Structure database (LMSD)

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LM IDLMST01070014
Common NameMethyl protogracillin
Systematic Name3-O-(Glcb1-4(Rhaa1-2)Glcb)-26-O-(Glcb)-22-methoxy-(25R)-furost-5-ene-3β,26-
diol
Synonyms3-O-(β-D-glucopyranosyl-(1-4)-(α-L-rhamnopyranosyl-(1-2))-β-D-
glucopyranosyl)-26-O-(β-D-glucopyranosyl)-22-methoxy-(25R)-furost-5-ene-3β,
26-diol
Exact Mass
1078.5924 (neutral)    Calculate m/z:
FormulaC53H90O22
CategorySterol Lipids [ST]
Main ClassSterols [ST01]
Sub ClassFurostanols and derivatives [ST0107]
PubChem CID70699388
InChIKeyZFYYMSQQUPRMFY-IZUUDHNCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C53H90O22/c1-8-29-33(75-53(6,66-7)16-11-24(2)23-67-48-44(64)43(63)40(60
)35(21-55)71-48)18-31-28-10-9-26-17-27(12-14-51(26,4)30(28)13-15-52(29,31)5)69-5
0-47(74-49-45(65)42(62)38(58)25(3)68-49)46(41(61)36(22-56)72-50)73-37-19-32(57)3
9(59)34(20-54)70-37/h9,24-25,27-50,54-65H,8,10-23H2,1-7H3/t24-,25?,27+,28-,29+,3
0+,31+,32-,33+,34?,35?,36?,37+,38+,39+,40-,41-,42?,43+,44?,45+,46+,47?,48-,49+,5
0-,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)
C5)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](O[C@@](OC)(C)CC[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 Atoms75Rings8Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
1017.32Topological Polar
Surface Area
343.34Hydrogen
Bond Donors
12Hydrogen
Bond Acceptors
22
 logP6.90Molar
Refractivity
273.60