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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 20089
    role 20042
      biological role 20011
        biochemical role 19671
          apoptosis inducer 13408
            CD437 6
              adapalene 6
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic group 18988
                              organic divalent group 18950
                                organodiyl group 18974
                                  carbonyl group 18903
                                    carbonyl compound 18925
                                      carboxylic acid 18597
                                        aromatic carboxylic acid 11811
                                          naphthoic acid 45
                                            CD437 6
                                              adapalene 6
paths to the root