S(+)-niguldipine   Click here for help

GtoPdb Ligand ID: 487

Synonyms: (+)-niguldipine
Compound class: Synthetic organic
Comment: The following stereoisomers and enantiomers of niguldipine exist: R(-)-niguldipine (dexniguldipine, INN), and S(+)-niguldipine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 111.01
Molecular weight 609.28
XLogP 7.67
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCCCN1CCC(CC1)(c1ccccc1)c1ccccc1)C
Isomeric SMILES COC(=O)C1=C(C)NC(=C([C@H]1c1cccc(c1)[N+](=O)[O-])C(=O)OCCCN1CCC(CC1)(c1ccccc1)c1ccccc1)C
InChI InChI=1S/C36H39N3O6/c1-25-31(34(40)44-3)33(27-12-10-17-30(24-27)39(42)43)32(26(2)37-25)35(41)45-23-11-20-38-21-18-36(19-22-38,28-13-6-4-7-14-28)29-15-8-5-9-16-29/h4-10,12-17,24,33,37H,11,18-23H2,1-3H3/t33-/m0/s1
InChI Key SVJMLYUFVDMUHP-XIFFEERXSA-N
References
1. Ford AP, Daniels DV, Chang DJ, Gever JR, Jasper JR, Lesnick JD, Clarke DE. (1997)
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.
Br J Pharmacol, 121 (6): 1127-35. [PMID:9249248]
2. Shibata K, Foglar R, Horie K, Obika K, Sakamoto A, Ogawa S, Tsujimoto G. (1995)
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.
Mol Pharmacol, 48 (2): 250-8. [PMID:7651358]
3. Waugh DJ, Gaivin RJ, Zuscik MJ, Gonzalez-Cabrera P, Ross SA, Yun J, Perez DM. (2001)
Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists.
J Biol Chem, 276 (27): 25366-71. [PMID:11331292]