LIPID MAPS

Structure Database (LMSD)

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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)

LM ID

LMST01100007

Formula

C₃₉H₆₀O₁₁

Exact Mass

Calculate m/z

704.413565

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

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

DOI: 10.1186/1860-5397-3-3

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]