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
1076.5403 (neutral)    Calculate m/z:
FormulaC52H84O23
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassFurostanols and derivatives [ST0107]
PubChem CID52931423
InChIKeyWSWNKHNNDHPGMZ-ZMCISRQXSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C52H84O23/c1-20(19-67-47-41(63)39(61)35(57)30(16-53)71-47)13-29(66-6)44-21(2)33-28(70-44)15-27-25-8-7-23-14-24(9-11-51(23,4)26(25)10-12-52(27,33)5)69-50-46(75-48-42(64)38(60)34(56)22(3)68-48)45(37(59)32(18-55)73-50)74-49-43(65)40(62)36(58)31(17-54)72-49/h7,20,22,24-43,45-50,53-65H,8-19H2,1-6H3/t20-,22?,24+,25-,26+,27+,28+,29+,30?,31?,32?,33+,34+,35-,36-,37-,38?,39+,40+,41?,42+,43?,45+,46?,47-,48+,49+,50-,51+,52+/m1/s1
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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]3C(=C([C@@H](OC)C[C@H](CO[C@@H]4OC(CO)[C@@H](O)[C@H](O)C4O)C)O[C@H]3C[C@@]21[H])C)[H]
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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