2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 160885
• Molecular Formular: C22H19ClO3
• Molecular Mass: 366.83746
• Monoisotopic Mass: 366.10227215
• SMILES: c12c(C(=O)C(=C(C1=O)C1CC[C@@H](CC1)c1ccc(cc1)Cl)O)cccc2
• Canonical SMILES: Clc1ccc(cc1)[C@@H]1CCC(CC1)C1=C(O)C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15?
• InChIKey: KUCQYCKVKVOKAY-AZZIRIGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: wellvone
• Synonyms: 2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione; 566C80; BW-566C; BW-566C-80; Mepron; Wellvone; Atovaquone

Database IDs

• CAS Number: 95233-18-4
• PubChem SID: 162255020
• PubChem CID: 74989

CALCULATED PROPERTIES

• Acid pKa: 8.233868
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.9968457
• LogD (pH = 7.4): 4.9382534
• Log P: 4.9976463
• Molar Refractivity: 103.1065 cm^3
• Polarizability: 39.141586 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Yellow to Orange Solid
• Melting Point: 216-219°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A793500

Hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport. Antipneumocystic.

REFERENCES

• Hudson, A.T., et al.: Drugs Exp. Clin. Res., 17, 427 (1991)
• Fry, M., et al.: Biochem. Pharmacol., 43, 1545 (1991)
• El-Sadr, W.M., et al.: N. Engl. J. Med., 339, 1889 (1991)