isothiourea-1t   Click here for help

GtoPdb Ligand ID: 2899

Synonyms: IT1t
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Potent CXCR4 antagonist.

Available experimental ADMET data:
Cytochrome P450 inhibition CYP1A2, CYP2C9, CYP3A4 (less than 5); CYP2C19 (5.3);CYP2D6 (6.4)
hERG pIC50 cellular (less than 4.7), binding (4.9)
hERG pIC50 cellular (less than 4.7), binding (4.9)
pKa 9.6, 8.0
LogP, LogD 4.5, 1.2
solubility (pH 1.0,pH 6.8 )g/L >5, >5
see [2] for more details
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 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 95.22
Molecular weight 406.22
XLogP 5.63
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CC1(C)N=c2n(C1)c(cs2)CSC(=NC1CCCCC1)NC1CCCCC1
Isomeric SMILES CC1(C)N=c2n(C1)c(cs2)CS/C(=N\C1CCCCC1)/NC1CCCCC1
InChI InChI=1S/C21H34N4S2/c1-21(2)15-25-18(14-27-20(25)24-21)13-26-19(22-16-9-5-3-6-10-16)23-17-11-7-4-8-12-17/h14,16-17H,3-13,15H2,1-2H3,(H,22,23)
1. Adlere I, Sun S, Zarca A, Roumen L, Gozelle M, Viciano CP, Caspar B, Arimont M, Bebelman JP, Briddon SJ et al.. (2019)
Structure-based exploration and pharmacological evaluation of N-substituted piperidin-4-yl-methanamine CXCR4 chemokine receptor antagonists.
Eur J Med Chem, 162: 631-649. DOI: 10.1016/j.ejmech.2018.10.060 [PMID:30476826]
2. Thoma G, Streiff MB, Kovarik J, Glickman F, Wagner T, Beerli C, Zerwes HG. (2008)
Orally bioavailable isothioureas block function of the chemokine receptor CXCR4 in vitro and in vivo.
J Med Chem, 51 (24): 7915-20. [PMID:19053768]