VUF14738   Click here for help

GtoPdb Ligand ID: 9873

Synonyms: compound 28 [PMID: 29470065] | VUF 14738 | VUF-14738
Compound class: Synthetic organic
Comment: VUF14738 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. VUF14738 binding is 'switched-on' by UV light. VUF14738 swiftly and reversibly photoisomerizes (via trans/cis conversion) and is suitable for spatiotemporal studies of H3 receptor signaling. See also VUF14862, 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 9
Topological polar surface area 57.5
Molecular weight 420.25
XLogP 5.18
No. Lipinski's rules broken 1
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Canonical SMILES O=C(c1cccc(c1)N=Nc1cccc(c1)OCCCN1CCCCC1)N1CCCC1
Isomeric SMILES O=C(c1cccc(c1)/N=N\c1cccc(c1)OCCCN1CCCCC1)N1CCCC1
InChI InChI=1S/C25H32N4O2/c30-25(29-16-4-5-17-29)21-9-6-10-22(19-21)26-27-23-11-7-12-24(20-23)31-18-8-15-28-13-2-1-3-14-28/h6-7,9-12,19-20H,1-5,8,13-18H2/b27-26-
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Molecular structure representations generated using Open Babel