(19S)-6,19-diethyl-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: 168452
• Molecular Formular: C22H20N2O4
• Molecular Mass: 376.4052
• Monoisotopic Mass: 376.14230713
• SMILES: c1c(cc2c(c1)cc1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)CC
• Canonical SMILES: CCc1ccc2c(c1)nc1c(c2)Cn2c1cc1c(c2=O)COC(=O)[C@]1(O)CC
• InChI: InChI=1S/C22H20N2O4/c1-3-12-5-6-13-8-14-10-24-18(19(14)23-17(13)7-12)9-16-15(20(24)25)11-28-21(26)22(16,27)4-2/h5-9,27H,3-4,10-11H2,1-2H3/t22-/m0/s1
• InChIKey: SGXXQRSXMWIURP-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-6,19-diethyl-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: (19S)-6,19-diethyl-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: 11-Ethyl Camptothecin; (4S)-4,8-Diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Database IDs

• CAS Number: 185807-29-8
• PubChem SID: 162262584
• PubChem CID: 29979717

CALCULATED PROPERTIES

• Acid pKa: 11.709084
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1749058
• LogD (pH = 7.4): 2.17817
• Log P: 2.1782334
• Molar Refractivity: 104.1347 cm^3
• Polarizability: 40.791286 Å^3
• Polar Surface Area: 79.73 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E900835

An antitumor substituted Camptothecin derivative.

REFERENCES

• Brangi, M., et al.: Cancer Res., 59 5938 (1999)
• Miyake, K., et al.: Cancer Res., 59, 8 (1999)
• Bom, D., et al.: J. Med. Chem., 43, 3970 (1999)
• Gamcsik, M., et al.: Mol. Cancer Ther., 1, 11 (2001).