Structure database (LMSD)

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LM IDLMST01070006
Common NameDioscoreside E
Systematic Name3-O-(Glcb1-3(Rhaa1-2)Glcb)-26-O-(Glcb)-23S-methoxy-(25R)-furosta-5,20(22)-dien-
3β,26-diol
Synonyms26-O-β-D-glucopyranosyl-3β,26-dihydroxy-23(S)-methoxy-25(R)-furosta-5,20(22)-
dien-3-O-α-L-rhamnopyranosyl(1-2)-[β-D-glucopyranosyl(1-3)]-β-D-
glucopyranoside
Exact Mass
1092.5716 (neutral)    Calculate m/z:
FormulaC53H88O23
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassFurostanols and derivatives [ST0107]
PubChem CID52931423
InChIKeyMBEWFQBRZYAFPE-YLHQKFOPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C53H88O23/c1-8-28-32(69-23(3)31(67-7)15-22(2)21-68-48-43(64)41(62)37(58
)33(18-54)72-48)17-30-27-10-9-25-16-26(11-13-52(25,5)29(27)12-14-53(28,30)6)71-5
1-47(76-49-44(65)40(61)36(57)24(4)70-49)46(39(60)35(20-56)74-51)75-50-45(66)42(6
3)38(59)34(19-55)73-50/h9,22,24,26-51,54-66H,3,8,10-21H2,1-2,4-7H3/t22-,24?,26+,
27-,28+,29+,30+,31+,32+,33?,34?,35?,36+,37-,38-,39-,40?,41+,42+,43?,44+,45?,46+,
47?,48-,49+,50+,51-,52+,53-/m1/s1
SMILES[C@]12(CC=C3C[C@@H](O[C@@H]4OC(CO)[C@@H](O)[C@H](O[C@@H]5OC(CO)[C@@H](O)[C@H](O)
C5O)C4O[C@@H]4OC(C)[C@H](O)C(O)[C@@H]4O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](CC
)[C@@H](OC(=C)[C@@H](OC)C[C@H](CO[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)C)C[C@@]21[H]
)[H]
StatusActive
ReferencesThe Dioscorea genus: a review of bioactive steroid saponins
Marc Sautour, Anne-Claire Mitaine-Offer and Marie-Aleth Lacaille-Dubois
J Nat Med (2007) 61:91-101
Calculated physicochemical properties (?):
 Heavy Atoms76Rings8Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
1023.47Topological Polar
Surface Area
363.57Hydrogen
Bond Donors
13Hydrogen
Bond Acceptors
23
 logP5.93Molar
Refractivity
275.41