Clavaric acid

Clavaric acid is a lanostane type steroid produced by the mushroom Hypholoma lateritium. 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)	Interactive image
ChEBI	CHEBI:219348
ChEMBL	ChEMBL452658
ChemSpider	5293553
PubChem CID	6918349
CompTox Dashboard (EPA)	DTXSID001045451
InChI 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
SMILES 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
Chemical formula	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.