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

Classification

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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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Updated at
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