Etoposide phosphateProduct ingredient for Etoposide

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
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
PubChem Compound
6918092
ChemSpider
5293306
BindingDB
50247889
ChEBI
135867
ChEMBL
CHEMBL1200645
ZINC
ZINC000003920020
Wikipedia
Etoposide
Predicted Properties
PropertyValueSource
Water Solubility0.711 mg/mLALOGPS
logP0.84ALOGPS
logP0.51Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)1.46Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area207.36 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity149.89 m3·mol-1Chemaxon
Polarizability62.42 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon