This structer was produced by RasMol,
and stucked by GifBuilder (Yves Piguet, 1997)
ORTEP-III (Burnett, 1996) drawing
Wortmannin is isolated from Penicillium wortmanni and is a potent inhibitor
of phosphatidylinositol 3-kinase (PI 3-kinase). The electrophilic 21-site
makes a covalent linkage with the enzyme and the inhibition of PI 3-kinase
is irreversible. PI 3-kinase mediates several intracellular signaling
pathways, and wortmannin has been focused as a probe to understand the
structural requirements necessary for PI 3-kinase inhibition. Two types
of structure has been reported for wortmannin; one is orthorhombic crystal
and space group P2121212, the other is a 21-methylated analogue and
monoclinic, P21. This crystal is a polymorphic with monoclinic C2.
When the minimum van der Waals radii for carbon, oxygen and hydrogen atoms are considered approximately as 1.5, 1.7 and 1.2 Ang respectively, a short contact is found at C21...O21. The distance between H21 and O21 atoms is about 0.5 Ang below the sum of the van der Waals radii of hydrogen and oxygen (=2.7 Ang. and it could be defined as the C-H...O hydrogen bond.
Paper: Polymorphism and C-H...O interactions of Wortmannin, a Phosphatidylinositol 3-Kinase Inhibitor
Mitsunobu DOI, Toshimasa ISHIDA, Akira TERASHIMA, Taizo TANIGUCHI, Masahiro SASAKI and Chikako TANAKA
Analytical Sciences (1998) 14, 1191-2.
|formula||C9 H10 F N O4 + H2O|
|c (Ang)||13.065(4)||size (mm)||0.5x0.09x0.09|
|alpha (deg)||90.0||Dx (g/ml)||1.553|
|Flack||device type||Rigaku AFC5R/RU-200|
|R_factor_all||0.0592||theta (deg.)||4.33 - 65.58|
|R_factor_gt||0.0453||total reflections||3239 include Friedel pairs|
|wR_factor_ref||0.1321||reflections(obs)||1393 .gt. 2sigma(I)|