(10S)-10-(methylamino)-1,3-diazatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-2-one; (2Z)-but-2-enedioic acid

• ChemBase ID: 178029
• Molecular Formular: C15H17N3O5
• Molecular Mass: 319.31258
• Monoisotopic Mass: 319.11682066
• SMILES: c1cc2c3c(c1)C[C@@H](Cn3c(=O)[nH]2)NC.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CN[C@H]1Cc2cccc3c2n(C1)c(=O)[nH]3
• InChI: InChI=1S/C11H13N3O.C4H4O4/c1-12-8-5-7-3-2-4-9-10(7)14(6-8)11(15)13-9;5-3(6)1-2-4(7)8/h2-4,8,12H,5-6H2,1H3,(H,13,15);1-2H,(H,5,6)(H,7,8)/b;2-1-/t8-;/m0./s1
• InChIKey: VOJRMYBBPKNLLI-KZDSSNOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-(methylamino)-1,3-diazatricyclo[6.3.1.0^4,^1^2]dodeca-4,6,8(12)-trien-2-one; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: (10S)-10-(methylamino)-1,3-diazatricyclo[6.3.1.0^4,^1^2]dodeca-4,6,8(12)-trien-2-one; maleic acid
• Synonyms: (5R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (2Z)-2-Butenedioate; (R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (2Z)-2-Butenedioate; Sumanirole Maleate

Database IDs

• CAS Number: 179386-43-7
• PubChem SID: 164233939
• PubChem CID: 71752303

CALCULATED PROPERTIES

• Acid pKa: 12.884821
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.1628203
• LogD (pH = 7.4): -0.7841525
• Log P: 0.9256609
• Molar Refractivity: 58.8149 cm^3
• Polarizability: 21.919672 Å^3
• Polar Surface Area: 44.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S790700

Sumanirole is a high affinity D2 receptor agonist (EC50 values are between 17 and 75 nM in cell-based assays). Sumanirole displays >200-fold selectivity for the D2 receptor against other dopamine receptor subtypes (Ki values are 9.0, 1940, >2190 and >7140

REFERENCES

• McCall, et al.: J. Pharmacol. Exp. Ther., 314 1248 (2005)
• Stephenson, et al.: J. Pharmacol. Exp. Ther., 314 1257 (2005)