cucurbitacin B   Click here for help

GtoPdb Ligand ID: 12432

Synonyms: (+)-Cucurbitacin B | Amarine | Datisca principle B
Comment: Cucurbitacin B is a natural product that is found in plants such as Begonia plebeja and Trichosanthes miyagii.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 138.2
Molecular weight 558.7
XLogP 2.73
No. Lipinski's rules broken 1
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Canonical SMILES CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@@H](C(=O)C4(C)C)O)[C@]3(C)C(=O)C[C@]12C)O)O
Isomeric SMILES CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O
InChI 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
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
[(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
Synonyms Click here for help
(+)-Cucurbitacin B | Amarine | Datisca principle B
Database Links Click here for help
Specialist databases
GPCRdb Ligand cucurbitacin B
Other databases
ChEMBL Ligand CHEMBL508185
GtoPdb PubChem SID 479821223
PubChem CID 5281316
Search Google for chemical match using the InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-N
Search Google for chemicals with the same backbone IXQKXEUSCPEQRD
UniChem Compound Search for chemical match using the InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-N
UniChem Connectivity Search for chemical match using the InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-N