Structure Database (LMSD)

Common Name
Withalongolide H
Systematic Name
27-O-[α-l-rhamnopyranosyl(1-4)]-β-d-glucopyranosyl 5β,6β:22R,26-diepoxyergosta-4β-hydroxy-2,24-diene-1,26-dione
Synonyms
  • 27-O-[alpha-l-rhamnopyranosyl(1-4)]-beta-d-glucopyranosylwithaferin A
LM ID
LMST01160074
Formula
C40H58O15
Exact Mass
Calculate m/z
778.377575
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Withanolides and derivatives [ST0116]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Physalis longifolia (#161495)
Magnoliopsida (#3398)
Cytotoxic withanolide constituents of Physalis longifolia.,
J Nat Prod, 2011
Pubmed ID: 22098611

String Representations

InChiKey (Click to copy)
KWSCHTSFNFDQSG-IPAGGVPOSA-N
InChi (Click to copy)
InChI=1S/C40H58O15/c1-16-12-24(17(2)21-6-7-22-19-13-28-40(55-28)27(43)9-8-26(42)39(40,5)23(19)10-11-38(21,22)4)52-35(49)20(16)15-50-36-33(48)31(46)34(25(14-41)53-36)54-37-32(47)30(45)29(44)18(3)51-37/h8-9,17-19,21-25,27-34,36-37,41,43-48H,6-7,10-15H2,1-5H3/t17-,18-,19-,21+,22-,23-,24+,25+,27-,28+,29-,30+,31+,32+,33+,34+,36+,37-,38+,39-,40+/m0/s1
SMILES (Click to copy)
O1[C@@H]2C[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)[C@@]5([H])CC(C)=C(CO[C@H]6[C@H](O)[C@@H](O)[C@H](O[C@H]7[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O7)[C@@H](CO)O6)C(=O)O5)[C@@]4(C)CC[C@]3([H])[C@]3(C(C=C[C@@H]([C@]132)O)=O)C

Other Databases

CHEBI ID
69112
PubChem CID
56649370

Calculated Physicochemical Properties

Heavy Atoms 55
Rings 8
Aromatic Rings
Rotatable Bonds 8
Van der Waals Molecular Volume 722.97
Topological Polar Surface Area 240.64
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 15
logP 4.61
Molar Refractivity 196.47

Admin

Created at
6th Dec 2023
Updated at
6th Dec 2023