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Definition	A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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	ZINC000008551316

Download	Molfile XML SDF

more structures >>

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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

-1.8964 1.1184 0.2425 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.9080 1.5213 1.0589 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5134 -0.0019 -0.3875 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2288 -0.3370 0.0517 C 0 0 0 0 0 0 0 0 0 0 0 0

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

-2.1835 -0.7936 -1.3381 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4165 -1.4924 -0.4315 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2567 -2.3074 -1.3642 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5472 -1.9586 -1.8162 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9481 2.5002 -0.0798 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6406 -0.1513 2.2240 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5093 1.5939 2.3241 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7493 1.5674 0.1280 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9553 2.3509 1.6542 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1119 -0.5306 -1.6742 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3547 -1.7429 -0.1138 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1960 -3.1561 -1.7144 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0232 -2.5562 -2.4955 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 2 0 0 0 0

3 1 1 0 0 0 0

4 1 1 0 0 0 0

9 4 1 0 0 0 0

6 5 4 0 0 0 0

7 5 4 0 0 0 0

9 6 4 0 0 0 0

8 7 4 0 0 0 0

10 7 4 0 0 0 0

9 8 4 0 0 0 0

11 8 4 0 0 0 0

13 10 4 0 0 0 0

12 11 4 0 0 0 0

13 12 4 0 0 0 0

3 14 1 0 0 0 0

4 15 1 0 0 0 0

4 16 1 0 0 0 0

5 17 1 0 0 0 0

6 18 1 0 0 0 0

10 19 1 0 0 0 0

11 20 1 0 0 0 0

12 21 1 0 0 0 0

13 22 1 0 0 0 0

M END): 16 ms

reading 22 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

22 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
[object Object]
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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	Types	Sources
13610897	PubMed citation	Europe PMC
23545355	PubMed citation	Europe PMC
24285754	PubMed citation	Europe PMC

Last Modified

13 December 2024

CHEBI:16411 - indole-3-acetic acid

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