ARL 67156   Click here for help

GtoPdb Ligand ID: 9030

Synonyms: 6-N,N-diethyl-beta,gamma-dibromomethylene-D-ATP | ARL-67156 | FPL 67156 | FPL-67156
PDB Ligand
Compound class: Synthetic organic
Comment: ARL 67156 is a research compound used experimantally as the trisodium salt PubChem CID 11957464). It is an inhibitor of ecto-ATPase activity. Structurally, ARL 67156 is an analogue of ATP and therefore competes with substrate at the enzyme.
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 16
Hydrogen bond donors 6
Rotatable bonds 11
Topological polar surface area 276.55
Molecular weight 716.9
XLogP -1.91
No. Lipinski's rules broken 3
Click here for help
Canonical SMILES CCN(c1ncnc2c1ncn2C1OC(C(C1O)O)COP(=O)(OP(=O)(C(P(=O)(O)O)(Br)Br)O)O)CC
Isomeric SMILES CCN(c1ncnc2c1ncn2[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(OP(=O)(C(P(=O)(O)O)(Br)Br)O)O)CC
InChI InChI=1S/C15H24Br2N5O12P3/c1-3-21(4-2)12-9-13(19-6-18-12)22(7-20-9)14-11(24)10(23)8(33-14)5-32-37(30,31)34-36(28,29)15(16,17)35(25,26)27/h6-8,10-11,14,23-24H,3-5H2,1-2H3,(H,28,29)(H,30,31)(H2,25,26,27)/t8-,10-,11-,14-/m1/s1
1. Brunschweiger A, Iqbal J, Umbach F, Scheiff AB, Munkonda MN, Sévigny J, Knowles AF, Müller CE. (2008)
Selective nucleoside triphosphate diphosphohydrolase-2 (NTPDase2) inhibitors: nucleotide mimetics derived from uridine-5'-carboxamide.
J Med Chem, 51 (15): 4518-28. [PMID:18630897]
2. Crack BE, Pollard CE, Beukers MW, Roberts SM, Hunt SF, Ingall AH, McKechnie KC, IJzerman AP, Leff P. (1995)
Pharmacological and biochemical analysis of FPL 67156, a novel, selective inhibitor of ecto-ATPase.
Br J Pharmacol, 114 (2): 475-81. [PMID:7533620]