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

• ChemBase ID: 166486
• Molecular Formular: C28H30O13
• Molecular Mass: 574.53
• Monoisotopic Mass: 574.16864102
• 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)C)O)O)COC2=O)O)O)OC
• Canonical SMILES: COc1cc(cc(c1O)O)[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)C
• InChI: InChI=1S/C28H30O13/c1-10-35-8-19-26(39-10)23(31)24(32)28(40-19)41-25-13-6-17-16(37-9-38-17)5-12(13)20(21-14(25)7-36-27(21)33)11-3-15(29)22(30)18(4-11)34-2/h3-6,10,14,19-21,23-26,28-32H,7-9H2,1-2H3/t10-,14?,19-,20-,21+,23-,24-,25?,26-,28+/m1/s1
• InChIKey: CYOJPLOJEPTJMM-VRQZPXOLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(3,4-dihydroxy-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-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(3,4-dihydroxy-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-(3,4-Dihydroxy-5-methoxyphenyl)-9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; 3'-Demethyl Etoposide; 3'-O-Demethyletoposide; 3'-O-Desmethyl Etoposide

Database IDs

• CAS Number: 100007-54-3
• PubChem SID: 162260619
• PubChem CID: 71315755

CALCULATED PROPERTIES

• Acid pKa: 9.473689
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 1.0144906
• LogD (pH = 7.4): 1.0109118
• Log P: 1.0145364
• Molar Refractivity: 134.5389 cm^3
• Polarizability: 54.044 Å^3
• Polar Surface Area: 171.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Light Brown Solid
• Melting Point: 192-194°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291970

An Etoposide (E933750) metabolite

REFERENCES

• Relling, M., et al.: Mol. Pharmacol., 45, 352 (1994)
• Lovett, B., et al.: Biochem., 40, 1159 (1994)
• Zhuo, X., et al.: Drug Metab. Disposition, 32, 993 (1994)
• Fan, Y., et al.: Chem. Res. Toxicol., 19, 937 (1994)