garcinol   Click here for help

GtoPdb Ligand ID: 7001

Comment: The is some ambiguity as to the exact stereochemistry of garcinol, with several representations of the structure listed on PubChem. It has been ascribed activity as a histone acetyltransferase (HAT) inhibitor. However, a 2017 article by Dahlin et al. suggests that the garcinol non-specifically perturbs biological assays, bringing in to question its HAT inhibitor activity [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 111.9
Molecular weight 602.36
XLogP 10.52
No. Lipinski's rules broken 1
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Canonical SMILES CC(=CCC12C(=O)C(=C(c3ccc(c(c3)O)O)O)C(=O)C(C1=O)(CC(C(=C)C)CC=C(C)C)CC(C2(C)C)CC=C(C)C)C
Isomeric SMILES CC(=CC[C@]12C(=O)C(=C(c3ccc(c(c3)O)O)O)C(=O)[C@@](C1=O)(C[C@@H](C(=C)C)CC=C(C)C)C[C@H](C2(C)C)CC=C(C)C)C
InChI InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-41H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1
1. Balasubramanyam K, Altaf M, Varier RA, Swaminathan V, Ravindran A, Sadhale PP, Kundu TK. (2004)
Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression.
J Biol Chem, 279 (32): 33716-26. [PMID:15155757]
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]