I-CBP112   Click here for help

GtoPdb Ligand ID: 8236

Compound class: Synthetic organic
Comment: I-CBP112 is an inhibitor of the bromodomain-containing proteins CREB binding protein (CREBBP) and E1A binding protein p300 (EP300) and was developed by the Structural Genomics Consortium (SGC) [3]. The bromodomains facilitate binding of these proteins to acetylated lysine residues on histones and other proteins [4], interactions which underlie the function of these two transctiptional co-activators in the control of DNA replication and repair, cell growth, transformation, and development [1-2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 60.47
Molecular weight 468.26
XLogP 3.53
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC(=O)N1CCOc2c(C1)cc(cc2OCC1CCCN(C1)C)c1ccc(c(c1)OC)OC
Isomeric SMILES CCC(=O)N1CCOc2c(C1)cc(cc2OC[C@H]1CCCN(C1)C)c1ccc(c(c1)OC)OC
InChI InChI=1S/C27H36N2O5/c1-5-26(30)29-11-12-33-27-22(17-29)13-21(20-8-9-23(31-3)24(14-20)32-4)15-25(27)34-18-19-7-6-10-28(2)16-19/h8-9,13-15,19H,5-7,10-12,16-18H2,1-4H3/t19-/m0/s1
InChI Key YKNAKDFZAWQEEO-IBGZPJMESA-N
References
1. Iyer NG, Ozdag H, Caldas C. (2004)
p300/CBP and cancer.
Oncogene, 23 (24): 4225-31. [PMID:15156177]
2. Kalkhoven E. (2004)
CBP and p300: HATs for different occasions.
Biochem. Pharmacol., 68 (6): 1145-55. [PMID:15313412]
3. SGC. 
I-CBP112 - a CREBBP/EP300-selective chemical probe.
Accessed on 03/03/2015. Modified on 03/03/2015. thesgc.org, http://www.thesgc.org/chemical-probes/ICBP112
4. Zeng L, Zhang Q, Gerona-Navarro G, Moshkina N, Zhou MM. (2008)
Structural basis of site-specific histone recognition by the bromodomains of human coactivators PCAF and CBP/p300.
Structure, 16 (4): 643-52. [PMID:18400184]