(2Z)-but-2-enedioic acid; 1-[10-(3-{4-[2-hydroxy(2H4)ethyl]piperazin-1-yl}propyl)-10H-phenothiazin-2-yl]ethan-1-one

• ChemBase ID: 158971
• Molecular Formular: C27H33N3O6S
• Molecular Mass: 527.63242
• Monoisotopic Mass: 527.20900679
• SMILES: C(=C\C(=O)O)\C(=O)O.c1ccc2c(c1)N(c1c(S2)ccc(c1)C(=O)C)CCCN1CCN(CC1)CCO
• Canonical SMILES: OC(=O)/C=C\C(=O)O.OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(=O)C
• InChI: InChI=1S/C23H29N3O2S.C4H4O4/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27;5-3(6)1-2-4(7)8/h2-3,5-8,17,27H,4,9-16H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: JVMBOHDUHCHGOE-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 1-[10-(3-{4-[2-hydroxy(^2H₄)ethyl]piperazin-1-yl}propyl)-10H-phenothiazin-2-yl]ethan-1-one
• IUPAC Traditional name: 1-[10-(3-{4-[2-hydroxy(^2H₄)ethyl]piperazin-1-yl}propyl)phenothiazin-2-yl]ethanone; maleic acid
• Synonyms: 1-[10-[3-[4-(2-Hydroxyethyl-d4)-1-piperazinyl]propyl]-10H-phenothiazin-2-yl]ethanone (2Z)-2-Butenedioate; Acetophenazine-d4 Maleate; NSC 169180-d4; NSC 70600-d4; Phentoxate-d4; Sch 6673-d4; Tindal-d4; Tindala-d4; Acetophenazine-d4 Dimaleate

Database IDs

• PubChem SID: 162253106
• PubChem CID: 71312760

CALCULATED PROPERTIES

• Acid pKa: 15.464547
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.12574665
• LogD (pH = 7.4): 1.8952147
• Log P: 2.6456206
• Molar Refractivity: 121.6967 cm^3
• Polarizability: 46.62468 Å^3
• Polar Surface Area: 47.02 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A163932

Labelled Acetophenazine (A163930). Antipsychotic.

REFERENCES

• Schafer, E.W., et al.: Toxicol. Appl. Pharmacol., 21, 315 (1972)