Structure Database (LMSD)

O O O OH OH H H O O O OH HO H H
Common Name
cimicifoetiside A
Systematic Name
15α,25-dihydroxy-16β,23R:16α,24S-diepoxy-9β,19-cyclolanostan-3β-yl 2-O-acetyl-α-L-arabinopyranoside
Synonyms
  • cimigenol 3-O-(2-O-acetyl-alpha-L-arabinopyranoside)
LM ID
LMST01100006
Formula
C37H58O10
Exact Mass
Calculate m/z
662.403
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cycloartanols and derivatives [ST0110]

String Representations

InChiKey (Click to copy)
IGLQSEIGKREACI-VYWUFNEXSA-N
InChi (Click to copy)
InChI=1S/C37H58O10/c1-18-15-21-28(32(5,6)42)47-37(46-21)27(18)33(7)13-14-36-17-35(36)12-11-24(45-29-26(44-19(2)38)25(40)20(39)16-43-29)31(3,4)22(35)9-10-23(36)34(33,8)30(37)41/h18,20-30,39-42H,9-17H2,1-8H3/t18-,20+,21-,22+,23+,24+,25+,26-,27-,28+,29+,30-,33-,34-,35-,36+,37+/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)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
Pubmed ID: 17266751

Other Databases

CHEBI ID
37779
PubChem CID
16019999

Calculated Physicochemical Properties

Heavy Atoms 47
Rings 8
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 635.04
Topological Polar Surface Area 150.35
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 10
logP 6.84
Molar Refractivity 174.00

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Updated at
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