inobrodib   Click here for help

GtoPdb Ligand ID: 13063

Synonyms: CCS-1477 | CCS1477
PDB Ligand
Compound class: Synthetic organic
Comment: Inobrodib (CCS1477) is an orally active, potent, and selective inhibitor of the bromodomains of the E1A binding protein p300 and CREB binding protein (CBP) histone acetyltransferases (HATs) [1-2,5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 66.73
Molecular weight 534.6
XLogP 3.99
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC1=NOC(=C1C2=CC3=C(C=C2)N([C@H]4CC[C@@H](CC4)OC)C(=N3)[C@@H]5CCCC(=O)N5C6=CC=C(C(=C6)F)F)C
Isomeric SMILES O=C1N(C2=CC=C(F)C(F)=C2)[C@H](C3=NC4=CC(C5=C(C)ON=C5C)=CC=C4N3[C@H]6CC[C@H](OC)CC6)CCC1
InChI InChI=1S/C30H32F2N4O3/c1-17-29(18(2)39-34-17)19-7-14-26-25(15-19)33-30(36(26)20-8-11-22(38-3)12-9-20)27-5-4-6-28(37)35(27)21-10-13-23(31)24(32)16-21/h7,10,13-16,20,22,27H,4-6,8-9,11-12H2,1-3H3/t20-,22-,27-/m0/s1
InChI Key SKDNDJWEBPQKCS-CLHVYKLBSA-N
References
1. He ZX, Wei BF, Zhang X, Gong YP, Ma LY, Zhao W. (2021)
Current development of CBP/p300 inhibitors in the last decade.
Eur J Med Chem, 209: 112861. [PMID:33045661]
2. Liu R, Yang H, Chen Z, Zhou K, Shi Q, Li J, Huang Y, Huang X, Li Y. (2022)
Design, synthesis and biological evaluation of (R)-5-methylpyrrolidin-2-ones as p300 bromodomain inhibitors with Anti-Tumor activities in multiple tumor lines.
Bioorg Chem, 124: 105803. [PMID:35439627]
3. Nicosia L, Spencer GJ, Brooks N, Amaral FMR, Basma NJ, Chadwick JA, Revell B, Wingelhofer B, Maiques-Diaz A, Sinclair O et al.. (2023)
Therapeutic targeting of EP300/CBP by bromodomain inhibition in hematologic malignancies.
Cancer Cell, 41 (12): 2136-2153.e13. [PMID:37995682]
4. Rasool RU, Natesan R, Asangani IA. (2021)
Toppling the HAT to Treat Lethal Prostate Cancer.
Cancer Discov, 11 (5): 1011-1013. [PMID:33947717]
5. Welti J, Sharp A, Brooks N, Yuan W, McNair C, Chand SN, Pal A, Figueiredo I, Riisnaes R, Gurel B et al.. (2021)
Targeting the p300/CBP Axis in Lethal Prostate Cancer.
Cancer Discov, 11 (5): 1118-1137. [PMID:33431496]
6. Xiang Q, Wang C, Wu T, Zhang C, Hu Q, Luo G, Hu J, Zhuang X, Zou L, Shen H et al.. (2022)
Design, Synthesis, and Biological Evaluation of 1-(Indolizin-3-yl)ethan-1-ones as CBP Bromodomain Inhibitors for the Treatment of Prostate Cancer.
J Med Chem, 65 (1): 785-810. [PMID:34962793]