(19R)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

• ChemBase ID: 163569
• Molecular Formular: C20H16N2O4
• Molecular Mass: 348.35204
• Monoisotopic Mass: 348.111007
• SMILES: c1ccc2c(c1)cc1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(O)CC
• Canonical SMILES: CC[C@]1(O)C(=O)OCc2c1cc1c3nc4ccccc4cc3Cn1c2=O
• InChI: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m1/s1
• InChIKey: VSJKWCGYPAHWDS-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19R)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• IUPAC Traditional name: (19R)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• Synonyms: (R)-4-Ethyl-4-hydroxy-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; (R)-(-)-Camptothecine; (R)-Camptothecin; 20R-Camptothecin; (R)-(-)-Camptothecin

Database IDs

• CAS Number: 110351-92-3
• PubChem SID: 162257704
• PubChem CID: 184196

CALCULATED PROPERTIES

• Acid pKa: 11.708908
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.2186455
• LogD (pH = 7.4): 1.2202017
• Log P: 1.2202432
• Molar Refractivity: 94.4925 cm^3
• Polarizability: 37.18863 Å^3
• Polar Surface Area: 79.73 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C175145

Antitumor alkaloid. Binds irreversible to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. A cytotoxic antitumor agent.

REFERENCES

• Potmesil, M., et al.: Cancer Res., 54, 1431 (1994)
• Desai, S.D., et al.: J. Biol. Chem., 272, 24159 (1994)
• Fan, Y., et al.: J. Med. Chem., 41, 2216 (1994)
• Kaufmann, S.H., et al.: Biochim. Biophys. Acta, 1400, 195 (1994)