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(10R,11R,15R,16S)-16-{[(2R,4aR,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
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ChemBase ID:
179694
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Molecular Formular:
C29H32O13
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Molecular Mass:
588.55658
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Monoisotopic Mass:
588.18429108
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SMILES and InChIs
SMILES:
[C@@H]12[C@@H](c3c([C@H]([C@H]1C(=O)OC2)c1cc(c(c(c1)OC)O)OC)cc1c(c3)OCO1)OC1[C@@H]([C@H]([C@H]2[C@H](O1)CO[C@H](O2)C)O)O
Canonical SMILES:
COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)OC1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@H]1O)O)C
InChI:
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29?/m1/s1
InChIKey:
VJJPUSNTGOMMGY-PJVTZUROSA-N
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Cite this record
CBID:179694 http://www.chembase.cn/molecule-179694.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(10R,11R,15R,16S)-16-{[(2R,4aR,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
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IUPAC Traditional name
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(10R,11R,15R,16S)-16-{[(2R,4aR,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
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Synonyms
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Abiposid
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Amizide
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Citodox
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Etopophos
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Exitop
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Toposar
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Vepesid
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Vepeside
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Vespid
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Etoposide
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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9.329948
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H Acceptors
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12
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H Donor
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3
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LogD (pH = 5.5)
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1.1603667
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LogD (pH = 7.4)
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1.155394
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Log P
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1.1604304
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Molar Refractivity
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139.0212 cm3
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Polarizability
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55.93246 Å3
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Polar Surface Area
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160.83 Å2
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Rotatable Bonds
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5
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Lipinski's Rule of Five
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false
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PROPERTIES
PROPERTIES
Pharmacology Properties
Product Information
Bioassay(PubChem)
Mechanism of Action
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DNA topoisomerase II inhibitor
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Show
data source
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Application(s)
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Antineoplastic agent
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Show
data source
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REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
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- • Arnold, A.M. et al., Lancet, 1981, 2, 912, (rev)
- • Issell, B.F. et al., Etoposide (VP-16): Curr. Status New Dev. [Pap. Symp], (Eds.), Academic Press, 1984, (book)
- • Clark, P.I. et al., Clin. Pharmacokinet., 1987, 12, 223, (rev, pharmacol, metab, tox)
- • Holthuis, J.J.M. et al., Anal. Profiles Drug Subst., 1989, 18, 121, (rev)
- • Sthelin, H.F. et al., Prog. Drug Res., 1989, 33, 169, (rev)
- • Sthelin, H.F. et al., Cancer Res., 1991, 51, 5, (rev)
- • Semin. Oncol., Suppl. 13, 1992, 19, (rev)
- • von Wartburg, A. et al., Chron. Drug Discovery, 1993, 3, 349, (rev)
- • Cragg, G. et al., Anticancer Drugs: Antimetabolite Metabolism and Natural Anticancer Agents, (ed. Powis, G.), Pergamon Press, 1994, 364, (rev)
- • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 10960, (synonyms)
- • Hainsworth, J.D. et al., Ann. Oncol., 1995, 6, 325, (pharmacol, rev)
- • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 532
- • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EAV500
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PATENTS
PATENTS
PubChem Patent
Google Patent