plumbagin   Click here for help

GtoPdb Ligand ID: 7003

Synonyms: RTK1
PDB Ligand
Comment: Plumbagin is a genotoxic and mutagenic plant-derived toxin. It has some activity as a histone acetyltransferase (HAT) inhibitor, however a 2017 article by Dahlin et al. suggests that the thiol-reactivity of plumbagin brings in to question its HAT inhibitor activity [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 54.37
Molecular weight 188.05
XLogP 1.22
No. Lipinski's rules broken 0
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Canonical SMILES CC1=CC(=O)c2c(C1=O)cccc2O
Isomeric SMILES CC1=CC(=O)c2c(C1=O)cccc2O
InChI InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
1. 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]
2. Ravindra KC, Selvi BR, Arif M, Reddy BA, Thanuja GR, Agrawal S, Pradhan SK, Nagashayana N, Dasgupta D, Kundu TK. (2009)
Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin.
J Biol Chem, 284 (36): 24453-64. [PMID:19570987]