sodium (2S)-2-(1-{[bis(2H3)methylamino]methyl}-2-hydroxy-8-(hydroxymethyl)-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl)-2-hydroxybutanoate

• ChemBase ID: 178748
• Molecular Formular: C23H24N3NaO6
• Molecular Mass: 461.44293
• Monoisotopic Mass: 461.15627978
• SMILES: c1(c(ccc2c1cc1c(n2)c2n(C1)c(=O)c(c(c2)C(O)(CC)C(=O)[O-])CO)O)CN(C)C.[Na+]
• Canonical SMILES: CCC(c1cc2c3nc4ccc(c(c4cc3Cn2c(=O)c1CO)CN(C)C)O)(C(=O)[O-])O.[Na+]
• InChI: InChI=1S/C23H25N3O6.Na/c1-4-23(32,22(30)31)16-8-18-20-12(9-26(18)21(29)15(16)11-27)7-13-14(10-25(2)3)19(28)6-5-17(13)24-20;/h5-8,27-28,32H,4,9-11H2,1-3H3,(H,30,31);/q;+1/p-1/t23-;/m0./s1
• InChIKey: MKNSEUWGSSBVQF-BQAIUKQQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-(1-{[bis(^2H₃)methylamino]methyl}-2-hydroxy-8-(hydroxymethyl)-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl)-2-hydroxybutanoate
• IUPAC Traditional name: sodium (2S)-2-(1-{[bis(^2H₃)methylamino]methyl}-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl)-2-hydroxybutanoate
• Synonyms: 1-[(Dimethylamino-d6)methyl]-α-ethyl-9,11-dihydro-α,2-dihydroxy-8-(hydroxymethyl)-9-oxo-indolizino[1,2-b]quinoline-7-acetic Acid Monosodium Salt; Topotecan-d6 Carboxylic Acid Sodium Salt

Database IDs

• CAS Number: 1263470-27-4
• PubChem SID: 164234658
• PubChem CID: 46783111

CALCULATED PROPERTIES

• Acid pKa: 3.1319454
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.5399804
• LogD (pH = 7.4): -2.633484
• Log P: -2.54183
• Molar Refractivity: 129.3454 cm^3
• Polarizability: 45.841614 Å^3
• Polar Surface Area: 137.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T542512

The novel labelled carboxylate metabolite of Topotecan.

REFERENCES

• Liu, L., et al.: Annu. Rev. Biochem., 58, 351 (1989)
• Underberg, W., et al.: J. Pharm. Biomed. Anal., 8, 681 (1989)
• Grochow, L., et al.: Drug Metab. Dispos., 20, 706 (1989)
• Scott, D., et al.: Pharm. Res., 10, 1451 (1989)