Structure database (LMSD)

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LM IDLMST01070010
Common NameDioscoreside C
Systematic Name3-O-(Rhaa1-4(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-23S-methoxy-25(R)-furosta-5,20(22)-
dien-3-O-α-L-rhamnopyranosyl(1-2)-[α-L-rhamnopyranosyl(1-4)]-β-D-
glucopyranoside
Exact Mass
1060.5454 (neutral)    Calculate m/z:
FormulaC52H84O22
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassFurostanols and derivatives [ST0107]
PubChem CID52931427
InChIKeyGOKDEZKNKCIMJT-GYUHQQEOSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C52H84O22/c1-20(19-66-47-40(61)39(60)36(57)31(17-53)71-47)14-30(65-7)44-21(2)33-29(70-44)16-28-26-9-8-24-15-25(10-12-51(24,5)27(26)11-13-52(28,33)6)69-50-46(74-49-42(63)38(59)35(56)23(4)68-49)43(64)45(32(18-54)72-50)73-48-41(62)37(58)34(55)22(3)67-48/h8,20,22-23,25-43,45-50,53-64H,9-19H2,1-7H3/t20-,22?,23?,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]5OC(C)[C@H](O)C(O)[C@H]5O)[C@H](O)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 Atoms75Rings8Aromatic Rings0Rotatable Bonds18
 van der Waals
Molecular Volume
1014.68Topological Polar
Surface Area
343.34Hydrogen
Bond Donors
12Hydrogen
Bond Acceptors
22
 logP6.67Molar
Refractivity
273.51