(10R,11R)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-[4-hydroxy-3-(2H3)methoxy-5-methoxyphenyl]-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one

• ChemBase ID: 178144
• Molecular Formular: C32H32O13S
• Molecular Mass: 656.65368
• Monoisotopic Mass: 656.15636208
• SMILES: c1c(c(c(cc1[C@H]1[C@@H]2C(C(c3c1cc1c(c3)OCO1)O[C@H]1[C@H]([C@H]([C@H]3[C@H](O1)CO[C@H](O3)c1cccs1)O)O)COC2=O)OC)O)OC
• Canonical SMILES: COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OCC2C(c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@@H]1O)O)c1cccs1
• InChI: InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16?,21-,23-,24+,26-,27-,28?,29-,31-,32+/m1/s1
• InChIKey: NRUKOCRGYNPUPR-VIEVQKDASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-[4-hydroxy-3-(^2H₃)methoxy-5-methoxyphenyl]-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one
• IUPAC Traditional name: (10R,11R)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-[4-hydroxy-3-(^2H₃)methoxy-5-methoxyphenyl]-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one
• Synonyms: 5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl-d3)-9-[[4,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; EPT-d3; NSC 122819-d3; S 122819-d3; Tenoposide-d3; VM 26-d3; Vehem-d3; Vehem-Sandoz-d3; Vumon-d3; Teniposide-d3

Database IDs

• PubChem SID: 164234054
• PubChem CID: 71752355

CALCULATED PROPERTIES

• Acid pKa: 9.329948
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 2.7839653
• LogD (pH = 7.4): 2.7789927
• Log P: 2.7840292
• Molar Refractivity: 155.6095 cm^3
• Polarizability: 62.345394 Å^3
• Polar Surface Area: 160.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T018402

A labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic.

REFERENCES

• Stahlen, H., Eur. J. Cancer, 6, 303 (1970)
• Hacker, M., et al.: Cancer Res., 37, 3287 (1970)
• Clark, P.I., et al.: Clin. Pharmacokinet., 12, 223 (1970)