alitretinoin   Click here for help

GtoPdb Ligand ID: 2645

Synonyms: 9-cis-retinoic acid | Panretin® | Toctino®
Approved drug PDB Ligand
alitretinoin is an approved drug (FDA (1999), EMA (2000))
Comment: Alitretinoin is an important regulator of gene expression during normal growth and development, as well as in neoplasms. Alitretinoin is a retinoid receptor agonist.
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2D Structure
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Physico-chemical Properties
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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
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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-ZVCIMWCZSA-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. Heyman RA, Mangelsdorf DJ, Dyck JA, Stein RB, Eichele G, Evans RM, Thaller C. (1992)
9-cis retinoic acid is a high affinity ligand for the retinoid X receptor.
Cell, 68 (2): 397-406. [PMID:1310260]
3. Kagechika H, Kawachi E, Hashimoto Y, Himi T, Shudo K. (1988)
Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
J. Med. Chem., 31 (11): 2182-92. [PMID:3184125]
4. Keller C, Matzdorff AC, Kemkes-Matthes B. (1999)
Pharmacology of warfarin and clinical implications.
Semin. Thromb. Hemost., 25 (1): 13-6. [PMID:10327215]
5. 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]
6. Lala DS, Mukherjee R, Schulman IG, Koch SS, Dardashti LJ, Nadzan AM, Croston GE, Evans RM, Heyman RA. (1996)
Activation of specific RXR heterodimers by an antagonist of RXR homodimers.
Nature, 383 (6599): 450-3. [PMID:8837780]
7. Levin AA, Sturzenbecker LJ, Kazmer S, Bosakowski T, Huselton C, Allenby G, Speck J, Kratzeisen C, Rosenberger M, Lovey A. (1992)
9-cis retinoic acid stereoisomer binds and activates the nuclear receptor RXR alpha.
Nature, 355 (6358): 359-61. [PMID:1309942]
8. Mangelsdorf DJ, Borgmeyer U, Heyman RA, Zhou JY, Ong ES, Oro AE, Kakizuka A, Evans RM. (1992)
Characterization of three RXR genes that mediate the action of 9-cis retinoic acid.
Genes Dev., 6 (3): 329-44. [PMID:1312497]
9. 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]
10. 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]
11. Wallin R, Wajih N, Hutson SM. (2008)
VKORC1: a warfarin-sensitive enzyme in vitamin K metabolism and biosynthesis of vitamin K-dependent blood coagulation factors.
Vitam. Horm., 78: 227-46. [PMID:18374197]