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117091-64-2 molecular structure
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{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 and InChIs

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

Cite this record

CBID:168641 http://www.chembase.cn/molecule-168641.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[7.7.0.03,7.011,15]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[7.7.0.03,7.011,15]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
CAS Number
117091-64-2
PubChem SID
162262773
PubChem CID
6918092

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC E933755 external link Add to cart
PubChem 6918092 external link
Data Source Data ID Price
TRC
E933755 external link Add to cart Please log in.
Data Source Data ID
PubChem 6918092 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.4587805  H Acceptors 14 
H Donor LogD (pH = 5.5) -1.908058 
LogD (pH = 7.4) -2.862664  Log P 0.50656533 
Molar Refractivity 149.8941 cm3 Polarizability 60.409317 Å3
Polar Surface Area 207.36 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - E933755 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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