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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 402
    role 402
      chemical role 328
        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
            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 402
    subatomic particle 402
      composite particle 402
        hadron 402
          baryon 402
            nucleon 402
              atomic nucleus 402
                atom 402
                  main group element atom 395
                    p-block element atom 395
                      carbon group element atom 384
                        carbon atom 383
                          organic molecular entity 383
                            organic group 313
                              organic divalent group 312
                                organodiyl group 312
                                  carbonyl group 312
                                    carbonyl compound 312
                                      carboxylic acid 276
                                        monocarboxylic acid 92
                                          alpha,beta-unsaturated monocarboxylic acid 7
                                            retinoic acid 7
                                              all-trans-retinoic acid 7
                                                1-O-all-trans-retinoyl-beta-glucuronic acid 0
                                                4-hydroxyphenyl retinamide 0
                                                5,6-epoxyretinoic 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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