(19S)-19-ethyl-19-hydroxy-10-methyl-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: 173471
• Molecular Formular: C21H18N2O4
• Molecular Mass: 362.37862
• Monoisotopic Mass: 362.12665707
• SMILES: c1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)C
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccccc4c(c3Cn1c2=O)C
• InChI: InChI=1S/C21H18N2O4/c1-3-21(26)15-8-17-18-13(11(2)12-6-4-5-7-16(12)22-18)9-23(17)19(24)14(15)10-27-20(21)25/h4-8,26H,3,9-10H2,1-2H3/t21-/m0/s1
• InChIKey: XRCMSKXVQYEFOZ-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-19-ethyl-19-hydroxy-10-methyl-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: (19S)-19-ethyl-19-hydroxy-10-methyl-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: (4S)-4-Ethyl-4-hydroxy-11-methyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione; 7-Methyl-20(S)-camptothecin; 7-Methylcamptothecin; 7-Methyl Camptothecin

Database IDs

• CAS Number: 78287-26-0
• PubChem SID: 164229381
• PubChem CID: 9799066

CALCULATED PROPERTIES

• Acid pKa: 11.709059
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.7216853
• LogD (pH = 7.4): 1.7334903
• Log P: 1.7336646
• Molar Refractivity: 99.5337 cm^3
• Polarizability: 38.95054 Å^3
• Polar Surface Area: 79.73 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M294565

Camptothecin analog as DNA topoisomerase I inhibitors: a QSAR study. It may also be useful in the design and development of new camptothecin derivatives as DNA topoisomerase I (topo I) inhibitors. A poorly water soluble camptothecin analogue. Antitumor ag

REFERENCES

• Staker, B., et al.: J. Med. Chem., 48, 2336 (2005)
• Verma, R., et al.: Bioorg. Med. Chem., 13, 1059 (2005)