4-[(3,5-dihydroxyphenyl)methyl]-N-[(2-methyl-4-{4-methyl-2,4,5,9-tetraazatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),5,11,13-pentaene-9-carbonyl}phenyl)methyl]piperazine-1-carboxamide

• ChemBase ID: 179568
• Molecular Formular: C32H35N7O4
• Molecular Mass: 581.6648
• Monoisotopic Mass: 581.27505264
• SMILES: N1(Cc2c(Nc3c1cccc3)n(nc2)C)C(=O)c1cc(c(cc1)CNC(=O)N1CCN(CC1)Cc1cc(cc(c1)O)O)C
• Canonical SMILES: Oc1cc(CN2CCN(CC2)C(=O)NCc2ccc(cc2C)C(=O)N2Cc3cnn(c3Nc3c2cccc3)C)cc(c1)O
• InChI: InChI=1S/C32H35N7O4/c1-21-13-23(31(42)39-20-25-18-34-36(2)30(25)35-28-5-3-4-6-29(28)39)7-8-24(21)17-33-32(43)38-11-9-37(10-12-38)19-22-14-26(40)16-27(41)15-22/h3-8,13-16,18,35,40-41H,9-12,17,19-20H2,1-2H3,(H,33,43)
• InChIKey: HWPGRFRXZNLZEX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3,5-dihydroxyphenyl)methyl]-N-[(2-methyl-4-{4-methyl-2,4,5,9-tetraazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),5,11,13-pentaene-9-carbonyl}phenyl)methyl]piperazine-1-carboxamide
• IUPAC Traditional name: 4-[(3,5-dihydroxyphenyl)methyl]-N-[(2-methyl-4-{4-methyl-2,4,5,9-tetraazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),5,11,13-pentaene-9-carbonyl}phenyl)methyl]piperazine-1-carboxamide
• Synonyms: N-[[4-[(4,10-Dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-4-[(3,5-dihydroxyphenyl)methyl]-1-piperazinecarboxamide Dihydrochloride; WAY 267464 Dihydrochloride

Database IDs

• CAS Number: 847375-16-0
• PubChem SID: 164235478
• PubChem CID: 9938214

CALCULATED PROPERTIES

• Acid pKa: 9.145431
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.7008073
• LogD (pH = 7.4): 3.1554105
• Log P: 3.173806
• Molar Refractivity: 175.9579 cm^3
• Polarizability: 61.944645 Å^3
• Polar Surface Area: 126.2 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - W498600

WAY 267464 is a potent, selective non-peptide oxytocin receptor (OTR) agonist (Ki = 58.4 nM at human OTR). WAY 267464 exhibits anxiolytic-like effects. May have therapeutic potential for the treatment of psychosis and schizophrenia.

REFERENCES

• Burbach, J., et al.: J. Biol. Chem., 258, 1487 (1983)
• Amico, J., et al.: Pharmacol. Biochem. Behav., 78, 333 (1983)
• Ashworth, D., et al.: Drugs Future, 31, 345 (1983)
• Ring, et al.: Neuropharmacology, 58, 6 (1983)