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
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Compound class Natural product or derivative
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Database Links Click here for help
CAS Registry No. 78824-30-3
GtoPdb PubChem SID 178103580
PubChem CID 174159
Search Google for chemical match using the InChIKey DTTONLKLWRTCAB-SMDXAGPFSA-N
Search Google for chemicals with the same backbone DTTONLKLWRTCAB
UniChem Compound Search for chemical match using the InChIKey DTTONLKLWRTCAB-SMDXAGPFSA-N
UniChem Connectivity Search for chemical match using the InChIKey DTTONLKLWRTCAB-SMDXAGPFSA-N