Clavaric acid

Clavaric acid is a triterpenoid produced by the mushroom Hypholoma sublateritium. Clavaric acid was discovered by Merck Research Laboratories in a random screening of natural extracts. Clavaric acid is a reversible farnesyltransferase inhibitor with an IC50 of 1.3 μM.[1][2]

Clavaric acid
Names
Other names
24, 25-Dihydroxy-2-(3-hydroxy-3-methylglutaryl)lanostan-3-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C36H58O8/c1-21(10-13-27(37)32(4,5)42)22-14-16-36(9)24-11-12-26-31(2,3)30(41)25(44-29(40)20-33(6,43)19-28(38)39)18-34(26,7)23(24)15-17-35(22,36)8/h21-22,25-27,37,42-43H,10-20H2,1-9H3,(H,38,39)/t21-,22-,25-,26+,27?,33?,34-,35-,36+/m1/s1
    Key: FNHDSKHVYPYDAZ-VCICWZRISA-N
  • C[C@H](CCC(C(C)(C)O)O)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(C[C@H](C(=O)C4(C)C)OC(=O)CC(C)(CC(=O)O)O)C)C)C
Properties
C36H58O8
Molar mass 618.852 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Lingham RB, Silverman KC, Jayasuriya H, Kim BM, Amo SE, Wilson FR, et al. (1998). "Clavaric acid and steroidal analogues as Ras- and FPP-directed inhibitors of human farnesyl-protein transferase". J Med Chem. 41 (23): 4492–501. doi:10.1021/jm980356+. PMID 9804689.
  2. Godio RP, Fouces R, Martín JF (2007). "A squalene epoxidase is involved in biosynthesis of both the antitumor compound clavaric acid and sterols in the basidiomycete H. sublateritium". Chem Biol. 14 (12): 1334–46. doi:10.1016/j.chembiol.2007.10.018. PMID 18096502.
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