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CHEBI:232059 - 5-adamantyl-IAA

ChEBI IDCHEBI:232059
ChEBI Name5-adamantyl-IAA
Stars
DefinitionA member of the class of indole-3-acetic acids that is (1H-indol-3-yl)acetic acid substituted by an adamantan-1-yl group at position 5. It is a synthetic auxin that binds to the modified auxin receptor, shows stronger binding affinity than natural auxin, and induces protein degradation.
Last Modified4 October 2024
SubmitterBrianna Xu
DownloadsMolfile
FormulaC20H23NO2
Net Charge0
Average Mass309.409
Monoisotopic Mass309.17288
SMILESO=C(O)Cc1cnc2ccc(C34CC5CC(CC(C5)C3)C4)cc12
InChIInChI=1S/C20H23NO2/c22-19(23)6-15-11-21-18-2-1-16(7-17(15)18)20-8-12-3-13(9-20)5-14(4-12)10-20/h1-2,7,11-14,21H,3-6,8-10H2,(H,22,23)
InChIKeyYVLXUUNCRVEHPG-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
synthetic auxin  A synthetic compound exhibiting auxin activity.
ChEBI Ontology
Outgoing Relation(s)
5-adamantyl-IAA (CHEBI:232059) has role synthetic auxin (CHEBI:26841)
5-adamantyl-IAA (CHEBI:232059) is a adamantanes (CHEBI:51339)
5-adamantyl-IAA (CHEBI:232059) is a indole-3-acetic acids (CHEBI:24803)
5-adamantyl-IAA (CHEBI:232059) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
[5-(adamantan-1-yl)-1H-indol-3-yl]acetic acid
Synonyms  Source
2-[5-(1-adamantyl)-1H-indol-3-yl]acetic acidSUBMITTER
2-(5-(adamantan-1-yl)-1H-indol-3-yl)acetic acidSUBMITTER
2-[5-(adamantan-1-yl)-1H-indol-3-yl]acetic acidChEBI
[5-(tricyclo[3.3.1.13,7]decan-1-yl)-1H-indol-3-yl]acetic acidIUPAC
Registry NumbersSources
CAS:2244426-40-0SUBMITTER
Citations