Molecule ID: 16081994

IUPAC Name: (1S,4S,5R,8R,10S,13R,14R,17S,18R,19S)-10-hydroxy-4,5,9,9,13,19-hexamethyl-20-methylidene-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one

Description: The molecule is a hexacyclic triterpenoid that is 13,28-epoxyursan-28-one with a terminal double bond between positions 20(30) and is substituted by a hydroxy group at position 3 (the 3beta,19alpha stereoisomer). It is a taraxastane-type triterpene isolated from Hypericum oblongifolium and exhibits enzyme inhibitory activity against chymotrypsin. It has a role as a metabolite and an EC 3.4.21.1 (chymotrypsin) inhibitor. It is a hexacyclic triterpenoid, a gamma-lactone, a bridged compound and a secondary alcohol. It derives from a hydride of a taraxastane.

SMILES: C=C1CC[C@@]23CC[C@]4(C)[C@@](CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@@H]6CC[C@]54C)(OC2=O)[C@@H]3[C@@H]1C

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

InChI: InChI=1S/C30H46O3/c1-18-8-14-29-17-16-28(7)27(6)13-9-20-25(3,4)22(31)11-12-26(20,5)21(27)10-15-30(28,33-24(29)32)23(29)19(18)2/h19-23,31H,1,8-17H2,2-7H3/t19-,20+,21-,22+,23-,26+,27-,28+,29+,30+/m1/s1

Molecular Properties:
- Polar Surface Area: 46.5 Ų
- LogP: 6.6