VUF14862   Click here for help

GtoPdb Ligand ID: 9874

Synonyms: compound 33 [PMID: 29470065] | VUF 14862 | VUF-14862
Compound class: Synthetic organic
Comment: VUF14862 is a bidirectional photo-switchable histamine H3 receptor antagonist based on the structure of compound 3a [PMID: 18606542] [1]. The chemical structure shown here is the photo-activated isomer that binds the H3 receptor under UV illumination. VUF14862 binding is 'switched-off' by UV light. VUF14862 swiftly and reversibly photoisomerizes (via trans/cis conversion) and is suitable for spatiotemporal studies of H3 receptor signaling. See also VUF14738, which operates in the opposite direction.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 57.5
Molecular weight 432.25
XLogP 5.41
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C(c1cccc(c1)N=Nc1cccc(c1)OC1CC(C1)N1CCCCC1)N1CCCC1
Isomeric SMILES O=C(c1cccc(c1)/N=N/c1cccc(c1)OC1C[C@H](C1)N1CCCCC1)N1CCCC1
InChI InChI=1S/C26H32N4O2/c31-26(30-14-4-5-15-30)20-8-6-9-21(16-20)27-28-22-10-7-11-24(17-22)32-25-18-23(19-25)29-12-2-1-3-13-29/h6-11,16-17,23,25H,1-5,12-15,18-19H2/b28-27+/t23-,25?
InChI Key QQXICCNAEXQIHK-JMBHWGOTSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-(3-{3-[(E)-2-[3-(pyrrolidine-1-carbonyl)phenyl]diazen-1-yl]phenoxy}cyclobutyl)piperidine
Synonyms Click here for help
compound 33 [PMID: 29470065] | VUF 14862 | VUF-14862
Database Links Click here for help
GtoPdb PubChem SID 363894168
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