tretinoin   

GtoPdb Ligand ID: 2644

Synonyms: all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
tretinoin is an approved drug (FDA (1995))
Comment: Tretinoin is a naturally occurring derivative of vitamin A (retinoic acid) and as such is an agonist at the retinoic acid receptors. Tretinoin binds to α, β, and γ isoforms of the retinoic acid receptor. Retionoids are important regulators of cell reproduction, proliferation, and differentiation.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Isomeric SMILES C/C(=C\C=C\C(=C\C(=O)O)\C)/C=C/C1=C(C)CCCC1(C)C
InChI 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+
InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N
References
1. Allenby G, Bocquel MT, Saunders M, Kazmer S, Speck J, Rosenberger M, Lovey A, Kastner P, Grippo JF, Chambon P. (1993)
Retinoic acid receptors and retinoid X receptors: interactions with endogenous retinoic acids.
Proc. Natl. Acad. Sci. U.S.A., 90 (1): 30-4. [PMID:8380496]
2. Charton J, Deprez-Poulain R, Hennuyer N, Tailleux A, Staels B, Deprez B. (2009)
Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.
Bioorg. Med. Chem. Lett., 19 (2): 489-92. [PMID:19058965]
3. Keidel S, LeMotte P, Apfel C. (1994)
Different agonist- and antagonist-induced conformational changes in retinoic acid receptors analyzed by protease mapping.
Mol. Cell. Biol., 14 (1): 287-98. [PMID:8264595]
4. Klaholz BP, Mitschler A, Moras D. (2000)
Structural basis for isotype selectivity of the human retinoic acid nuclear receptor.
J. Mol. Biol., 302 (1): 155-70. [PMID:10964567]
5. Nagy L, Thomázy VA, Shipley GL, Fésüs L, Lamph W, Heyman RA, Chandraratna RA, Davies PJ. (1995)
Activation of retinoid X receptors induces apoptosis in HL-60 cell lines.
Mol. Cell. Biol., 15 (7): 3540-51. [PMID:7791761]
6. Richieri GV, Ogata RT, Zimmerman AW, Veerkamp JH, Kleinfeld AM. (2000)
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
Biochemistry, 39 (24): 7197-204. [PMID:10852718]
7. Shaw N, Elholm M, Noy N. (2003)
Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta.
J. Biol. Chem., 278 (43): 41589-92. [PMID:12963727]
8. Stehlin-Gaon C, Willmann D, Zeyer D, Sanglier S, Van Dorsselaer A, Renaud JP, Moras D, Schüle R. (2003)
All-trans retinoic acid is a ligand for the orphan nuclear receptor ROR beta.
Nat. Struct. Biol., 10 (10): 820-5. [PMID:12958591]
9. Thacher SM, Vasudevan J, Chandraratna RA. (2000)
Therapeutic applications for ligands of retinoid receptors.
Curr. Pharm. Des., 6 (1): 25-58. [PMID:10637371]
10. Zhou XE, Suino-Powell KM, Xu Y, Chan CW, Tanabe O, Kruse SW, Reynolds R, Engel JD, Xu HE. (2011)
The orphan nuclear receptor TR4 is a vitamin A-activated nuclear receptor.
J. Biol. Chem., 286 (4): 2877-85. [PMID:21068381]