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.
Read full article at Wikipedia

Formula

C10H9NO2

Net Charge

Average Mass

175.18400

Monoisotopic Mass

175.06333

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:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	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").

View more via ChEBI Ontology

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	2-phenylethyl 1H-indol-3-ylacetate (CHEBI:141317) has functional parent indole-3-acetic acid (CHEBI:16411) 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) N-[(6-hydroxyindol-3-yl)acetyl]phenylalanine (CHEBI:136939) 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) 3-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-L-alanine (CHEBI:195384) is a 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
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

Manual Xrefs	Databases
1106	BPDB
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
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

Kryuchkova YV, Burygin GL, Gogoleva NE, Gogolev YV, Chernyshova MP, Makarov OE, Fedorov EE, Turkovskaya OV (2014)
Isolation and characterization of a glyphosate-degrading rhizosphere strain, Enterobacter cloacae K7.
Microbiological research 169, 99-105 [PubMed:23545355]
[show Abstract]

Tanaka K, Hayashi K, Natsume M, Kamiya Y, Sakakibara H, Kawaide H, Kasahara H (2014)
UGT74D1 catalyzes the glucosylation of 2-oxindole-3-acetic acid in the auxin metabolic pathway in Arabidopsis.
Plant & cell physiology 55, 218-228 [PubMed:24285754]
[show Abstract]

WEISSBACH H, KING W, SJOERDSMA A, UDENFRIEND S (1959)
Formation of indole-3-acetic acid and tryptamine in animals: a method for estimation of indole-3-acetic acid in tissues.
The Journal of biological chemistry 234, 81-86 [PubMed:13610897]

Last Modified

13 December 2024

CHEBI:16411 - indole-3-acetic acid

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