(19S)-19-ethyl-7,19-dihydroxy-8-{[(2H3)methylamino]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: 166594
• Molecular Formular: C22H21N3O5
• Molecular Mass: 407.41924
• Monoisotopic Mass: 407.14812079
• SMILES: c1(c(ccc2c1cc1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)O)CNC
• Canonical SMILES: CNCc1c(O)ccc2c1cc1Cn3c(c1n2)cc1c(c3=O)COC(=O)[C@]1(O)CC
• InChI: InChI=1S/C22H21N3O5/c1-3-22(29)15-7-17-19-11(9-25(17)20(27)14(15)10-30-21(22)28)6-12-13(8-23-2)18(26)5-4-16(12)24-19/h4-7,23,26,29H,3,8-10H2,1-2H3/t22-/m0/s1
• InChIKey: ZWUJOGCYOWLZFL-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-19-ethyl-7,19-dihydroxy-8-{[(^2H₃)methylamino]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-7,19-dihydroxy-8-{[(^2H₃)methylamino]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-4,9-dihydroxy-10-[(methylamino-d3)methyl]-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; N-Desmethyl Topotecan-d3

Database IDs

• CAS Number: 1217633-79-8
• PubChem SID: 162260727
• PubChem CID: 46781194

CALCULATED PROPERTIES

• Acid pKa: 7.8472223
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.5643556
• LogD (pH = 7.4): -1.2112179
• Log P: -0.67615944
• Molar Refractivity: 109.7214 cm^3
• Polarizability: 43.005226 Å^3
• Polar Surface Area: 111.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D294402

A labelled metabolite of Topotecan.

REFERENCES

• Herben, V., et al.: Anti-Cancer Drugs, 9, 411 (1998)
• Hsiang, Y., et al.: Cancer Res., 48, 1722 (1998)
• Hertzberg, R., et al.: J. Med. Chem., 32, 715 (1998)
• Beijnen, J., et al.: J. Pharm. Biomed. Anal., 8, 789 (1998)