Molecule ID: 16081995

IUPAC Name: (1S,4S,5R,8R,10S,13R,14R,17S,18R,19S,22S)-10,22-dihydroxy-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 hydroxy groups at position 3 and 22 (the 3beta,19alpha,22alpha 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 gamma-lactone, a bridged compound, a diol, a hexacyclic triterpenoid and a secondary alcohol. It derives from a hydride of a taraxastane.

SMILES: C=C1C[C@H](O)[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@H1][Branch1][C][O][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][S][C]

InChI: InChI=1S/C30H46O4/c1-17-16-22(32)29-15-14-28(7)27(6)12-8-19-25(3,4)21(31)10-11-26(19,5)20(27)9-13-30(28,34-24(29)33)23(29)18(17)2/h18-23,31-32H,1,8-16H2,2-7H3/t18-,19+,20-,21+,22+,23-,26+,27-,28+,29-,30+/m1/s1

Molecular Properties:
- Polar Surface Area: 66.8 Ų
- LogP: 5.7