compound 11d [PMID: 34406006]   Click here for help

GtoPdb Ligand ID: 11697

Compound class: Synthetic organic
Comment: Compound 11d is a betulinic acid-derived G protein-coupled bile acid receptor 1 (GPBAR1, a.k.a. TGR5) agonist [1]. It was used experimentally as 11d-sodium to increase its solubility. 11d is inactive at FXR, which indicates good selectivity toward GPBAR1. In vivo, 11d produced very limited glucose-lowering effects (determined using the oral glucose tolerance test) in wild-type mice, but did induce the desired glucose-lowering effect in mice expressing a receptor with a humanising amino acid substitution (mTGR5H88Y).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 95.86
Molecular weight 543.39
XLogP 8.76
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(O[C@@H]1CC[C@]2(C(C1(C)C)CC[C@@]1(C2CCC2[C@@]1(C)CC[C@@]1(C2[C@@H](CC1)[C@@H](O)C)C(=O)O)C)C)NC1CC1
Isomeric SMILES CC1(C)[C@H](OC(=O)NC2CC2)CC[C@@]2(C)C1CC[C@]1(C)C2CCC2[C@@]1(C)CC[C@]1(C(=O)O)C2[C@H]([C@H](C)O)CC1
InChI InChI=1S/C33H53NO5/c1-19(35)21-11-16-33(27(36)37)18-17-31(5)22(26(21)33)9-10-24-30(4)14-13-25(39-28(38)34-20-7-8-20)29(2,3)23(30)12-15-32(24,31)6/h19-26,35H,7-18H2,1-6H3,(H,34,38)(H,36,37)/t19-,21-,22?,23?,24?,25+,26?,30-,31+,32+,33-/m0/s1
InChI Key NZSQBRZWARZNQH-ZWOACCQCSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1R,3aS,5aR,5bR,9R,11aR)-9-((Cyclopropylcarbamoyl)oxy)-1-((S)-1-hydroxyethyl)-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate
Database Links Click here for help
Specialist databases
GPCRdb Ligand compound 11d [PMID: 34406006]
Other databases
GtoPdb PubChem SID 442878723
Search Google for chemical match using the InChIKey NZSQBRZWARZNQH-ZWOACCQCSA-N
Search Google for chemicals with the same backbone NZSQBRZWARZNQH
UniChem Compound Search for chemical match using the InChIKey NZSQBRZWARZNQH-ZWOACCQCSA-N
UniChem Connectivity Search for chemical match using the InChIKey NZSQBRZWARZNQH-ZWOACCQCSA-N