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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/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.
Term:all-trans-retinoic acid
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Accession:CHEBI:15367 term browser browse the term
Definition:A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.
Synonyms:exact_synonym: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
 related_synonym: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid;   (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;   3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid;   3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid;   3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid;   AGN 100335;   Acide retinoique (French);   Altreno;   Atralin;   Avita;   Betarretin;   Biacna;   Cordes vas;   Dermairol;   Formula=C20H28O2;   InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+;   InChIKey=SHGAZHPCJJPHSC-YCNIQYBTSA-N;   RETINOIC ACID;   Refissa;   Renova;   Retin-A;   Retisol-A;   Ro 1-5488;   SMILES=CC(\\C=C\\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(O)=O;   Stieva-A;   Tretin M;   Tri-luma;   Veltin;   Vesanoid;   Vitamin A acid;   all-(E)-Retinoic acid;   all-trans-Tretinoin;   all-trans-Vitamin A acid;   all-trans-Vitamin A1 acid;   all-trans-beta-Retinoic acid;   beta-Retinoic acid;   trans-Retinoic acid;   tretinoin;   tretinoina;   tretinoine;   tretinoinum
 alt_id: CHEBI:45376;   CHEBI:8815
 xref: Beilstein:2057223;   CAS:302-79-4;   DrugBank:DB00755;   Drug_Central:2722;   FooDB:FDB022710;   HMDB:HMDB0001852;   KEGG:C00777;   KEGG:D00094;   LIPID_MAPS_instance:LMPR01090019
 xref_mesh: MESH:D014212
 xref: PDBeChem:REA;   PMID:10022884;   PMID:10970886;   PMID:11073974;   PMID:11214352;   PMID:11332619;   PMID:11343416;   PMID:11437362;   PMID:11556813;   PMID:11722649;   PMID:11896294;   PMID:11904404;   PMID:12958591;   PMID:14581379;   PMID:14605492;   PMID:14627725;   PMID:14704332;   PMID:14705145;   PMID:14978018;   PMID:15194426;   PMID:15318809;   PMID:15327395;   PMID:15359008;   PMID:15376324;   PMID:15476854;   PMID:15537748;   PMID:15539337;   PMID:15675886;   PMID:15839997;   PMID:16569247;   PMID:16685080;   PMID:16688769;   PMID:16720557;   PMID:16819260;   PMID:16847436;   PMID:16920920;   PMID:17073551;   PMID:17166212;   PMID:17204142;   PMID:17447762;   PMID:18052213;   PMID:18085670;   PMID:18162363;   PMID:18183617;   PMID:18318655;   PMID:18322276;   PMID:18400206;   PMID:18404486;   PMID:18440196;   PMID:18678272;   PMID:18800767;   PMID:18819820;   PMID:18977311;   PMID:19018099;   PMID:19112091;   PMID:19144697;   PMID:19427305;   PMID:19587328;   PMID:19597529;   PMID:19814868;   PMID:19841174;   PMID:21898109;   PMID:21924320;   PMID:21993673;   PMID:22134377;   PMID:22177959;   PMID:22180426;   PMID:22244299;   PMID:22261335;   PMID:22428994;   PMID:22514600;   PMID:22532966;   PMID:22534100;   PMID:22538278;   PMID:22741806;   PMID:27759097;   PMID:29492455;   PMID:33662750;   PMID:33820492;   PMID:34050114;   PMID:34050360;   PMID:34091189;   PMID:7501014;   PMID:7704533;   PMID:7961949;   Reaxys:2057223;   Wikipedia:Retinoic_acid;   Wikipedia:Tretinoin
 cyclic_relationship: is_conjugate_acid_of CHEBI:35291


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all-trans-retinoic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G CASP3 caspase 3 increases activity EXP Tretinoin results in increased activity of CASP3 protein CTD PMID:16953078 NCBI chr16:45,920,074...45,940,507
Ensembl chr16:45,920,071...45,940,505 		JBrowse link
G CLDN1 claudin 1 multiple interactions
increases expression		 EXP CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of CLDN1 mRNA]
Tretinoin results in increased expression of CLDN1 mRNA; Tretinoin results in increased expression of CLDN1 protein		 CTD PMID:17035595 NCBI chr34:22,303,058...22,319,101
Ensembl chr34:22,303,850...22,319,033 		JBrowse link
G CLDN4 claudin 4 increases expression
multiple interactions		 EXP Tretinoin results in increased expression of CLDN4 mRNA; Tretinoin results in increased expression of CLDN4 protein
CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of CLDN4 mRNA]		 CTD PMID:17035595 NCBI chr 6:6,492,706...6,506,750
Ensembl chr 6:6,493,513...6,494,145 		JBrowse link
G CYP26A1 cytochrome P450 family 26 subfamily A member 1 increases degradation
multiple interactions		 EXP CYP26A1 protein results in increased degradation of Tretinoin
CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of CLDN1 mRNA]; CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of CLDN4 mRNA]; CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of OCLN mRNA]; CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of TJP1 mRNA]		 CTD PMID:17035595 NCBI chr28:7,423,955...7,432,359
Ensembl chr28:7,428,772...7,432,370 		JBrowse link
G NOS3 nitric oxide synthase 3 increases expression EXP Tretinoin results in increased expression of NOS3 mRNA; Tretinoin results in increased expression of NOS3 protein CTD PMID:17267746 NCBI chr16:15,054,196...15,072,454
Ensembl chr16:15,011,344...15,072,277 		JBrowse link
G OCLN occludin multiple interactions
increases expression		 EXP CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of OCLN mRNA]
Tretinoin results in increased expression of OCLN mRNA; Tretinoin results in increased expression of OCLN protein		 CTD PMID:17035595 NCBI chr 2:54,500,299...54,545,430
Ensembl chr 2:54,500,299...54,545,430 		JBrowse link
G TJP1 tight junction protein 1 increases expression
multiple interactions		 EXP Tretinoin results in increased expression of TJP1 mRNA; Tretinoin results in increased expression of TJP1 protein
CYP26A1 protein inhibits the reaction [Tretinoin results in increased expression of TJP1 mRNA]		 CTD PMID:17035595 NCBI chr 3:38,997,122...39,076,617
Ensembl chr 3:38,997,076...39,241,574 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 494
    role 501
      chemical role 420
        antioxidant 43
          all-trans-retinoic acid 7
            1-O-all-trans-retinoyl-beta-glucuronic acid 0
            4-hydroxyphenyl retinamide 0
            5,6-epoxyretinoic acid + 0
            SR11302 0
            all-trans-13,14-dihydroretinoic acid + 0
            all-trans-16-hydroxyretinoic acid 0
            all-trans-18-hydroxyretinoic acid 0
            all-trans-3,4-didehydroretinoic acid 0
            all-trans-4,16-dihydroxyretinoic acid 0
            all-trans-4,18-dihydroxyretinoic acid 0
            all-trans-4-hydroxyretinoic acid + 0
            all-trans-4-oxo-16-hydroxyretinoic acid 0
            all-trans-4-oxo-18-hydroxyretinoic acid 0
            all-trans-4-oxoretinoic acid + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 494
    subatomic particle 494
      composite particle 494
        hadron 501
          baryon 494
            nucleon 494
              atomic nucleus 494
                atom 494
                  main group element atom 487
                    main group molecular entity 487
                      s-block molecular entity 438
                        hydrogen molecular entity 437
                          hydrides 362
                            organic hydride 71
                              organic fundamental parent 71
                                hydrocarbon 49
                                  terpene 20
                                    terpenoid 20
                                      diterpenoid 15
                                        retinoid 8
                                          vitamin A 7
                                            all-trans-retinoic acid 7
                                              1-O-all-trans-retinoyl-beta-glucuronic acid 0
                                              4-hydroxyphenyl retinamide 0
                                              5,6-epoxyretinoic acid + 0
                                              SR11302 0
                                              all-trans-13,14-dihydroretinoic acid + 0
                                              all-trans-16-hydroxyretinoic acid 0
                                              all-trans-18-hydroxyretinoic acid 0
                                              all-trans-3,4-didehydroretinoic acid 0
                                              all-trans-4,16-dihydroxyretinoic acid 0
                                              all-trans-4,18-dihydroxyretinoic acid 0
                                              all-trans-4-hydroxyretinoic acid + 0
                                              all-trans-4-oxo-16-hydroxyretinoic acid 0
                                              all-trans-4-oxo-18-hydroxyretinoic acid 0
                                              all-trans-4-oxoretinoic acid + 0
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