Structure Database (LMSD)

Common Name
Melianthusigenin
Systematic Name
(1β,3β,5β)-1,3,5-[(1R)-ethylidynetris(oxy)]-14β-hydroxy-19β-acetoxy-bufa-20,22-dienolide
Synonyms
LM ID
LMST01130052
Formula
C28H36O8
Exact Mass
Calculate m/z
500.24102
Sum Composition
ST 28:7;O8
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Bufanolides and derivatives [ST0113]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Melianthus major (#85230)
Magnoliopsida (#3398)
Cytotoxic Bufadienolides from the Leaves of Melianthus major.,
J Nat Prod, 2020
Pubmed ID: 32663024

String Representations

InChiKey (Click to copy)
RRDZJCCZVWCHID-NSRWUMAOSA-N
InChi (Click to copy)
InChI=1S/C28H36O8/c1-16(29)33-15-27-20-6-9-24(2)19(17-4-5-23(30)32-14-17)8-11-28(24,31)21(20)7-10-26(27)13-18-12-22(27)35-25(3,34-18)36-26/h4-5,14,18-22,31H,6-13,15H2,1-3H3/t18-,19+,20-,21+,22+,24+,25+,26-,27-,28-/m0/s1
SMILES (Click to copy)
[C@H]12O[C@]3(C)O[C@@]4(CC[C@]5([H])[C@]([H])(CC[C@]6(C)[C@@]([H])(C7C=CC(=O)OC=7)CC[C@]56O)[C@@]14COC(=O)C)C[C@@H](O3)C2

Other Databases

PubChem CID
171120531

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 8
Aromatic Rings 1
Rotatable Bonds 4
Van der Waals Molecular Volume 451.50
Topological Polar Surface Area 110.64
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 6.26
Molar Refractivity 128.88

Admin

Created at
16th Jul 2020
Updated at
16th Jul 2020