(1R,3S)-1,7,9-trihydroxy-3-methyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

• ChemBase ID: 178614
• Molecular Formular: C14H12O6
• Molecular Mass: 276.24148
• Monoisotopic Mass: 276.0633881
• SMILES: c1c(cc2c(c1O)C(=O)C1=C(C2=O)C[C@@H](O[C@H]1O)C)O
• Canonical SMILES: C[C@@H]1O[C@@H](O)C2=C(C1)C(=O)c1c(C2=O)c(O)cc(c1)O
• InChI: InChI=1S/C14H12O6/c1-5-2-7-11(14(19)20-5)13(18)10-8(12(7)17)3-6(15)4-9(10)16/h3-5,14-16,19H,2H2,1H3/t5-,14+/m0/s1
• InChIKey: NNXPHSFVRRTOJM-OVZGEXIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-1,7,9-trihydroxy-3-methyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione
• IUPAC Traditional name: thysanone
• Synonyms: (1R,3S)-3,4-Dihydro-1,7,9-trihydroxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione; (-)-Thysanone

Database IDs

• CAS Number: 233279-24-8
• PubChem SID: 164234524
• PubChem CID: 10333648

CALCULATED PROPERTIES

• Acid pKa: 7.3914633
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.2639627
• LogD (pH = 7.4): 0.966958
• Log P: 1.2694619
• Molar Refractivity: 69.1022 cm^3
• Polarizability: 26.105068 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T426500

A fungal benzoisochromanquinone with potent human rhinovirus 3C-protease inhibitory activity.

REFERENCES

• Patterson, E., et al.: Experientia, 22, 209 (1966)
• Singh, S., et al.: Bioorg. Med. Chem. Lett., 11, 3143 (1966)
• Movassaghi, M., et al.: Science, 298, 1904 (1966)