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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at The data is made available under the Creative Commons License (CC BY 3.0, For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

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Accession:CHEBI:88334 term browser browse the term
Definition:A naphthoic acid that is 6-phenylnaphthylene-2-carboxyic acid in which the phenyl substituent has been substituted at positions 3 and 4 by adamant-1-yl and hydroxy groups, respectively. It acts as a selective agonist of retinoic acid receptor (RAR)gamma and induces cell cycle arrest and apoptosis in various cancer cells.
Synonyms:exact_synonym: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid
 related_synonym: 6-[4-hydroxy-3-(tricyclo[,7)]dec-1-yl)phenyl]-2-naphthalenecarboxylic acid;   6-[4-hydroxy-3-(tricyclo[,7)]dec-1-yl)phenyl]naphthalene-2-carboxylic acid;   AHPN;   Apoptosis Activator VI;   CD-437;   Formula=C27H26O3;   InChI=1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30);   InChIKey=LDGIHZJOIQSHPB-UHFFFAOYSA-N;   SMILES=C1C2(CC3CC(CC1C3)C2)C4=C(C=CC(=C4)C5=CC=C6C(=C5)C=CC(=C6)C(=O)O)O
 xref: CAS:125316-60-1;   LINCS:LSM-6237;   PMID:10942519;   PMID:11526443;   PMID:12566985;   PMID:12581872;   PMID:17474084;   PMID:18936944;   PMID:22446330;   PMID:9846184;   Reaxys:7445028

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adapalene term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cd1d1 CD1d1 molecule increases expression ISO Adapalene results in increased expression of CD1D protein CTD PMID:17518990 NCBI chr 2:172,423,582...172,427,089
Ensembl chr 2:172,423,582...172,427,089
JBrowse link
G Crabp2 cellular retinoic acid binding protein 2 increases expression ISO Adapalene results in increased expression of CRABP2 mRNA CTD PMID:8396608 PMID:9990415 NCBI chr 2:173,417,004...173,421,352
Ensembl chr 2:173,416,857...173,421,379
JBrowse link
G Il10 interleukin 10 decreases expression ISO Adapalene results in decreased expression of IL10 protein CTD PMID:17518990 NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
JBrowse link
G Rarg retinoic acid receptor, gamma affects response to substance ISO RARG protein affects the susceptibility to Adapalene CTD PMID:9990413 NCBI chr 7:133,367,833...133,390,301
Ensembl chr 7:133,367,833...133,390,177
JBrowse link
G Slc22a2 solute carrier family 22 member 2 multiple interactions ISO Adapalene inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268
JBrowse link
G Tlr2 toll-like receptor 2 decreases expression ISO Adapalene results in decreased expression of TLR2 protein CTD PMID:17518990 NCBI chr 2:169,200,620...169,206,819
Ensembl chr 2:169,197,419...169,206,630
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      biological role 19769
        biochemical role 19389
          apoptosis inducer 13236
            CD437 6
              adapalene 6
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      carboxylic acid 18373
                                        aromatic carboxylic acid 11710
                                          naphthoic acid 43
                                            CD437 6
                                              adapalene 6
paths to the root