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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 2:186,330,298...186,333,805
Ensembl chr 2:186,330,298...186,333,805
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 2:187,322,416...187,326,794
Ensembl chr 2:184,882,969...184,883,505
JBrowse link
G Il10 interleukin 10 decreases expression ISO Adapalene results in decreased expression of IL10 protein CTD PMID:17518990 NCBI chr13:47,738,933...47,743,392
Ensembl chr13:47,739,526...47,743,392
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 7:143,840,739...143,863,206
Ensembl chr 7:143,839,980...143,863,186
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 1:48,318,025...48,360,219
Ensembl chr 1:48,317,995...48,360,261
JBrowse link
G Tlr2 toll-like receptor 2 decreases expression ISO Adapalene results in decreased expression of TLR2 protein CTD PMID:17518990 NCBI chr 2:182,840,171...182,846,061
Ensembl chr 2:182,840,727...182,846,061
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        biochemical role 19313
          apoptosis inducer 10979
            CD437 6
              adapalene 6
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        aromatic carboxylic acid 10898
                                          naphthoic acid 42
                                            CD437 6
                                              adapalene 6
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