(3S)-8-hydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

• ChemBase ID: 175759
• Molecular Formular: C19H14O4
• Molecular Mass: 306.31206
• Monoisotopic Mass: 306.08920893
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)ccc2c1C(=O)C[C@H](C2)C)O
• Canonical SMILES: C[C@@H]1CC(=O)c2c(C1)ccc1c2C(=O)c2c(C1=O)c(O)ccc2
• InChI: InChI=1S/C19H14O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-6,9,20H,7-8H2,1H3/t9-/m0/s1
• InChIKey: ZAWXOCUFQSQDJS-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-8-hydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione
• IUPAC Traditional name: (3S)-8-hydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione
• Synonyms: (S)-Ochromycinone, (+)-Ochromycinone, Deoxytetrangomycin, STA-21(3S)-3,4-Dihydro-8-hydroxy-3-methyl-Benz[a]anthracene-1,7,12(2H)-trione; Ochromycinone

Database IDs

• CAS Number: 28882-53-3
• PubChem SID: 164231669
• PubChem CID: 11808929

CALCULATED PROPERTIES

• Acid pKa: 9.023065
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.8599095
• LogD (pH = 7.4): 3.8498964
• Log P: 3.8600388
• Molar Refractivity: 85.9492 cm^3
• Polarizability: 32.439083 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Orange Solid
• Melting Point: 160-162°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - O150000

An angucycline antibiotic. A novel Stat3 selective inhibitor. It inhibits Stat3 dimerazation and DNA binding as well as Stat3-dependent luciferase reporter activity.

REFERENCES

• Song, H., et al.: Natl. Acad. Sci. USA, 102, 4700 (2005)