hyperforin   Click here for help

GtoPdb Ligand ID: 2764

Comment: There is some ambiguity in the literature and online as to the exact structure of hyperforin. The structure shown here matches that on ChEBI as linked to above. The PubChem entry linked to above represents a different tautomer.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 71.44
Molecular weight 536.39
XLogP 9.45
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES CC(=CCCC1(C)C(CC=C(C)C)CC2(C(=O)C1(C(=O)C(C)C)C(=C(C2=O)CC=C(C)C)O)CC=C(C)C)C
Isomeric SMILES CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(C(=O)[C@]1(C(=O)C(C)C)C(=C(C2=O)CC=C(C)C)O)CC=C(C)C)C
InChI InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
1. Leuner K, Kazanski V, Müller M, Essin K, Henke B, Gollasch M, Harteneck C, Müller WE. (2007)
Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels.
FASEB J, 21 (14): 4101-11. [PMID:17666455]
2. Moore LB, Goodwin B, Jones SA, Wisely GB, Serabjit-Singh CJ, Willson TM, Collins JL, Kliewer SA. (2000)
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.
Proc Natl Acad Sci USA, 97 (13): 7500-2. [PMID:10852961]
3. Wentworth JM, Agostini M, Love J, Schwabe JW, Chatterjee VK. (2000)
St John's wort, a herbal antidepressant, activates the steroid X receptor.
J Endocrinol, 166 (3): R11-6. [PMID:10974665]