{4-[(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonic acid

• ChemBase ID: 168641
• Molecular Formular: C29H33O16P
• Molecular Mass: 668.536481
• Monoisotopic Mass: 668.15062161
• SMILES: c1c(c(c(cc1[C@H]1[C@@H]2[C@@H]([C@@H](c3c1cc1c(c3)OCO1)O[C@H]1[C@H]([C@H]([C@H]3[C@H](O1)CO[C@H](O3)C)O)O)COC2=O)OC)OP(=O)(O)O)OC
• Canonical SMILES: COc1cc(cc(c1OP(=O)(O)O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@@H]1O)O)C
• InChI: InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1
• InChIKey: LIQODXNTTZAGID-OCBXBXKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonic acid
• IUPAC Traditional name: 4-[(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxyphosphonic acid
• Synonyms: [5R-[5α,5aβ,8aα,9β(R*)]]-5-[3,5-Dimethoxy-4-(phosphonooxy)phenyl]-9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; BMY 40481; Etopofos; Etopophos; Etoposide 4'-Phosphate; (5R,5aR,8aR,9S)-5-[3,5-Dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; Etoposide Phosphate

Database IDs

• CAS Number: 117091-64-2
• PubChem SID: 162262773
• PubChem CID: 6918092

CALCULATED PROPERTIES

• Acid pKa: 1.4587805
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): -1.908058
• LogD (pH = 7.4): -2.862664
• Log P: 0.50656533
• Molar Refractivity: 149.8941 cm^3
• Polarizability: 60.409317 Å^3
• Polar Surface Area: 207.36 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E933755

A bioequivalent prodrug of the DNA topoisomerase II inhibitor Etoposide (E933750). Antineoplastic used in the treatment of a wide variety of hematological malignancies and solid tumors.

REFERENCES

• Kaul, S. et al.: J. Clin. Pharmacol., 13, 2835 (1995)
• J. Pharmakin. Biopharmac., 24, 313 (1995)
• Brooks, D.J. et al.: Anti-Cancer Drugs, 6, 637 (1995)