carbenoxolone   

GtoPdb Ligand ID: 4151

Compound class: Synthetic organic
Comment: Carbenoxolone is derived from licorice root, and has a steroid-like chemical structure. Formulations used clinically typically contain carbenoxolone sodium.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 117.97
Molecular weight 570.36
XLogP 6.86
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(OC1CCC2(C(C1(C)C)CCC1(C2C(=O)C=C2C1(C)CCC1(C2CC(C)(CC1)C(=O)O)C)C)C)CCC(=O)O
Isomeric SMILES O=C(O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C)CCC(=O)O
InChI InChI=1S/C34H50O7/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40)/t21-,23-,24-,27+,30+,31-,32-,33+,34+/m0/s1
InChI Key OBZHEBDUNPOCJG-WBXJDKIVSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-(4-hydroxy-4-oxobutanoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
International Nonproprietary Names
INN number INN
1789 carbenoxolone
Database Links
CAS Registry No. 5697-56-3 (source: Scifinder)
ChEMBL Ligand CHEMBL499915
DrugCentral Ligand 493
GtoPdb PubChem SID 178100972
PubChem CID 636403
RCSB PDB Ligand CBO
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Wikipedia Carbenoxolone