GtoPdb Ligand ID: 8319

Synonyms: ABT 263 | ABT-263
Compound class: Synthetic organic
Comment: Navitoclax is a potent and orally active BH3 mimetic which antagonises the action of Bcl-2 family proteins Bcl-2, Bcl-xL and Bcl-w [3]. This compound is the result of medicinal chemistry effort to increase aqueous solubility of the parent compound ABT-737.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 18
Topological polar surface area 170.42
Molecular weight 973.3
XLogP 10.69
No. Lipinski's rules broken 3
Canonical SMILES Clc1ccc(cc1)C1=C(CN2CCN(CC2)c2ccc(cc2)C(=O)NS(=O)(=O)c2ccc(c(c2)S(=O)(=O)C(F)(F)F)NC(CSc2ccccc2)CCN2CCOCC2)CC(CC1)(C)C
Isomeric SMILES Clc1ccc(cc1)C1=C(CN2CCN(CC2)c2ccc(cc2)C(=O)NS(=O)(=O)c2ccc(c(c2)S(=O)(=O)C(F)(F)F)N[C@@H](CSc2ccccc2)CCN2CCOCC2)CC(CC1)(C)C
InChI InChI=1S/C47H55ClF3N5O6S3/c1-46(2)20-18-42(34-8-12-37(48)13-9-34)36(31-46)32-55-22-24-56(25-23-55)39-14-10-35(11-15-39)45(57)53-65(60,61)41-16-17-43(44(30-41)64(58,59)47(49,50)51)52-38(19-21-54-26-28-62-29-27-54)33-63-40-6-4-3-5-7-40/h3-17,30,38,52H,18-29,31-33H2,1-2H3,(H,53,57)/t38-/m1/s1
1. Amundson SA, Myers TG, Scudiero D, Kitada S, Reed JC, Fornace Jr AJ. (2000)
An informatics approach identifying markers of chemosensitivity in human cancer cell lines.
Cancer Res., 60 (21): 6101-10. [PMID:11085534]
2. Green DR, Evan GI. (2002)
A matter of life and death.
Cancer Cell, 1 (1): 19-30. [PMID:12086884]
3. Park CM, Bruncko M, Adickes J, Bauch J, Ding H, Kunzer A, Marsh KC, Nimmer P, Shoemaker AR, Song X et al.. (2008)
Discovery of an orally bioavailable small molecule inhibitor of prosurvival B-cell lymphoma 2 proteins.
J. Med. Chem., 51 (21): 6902-15. [PMID:18841882]