Structure Database (LMSD)
Common Name
cimicifoetiside B
Systematic Name
3β-(2-O-acetyl-α-L-arabinopyranosyloxy)-15α-hydroxy-16β,23R:16α,24S-diepoxy-9β,19-cyclolanostan-25-yl acetate
Synonyms
- (23R,24S)-25-acetoxy-15alpha-hydroxy-16beta,23:16alpha,24-diepoxy-9beta,19-cyclolanostan-3beta-yl 2-O-acetyl-alpha-L-arabinopyranoside
- 25-O-acetylcimigenol 3-O-(2-O-acetyl-alpha-L-arabinopyranoside)
3D model of cimicifoetiside B
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Main
Classification
Category
Main Class
Sub Class
String Representations
InChiKey (Click to copy)
DEEGQLBLXWGMCY-HNGFUVDTSA-N
InChi (Click to copy)
InChI=1S/C39H60O11/c1-19-16-23-30(34(6,7)48-21(3)41)50-39(49-23)29(19)35(8)14-15-38-18-37(38)13-12-26(47-31-28(46-20(2)40)27(43)22(42)17-45-31)33(4,5)24(37)10-11-25(38)36(35,9)32(39)44/h19,22-32,42-44H,10-18H2,1-9H3/t19-,22+,23-,24+,25+,26+,27+,28-,29-,30+,31+,32-,35-,36-,37-,38+,39+/m1/s1
SMILES (Click to copy)
C1C[C@]2([H])[C@@]3(C[C@]43CC[C@H](O[C@@H]3OC[C@H](O)[C@H](O)[C@H]3OC(C)=O)C(C)(C)[C@]14[H])CC[C@@]1(C)[C@@]2(C)[C@@H](O)[C@]23O[C@H](C(C)(C)OC(C)=O)[C@]([H])(O2)C[C@@H](C)[C@]13[H]
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Actaea cimicifuga
(#64032)
Magnoliopsida
(#3398)
Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells.,
Beilstein J Org Chem, 2007
Beilstein J Org Chem, 2007
Pubmed ID:
17266751
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
50
Rings
8
Aromatic Rings
0
Rotatable Bonds
7
Van der Waals Molecular Volume
675.79
Topological Polar Surface Area
156.42
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
11
logP
7.41
Molar Refractivity
183.55
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Updated at
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