Structure Database (LMSD)
Common Name
Cucurbitacin B
Systematic Name
Synonyms
LM ID
LMST01010104
Formula
Exact Mass
Calculate m/z
558.319271
Sum Composition
Status
Curated
3D model of Cucurbitacin B
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Cucurbitacin B is a plant-derived triterpene that has the classic four-ring structure of mammalian steroids. It has diverse effects on mammalian cells, most notably inducing cell cycle arrest or apoptosis in a range of cancer cell lines.1,2,3 Cucurbitacin B inhibits the growth of several breast cancer cell lines (IC50s = 18-50 nM).4 It suppresses the growth of tumors developed from MDA-MB-231 and 4T-1 breast cancer cells in mice.4 Cucurbitacin B blocks the inflammatory response of macrophages treated with lipopolysaccharide.5 In Drosophila, it serves as an ecdysteroid receptor antagonist (Kd = 5 µM).6
This information has been provided by Cayman Chemical
References
3. Dinan, L., Whiting, P., Girault, J.P., et al. Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid recepto. Biochem. J. 327( Pt 3)(Pt 3), 643-650 (1997).
String Representations
InChiKey (Click to copy)
IXQKXEUSCPEQRD-DKRGWESNSA-N
InChi (Click to copy)
InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
SMILES (Click to copy)
[C@@]12(C)C[C@H]([C@]([H])([C@](O)(C)C(=O)/C=C/C(C)(C)OC(=O)C)[C@@]1(C)CC([C@@]1(C)[C@]3([H])C[C@@H](C(=O)C(C)(C)C3=CC[C@@]21[H])O)=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
40
Rings
4
Aromatic Rings
0
Rotatable Bonds
6
Van der Waals Molecular Volume
567.20
Topological Polar Surface Area
138.20
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
8
logP
4.64
Molar Refractivity
149.81
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Created at
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Updated at
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