ABT-737   

GtoPdb Ligand ID: 8320

Synonyms: ABT 737 | ABT737 | compound 2 [PMID 17256834] [2]
Compound class: Synthetic organic
Comment: ABT-737 is an antagonist of prosurvival Bcl-2 family proteins [2], but has poor aqueous solubility.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 161.81
Molecular weight 812.26
XLogP 9.85
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CN(CCC(Nc1ccc(cc1[N+](=O)[O-])S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)Cc1ccccc1c1ccc(cc1)Cl)CSc1ccccc1)C
Isomeric SMILES CN(CC[C@@H](Nc1ccc(cc1[N+](=O)[O-])S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)Cc1ccccc1c1ccc(cc1)Cl)CSc1ccccc1)C
InChI InChI=1S/C42H45ClN6O5S2/c1-46(2)23-22-35(30-55-37-9-4-3-5-10-37)44-40-21-20-38(28-41(40)49(51)52)56(53,54)45-42(50)32-14-18-36(19-15-32)48-26-24-47(25-27-48)29-33-8-6-7-11-39(33)31-12-16-34(43)17-13-31/h3-21,28,35,44H,22-27,29-30H2,1-2H3,(H,45,50)/t35-/m1/s1
InChI Key HPLNQCPCUACXLM-PGUFJCEWSA-N
References
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. Bruncko M, Oost TK, Belli BA, Ding H, Joseph MK, Kunzer A, Martineau D, McClellan WJ, Mitten M, Ng SC et al.. (2007)
Studies leading to potent, dual inhibitors of Bcl-2 and Bcl-xL.
J. Med. Chem., 50 (4): 641-62. [PMID:17256834]
3. Green DR, Evan GI. (2002)
A matter of life and death.
Cancer Cell, 1 (1): 19-30. [PMID:12086884]
4. Jain HV, Meyer-Hermann M. (2011)
The molecular basis of synergism between carboplatin and ABT-737 therapy targeting ovarian carcinomas.
Cancer Res., 71 (3): 705-15. [PMID:21169413]
5. Lheureux S, N'Diaye M, Blanc-Fournier C, Dugué AE, Clarisse B, Dutoit S, Giffard F, Abeilard E, Briand M, Labiche A et al.. (2015)
Identification of predictive factors of response to the BH3-mimetic molecule ABT-737: an ex vivo experiment in human serous ovarian carcinoma.
Int. J. Cancer, 136 (5): E340-50. [PMID:25066666]
6. Tian BP, Xia LX, Bao ZQ, Zhang H, Xu ZW, Mao YY, Cao C, Che LQ, Liu JK, Li W et al.. (2017)
Bcl-2 inhibitors reduce steroid-insensitive airway inflammation.
J. Allergy Clin. Immunol., 140 (2): 418-430. [PMID:28043871]
7. Witham J, Valenti MR, De-Haven-Brandon AK, Vidot S, Eccles SA, Kaye SB, Richardson A. (2007)
The Bcl-2/Bcl-XL family inhibitor ABT-737 sensitizes ovarian cancer cells to carboplatin.
Clin. Cancer Res., 13 (23): 7191-8. [PMID:18056200]