(1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2-hydroperoxy-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 176393
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)C)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)OO
• Canonical SMILES: OO[C@]12CCC(=O)C=C1C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(O)C#C)C)C
• InChI: InChI=1S/C21H28O4/c1-4-20(23)9-7-16-18-13(2)11-14-12-15(22)5-10-21(14,25-24)17(18)6-8-19(16,20)3/h1,12-13,16-18,23-24H,5-11H2,2-3H3/t13-,16+,17+,18+,19+,20+,21-/m1/s1
• InChIKey: RURMXFRHKGLDHX-GWXLLEQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2-hydroperoxy-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2-hydroperoxy-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol; 1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine; Chloriprozine; Chlorperphenazine; Decentan; Emesinal; Etaperazin; Perfenil; Perphenan; Perphenazin; Sch 3940; Thilatazin; Tranquisan; Trifaron; Fluphenazine Imp. E (Pharmeuropa); Perphenazine

Database IDs

• CAS Number: 58-39-9
• PubChem SID: 164232303
• PubChem CID: 71751537

CALCULATED PROPERTIES

• Acid pKa: 11.69527
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.872236
• LogD (pH = 7.4): 2.8722146
• Log P: 2.8722365
• Molar Refractivity: 94.7744 cm^3
• Polarizability: 37.166264 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 95-98°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P291100

D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.

REFERENCES

• Gaertner, H.J., et al.: Drug Metab. Dispos., 3, 437 (1975)
• O Brien, S., et al.: J. Med. Chem., 48, 1287 (1975)
• Briggs, K., et al.: Toxicology, 231, 113 (1975)
• Toga, T., et al.: J. Pharmacol. Sci., 105, 207 (1975)