CHEBI:31174 - adapalene

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ChEBI Name adapalene
ChEBI ID CHEBI:31174
Definition A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H28O3
Net Charge 0
Average Mass 412.521
Monoisotopic Mass 412.204
InChI InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
InChIKey LZCDAPDGXCYOEH-UHFFFAOYSA-N
SMILES C1C2(CC3CC(CC1C3)C2)C4=C(C=CC(=C4)C5=CC=C6C(=C5)C=CC(=C6)C(=O)O)OC
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): EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of cyclin-dependent kinase (EC 2.7.11.22).
Application(s): dermatologic drug
A drug used to treat or prevent skin disorders or for the routine care of skin.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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ChEBI Ontology
Outgoing adapalene (CHEBI:31174) has functional parent CD437 (CHEBI:88334)
adapalene (CHEBI:31174) has role dermatologic drug (CHEBI:50177)
adapalene (CHEBI:31174) has role EC 2.7.11.22 (cyclin-dependent kinase) inhibitor (CHEBI:82665)
adapalene (CHEBI:31174) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
adapalene (CHEBI:31174) is a adamantanes (CHEBI:51339)
adapalene (CHEBI:31174) is a monocarboxylic acid (CHEBI:25384)
adapalene (CHEBI:31174) is a naphthoic acid (CHEBI:25483)
IUPAC Name
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid
INNs Sources
adapalène ChEBI
adapalene ChemIDplus
adapaleno ChemIDplus
adapalenum ChemIDplus
Synonym Source
6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid ChemIDplus
Brand Names Sources
Adaferin DrugBank
Differine DrugBank
Database Links Databases
87 DrugCentral
Adapalene Wikipedia
D01112 KEGG DRUG
DB00210 DrugBank
EP199636 Patent
LSM-37048 LINCS
US4717720 Patent
View more database links
Registry Number Type Source
106685-40-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11594670 PubMed citation Europe PMC
12833014 PubMed citation Europe PMC
25016424 PubMed citation Europe PMC
26398439 PubMed citation Europe PMC
26483036 PubMed citation Europe PMC
Last Modified
22 February 2017