(2Z)-but-2-enedioic acid; 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one

• ChemBase ID: 163828
• Molecular Formular: C28H35N3O6S
• Molecular Mass: 541.659
• Monoisotopic Mass: 541.22465686
• SMILES: C(=C\C(=O)O)\C(=O)O.c1ccc2c(c1)N(c1c(S2)ccc(c1)C(=O)CC)CCCN1CCN(CC1)CCO
• Canonical SMILES: OC(=O)/C=C\C(=O)O.OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(=O)CC
• InChI: InChI=1S/C24H31N3O2S.C4H4O4/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28;5-3(6)1-2-4(7)8/h3-4,6-9,18,28H,2,5,10-17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: ZQYMISSXVDTVFZ-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
• IUPAC Traditional name: carphenazine; maleic acid
• Synonyms: 1-[10-[3-[4-(2-Hydroxyethyl)-1-piperazinyl]propyl]-10H-phenothiazin-2-yl]-1-propanone(2Z)-2-Butenedioate; Carfenazine Maleate; Carphenazin Maleate; Proketazine Maleate; Wy 2445; Carphenazine Dimaleate

Database IDs

• CAS Number: 2975-34-0
• PubChem SID: 162257963
• PubChem CID: 20838085

CALCULATED PROPERTIES

• Acid pKa: 15.556013
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.8263355
• LogD (pH = 7.4): 2.595799
• Log P: 3.3461566
• Molar Refractivity: 126.3236 cm^3
• Polarizability: 48.468433 Å^3
• Polar Surface Area: 47.02 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C184300

Antipsychotic.

REFERENCES

• Cooper, J., et al.: Br. J. Cancer, 39, 87 (1979)
• Forrest, S., et al.: Science, 261, 872 (1979)
• Contrera, J., et al.: Regul. Toxicol. Pharmacol., 38, 243 (1979)