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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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-
InChI Key HEKJYZZSCQBJGB-UNOMPAQXSA-N
References
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]