Molecule ID: 11061975

IUPAC Name: (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol

Description: The molecule is a triterpenoid saponin that consists of urs-11-ene substituted by an epoxy group across positions 13 and 28, a hydroxy group at position 16 and a beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyloxy group at position 3 (the 3beta,16alpha stereoisomer). Isolated from the fruits of Bupleurum rotundifolium, it exhibits antiproliferative activity against cancer cells. It has a role as an antineoplastic agent and a plant metabolite. It is a triterpenoid saponin, a hexacyclic triterpenoid, a trisaccharide derivative, a cyclic ether and a bridged compound. It derives from a hydride of an ursane.

SMILES: C[C@H]1[C@H](C)CC[C@]23CO[C@@]4(C=C[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]2O)[C@H]13

SELFIES: [C][C@H1][C@H1][Branch1][C][C][C][C][C@][C][O][C@@][Branch2][Branch2][Branch1][C][=C][C@@H1][C@@][Branch1][C][C][C][C][C@H1][Branch2][Branch1][#Branch1][O][C@@H1][O][C@H1][Branch1][Ring1][C][O][C@@H1][Branch1][C][O][C@H1][Branch1][C][O][C@H1][Ring1][#Branch2][O][C@@H1][O][C@H1][Branch1][Ring1][C][O][C@@H1][Branch1][C][O][C@H1][Branch1][C][O][C@H1][Ring1][#Branch2][O][C@@H1][O][C][C@@H1][Branch1][C][O][C@H1][Branch1][C][O][C@H1][Ring1][Branch2][O][C][Branch1][C][C][Branch1][C][C][C@@H1][Ring2][Ring2][=Branch2][C][C][C@@][Ring2][Ring2][=N][Branch1][C][C][C@][Ring2][Branch1][C][Branch1][C][C][C][C@H1][Ring2][Branch1][Branch2][O][C@H1][Ring2][Branch1][#C][Ring2][Branch1][#Branch2]

InChI: InChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-43(5)12-11-29(42(3,4)26(43)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)31(53)24(17-48)60-40)64-41-37(34(56)32(54)25(18-49)61-41)63-39-35(57)30(52)23(50)19-58-39/h10,15,21-41,48-57H,8-9,11-14,16-20H2,1-7H3/t21-,22+,23-,24-,25-,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,43+,44-,45+,46+,47+/m1/s1

Molecular Properties:
- Polar Surface Area: 267.0 Ų
- LogP: 1.8