C646   Click here for help

GtoPdb Ligand ID: 7004

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The structure represented here was drawn from [1], with our structure showing the charges on the nitro functional group. However, this molecule is drawn with one unspecified bond in [3] which matches PubChem CID 2871948.
A 2017 article by Dahlin et al. suggests that the thiol-reactivity of C464 brings in to question its activity as a selective HAT inhibitor [2], and this is somewhat confirmed by evidence of histone deacetylase inhibition reported in [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 126.25
Molecular weight 445.13
XLogP 4.84
No. Lipinski's rules broken 0
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Canonical SMILES CC1=NN(C(=O)C1=Cc1ccc(o1)c1cc(C)c(cc1[N+](=O)[O-])C)c1ccc(cc1)C(=O)O
Isomeric SMILES CC1=NN(C(=O)/C/1=C\c1ccc(o1)c1cc(C)c(cc1[N+](=O)[O-])C)c1ccc(cc1)C(=O)O
InChI InChI=1S/C24H19N3O6/c1-13-10-20(21(27(31)32)11-14(13)2)22-9-8-18(33-22)12-19-15(3)25-26(23(19)28)17-6-4-16(5-7-17)24(29)30/h4-12H,1-3H3,(H,29,30)/b19-12-
1. Bowers EM, Yan G, Mukherjee C, Orry A, Wang L, Holbert MA, Crump NT, Hazzalin CA, Liszczak G, Yuan H et al.. (2010)
Virtual ligand screening of the p300/CBP histone acetyltransferase: identification of a selective small molecule inhibitor.
Chem Biol, 17 (5): 471-82. [PMID:20534345]
2. Dahlin JL, Nelson KM, Strasser JM, Barsyte-Lovejoy D, Szewczyk MM, Organ S, Cuellar M, Singh G, Shrimp JH, Nguyen N et al.. (2017)
Assay interference and off-target liabilities of reported histone acetyltransferase inhibitors.
Nat Commun, 8 (1): 1527. [PMID:29142305]
3. Dekker FJ, van den Bosch T, Martin NI. (2014)
Small molecule inhibitors of histone acetyltransferases and deacetylases are potential drugs for inflammatory diseases.
Drug Discov Today, 19 (5): 654-660. [PMID:24269836]
4. van den Bosch T, Boichenko A, Leus NGJ, Ourailidou ME, Wapenaar H, Rotili D, Mai A, Imhof A, Bischoff R, Haisma HJ et al.. (2016)
The histone acetyltransferase p300 inhibitor C646 reduces pro-inflammatory gene expression and inhibits histone deacetylases.
Biochem Pharmacol, 102: 130-140. [PMID:26718586]