(2Z)-but-2-enedioic acid; 10-[2-methyl-3-(methylamino)propyl]-10H-phenothiazine-2-carbonitrile

• ChemBase ID: 165751
• Molecular Formular: C22H23N3O4S
• Molecular Mass: 425.50072
• Monoisotopic Mass: 425.14092723
• SMILES: C(=C\C(=O)O)\C(=O)O.c1ccc2c(c1)N(c1c(S2)ccc(c1)C#N)CC(CNC)C
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CNCC(CN1c2ccccc2Sc2c1cc(C#N)cc2)C
• InChI: InChI=1S/C18H19N3S.C4H4O4/c1-13(11-20-2)12-21-15-5-3-4-6-17(15)22-18-8-7-14(10-19)9-16(18)21;5-3(6)1-2-4(7)8/h3-9,13,20H,11-12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: JPDYIRZKEDRQOF-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 10-[2-methyl-3-(methylamino)propyl]-10H-phenothiazine-2-carbonitrile
• IUPAC Traditional name: 10-[2-methyl-3-(methylamino)propyl]phenothiazine-2-carbonitrile; maleic acid
• Synonyms: 10-[2-Methyl-3-(methylamino)propyl]-10H-phenothiazine-2-carbonitrile Maleate; 10-(2-Methyl-3-methylaminopropyl)phenothiazine-2-carbonitrile Maleate; N-Demethylcyamemazine Maleate

Database IDs

• PubChem SID: 162259884
• PubChem CID: 71315374

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.65805095
• LogD (pH = 7.4): 1.2558862
• Log P: 3.8833275
• Molar Refractivity: 93.7948 cm^3
• Polarizability: 35.95814 Å^3
• Polar Surface Area: 39.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230895

Cyamemazine (C951500) metabolite.

REFERENCES

• Crumb, W., et al.: J. Pharm. Pharmacol., 60, 1507 (2008)
• Benyamina, A., et al.: Eur. J. Pharmacol., 578, 142 (2008)