Etoposide phosphateProduct ingredient forEtoposide
- Name
- Etoposide phosphate
- Drug Entry
-
Etoposide
A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.
- Accession Number
- DBSALT000070
- Structure
-
Structure for Etoposide phosphate (DBSALT000070)
- Synonyms
- Not Available
- External IDs
- BMY 40481/BMY-40481/VP-16/VP16
- UNII
- 528XYJ8L1N
- CAS Number
- 117091-64-2
- Weight
-
Average: 668.5365
Monoisotopic: 668.15062152 - Chemical Formula
- C29H33O16P
- InChI Key
- LIQODXNTTZAGID-OCBXBXKTSA-N
- 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
- 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[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonic acid
- SMILES
-
[H][C@]12COC(=O)[C@]1([H])[C@]([H])(C1=CC(OC)=C(OP(O)(O)=O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@]2([H])O[C@]1([H])O[C@]2([H])CO[C@@]([H])(C)O[C@@]2([H])[C@]([H])(O)[C@@]1([H])O
- External Links
-
- PubChem Compound
- 6918092
- ChemSpider
- 5293306
- ChEBI
- 135867
- ChEMBL
- CHEMBL1200645
- ZINC
- ZINC000003920020
- Wikipedia
- Etoposide
- Predicted Properties
-
Property Value Source Water Solubility 0.711 mg/mL ALOGPS logP 0.84 ALOGPS logP 0.51 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 1.46 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 207.36 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 149.89 m3·mol-1 Chemaxon Polarizability 62.42 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like规则 Yes Chemaxon
