19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

• ChemBase ID: 105312
• Molecular Formular: C20H16N2O4
• Molecular Mass: 348.35204
• Monoisotopic Mass: 348.111007
• SMILES: CCC1(O)C(=O)OCc2c1cc1n(Cc3cc4c(cccc4)nc13)c2=O
• Canonical SMILES: CCC1(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
• InChIKey: VSJKWCGYPAHWDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• IUPAC Traditional name: @camptothecin
• Synonyms: Camptothecine; CAMPTOTHECIN

Database IDs

• CAS Number: 7689-03-4
• PubChem SID: 162092319
• PubChem CID: 2538

CALCULATED PROPERTIES

• Acid pKa: 11.710533
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.2186455
• LogD (pH = 7.4): 1.2202018
• 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

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: UQ0492000

Product Information

• Purity: 97%

DETAILS

MP Biomedicals - 02159732

Purity: 97%
Binds to and stabilizes the topoisomerase-DNA covalent complex which reversibly inhibits nuclear topoisomerase I. Also inhibits TAT-mediated HIV-1 transactivation.

REFERENCES

• Hertzberg, R.P., et al., Biochem. J. , 28 : 4629, (1990)
• Hsiang, Y.H., et al., J. Biol. Chem. , 260 : 14873, (1985)
• Li, C.J., et al., J. Biol. Chem. , 269 : 7051, (1994).