5-[(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}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-10-yl]-3-methoxycyclohexa-3,5-diene-1,2-dione

• ChemBase ID: 168642
• Molecular Formular: C28H28O13
• Molecular Mass: 572.51412
• Monoisotopic Mass: 572.15299096
• SMILES: C1=C(C(=O)C(=O)C=C1[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)OC
• Canonical SMILES: COC1=CC(=CC(=O)C1=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/C28H28O13/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/h3-6,10,14,19-21,23-26,28,31-32H,7-9H2,1-2H3/t10-,14?,19-,20-,21+,23-,24-,25?,26-,28+/m1/s1
• InChIKey: SBLYXIKLMHGUJZ-VRQZPXOLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(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}-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]-3-methoxycyclohexa-3,5-diene-1,2-dione
• IUPAC Traditional name: 5-[(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}-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]-3-methoxycyclohexa-3,5-diene-1,2-dione
• Synonyms: 5-[(5R,5aR,8aR,9S)-9-[(4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-3-methoxy-3,5-cyclohexadiene-1,2-dione; Etoposide o-Quinone; Etoposide 3',4'-Quinone

Database IDs

• CAS Number: 105016-65-7
• PubChem SID: 162262774
• PubChem CID: 71316630

CALCULATED PROPERTIES

• Acid pKa: 12.271962
• H Acceptors: 12
• H Donor: 2
• LogD (pH = 5.5): 0.45869425
• LogD (pH = 7.4): 0.4586885
• Log P: 0.45869434
• Molar Refractivity: 135.1943 cm^3
• Polarizability: 53.27076 Å^3
• Polar Surface Area: 165.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Dark Brown Solid

DETAILS

Toronto Research Chemicals - E933760

Precursor to the semiquinone free radical of Etoposide, believed to inactivate φX174 DNA.

REFERENCES

• Kagan, V., et al.: Biochem., 33, 9651 (1994)
• Gantchev, T., et al.: Mol. Pharmacol., 53, 422 (1994)
• Fan, Y., et al.: Chem. Res. Toxicol., 20, 1067 (1994)
• Alegria, A., et al.: Free Rad. Res., 42, 70 (1994)