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

• ChemBase ID: 177650
• Molecular Formular: C20H16O4
• Molecular Mass: 320.33864
• Monoisotopic Mass: 320.10485899
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)ccc2c1C(=O)C[C@H](C2)C)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1ccc3c(c1C2=O)C(=O)C[C@H](C3)C
• InChI: InChI=1S/C20H16O4/c1-10-8-11-6-7-13-18(16(11)14(21)9-10)20(23)12-4-3-5-15(24-2)17(12)19(13)22/h3-7,10H,8-9H2,1-2H3/t10-/m0/s1
• InChIKey: ZUCWNLVDTXGGSU-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-8-methoxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione
• IUPAC Traditional name: (3S)-8-methoxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione
• Synonyms: (4S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3’,4’:6,7]indolizinol[1,2-b]quinoline-3,14(4H,-12H)-dione; 9-Nitrocamptothecin; 9-NC; Orathecin; Rubitecan

Database IDs

• CAS Number: 91421-42-0
• PubChem SID: 164233560
• PubChem CID: 10958178

CALCULATED PROPERTIES

• Acid pKa: 16.519781
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.3559327
• LogD (pH = 7.4): 3.3559327
• Log P: 3.3559327
• Molar Refractivity: 90.4315 cm^3
• Polarizability: 34.35066 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >255°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R701500

Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic.

REFERENCES

• Stehlin, J.S., et al.: Int. J. Oncol., 14, 821 (1999)
• Verschraegen, C.F., et al.: Curr. Opin. Oncol. Endocr. Metab. Invest. Drugs, 1, 184 (1999)