General Information of the Compound
Compound ID
CP0036823
Compound Name
(-)-etoposide
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Synonyms
(-)-Etoposide
33419-42-0
4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
4'-Demethylepipodophyllotoxin ethylidene-beta-D-glucoside
4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin
4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside
4-Demethylepipodophyllotoxin-beta-D-ethylideneglucoside
CCRIS 2392
DEMETHY-EPIPODOPHYLLOTOXIN, ETHYLIDENE GLUCOSIDE
Demethyl EpipodophyllotoxinEthylidine Glucoside
Demethyl-epiodophyllotoxin ethylidene glucoside
Demethylepipodophyllotoxin-beta-D-ethylideneglucoside
E0675
EINECS 251-509-1
Epipodophyllotoxin VP-162
Epipodophyllotoxin VP-16213
Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside
Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside (8CI)
Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
Eposide
Eposin
Eposin (TN)
Eposin, Vepesid, VP-16, Toposar, Etoposide
Etopol
Etopophos (TN)
Etopophos (phosphate salt)
Etoposide
Etoposide (JP15/USP/INN)
Etoposide (VP16)
Etoposide [USAN:INN:BAN:JAN]
Etoposido
Etoposido [INN-Spanish]
Etoposidum
Etoposidum [INN-Latin]
Etosid
HSDB 6517
Lastet
NK 171
NSC 141540
NSC-141540
Toposar
Trans-Etoposide
UNII-6PLQ3CP4P3
VP 16
VP 16 (pharmaceutical)
VP 16-213
VP 16213
VP-16
VP-16 (TN)
VP-16-213
VePESID (TN)
VePesid
Vepesid (TN)
Vepesid J
Vepeside
Zuyeyidal
etoposide
trans-Etoposide
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Structure
Formula
C29H32O13
Molecular Weight
588.562
Canonical SMILES
COc1cc(cc(OC)c1O)[C@H]1[C@@H]2[C@H](COC2=O)[C@H](O[C@@H]2O[C@@H]3CO[C@@H](C)O[C@H]3[C@H](O)[C@H]2O)c2cc3OCOc3cc12
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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
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InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
CAS
121471-01-0
136598-18-0
201594-04-9
35317-32-9
51854-34-3
76576-58-4
33419-42-0
Physicochemical Property
logP
1.3386
Rotatable Bonds
5
Heavy Atom Count
42
Polar Areas
160.83
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
13
Complexity
42

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 36462
SID: 14935915
ChEMBL ID
CHEMBL44657
DrugBank ID
DB00773
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01546, ATP-dependent translocase ABCB1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000009 LLC-PK1 Sus scrofa (Pig)  1
1
IC50 > 50000 nM
   TI
   LI
   LO
   TS
Protein ID: PT01685, ATP-dependent translocase ABCB1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000009 LLC-PK1 Sus scrofa (Pig)  1
1
IC50 > 50000 nM
   TI
   LI
   LO
   TS
Protein ID: PT06079, ATP-dependent translocase ABCB1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000009 LLC-PK1 Sus scrofa (Pig)  1
1
IC50 > 50000 nM
   TI
   LI
   LO
   TS
Protein ID: PT01014, Caspase-3
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000366 UACC-62 Homo sapiens (Human)  1
1
IC50 > 50000 nM
   TI
   LI
   LO
   TS
CL000038 B16-F10 Mus musculus (Mouse)  1
1
IC50 > 50000 nM
   TI
   LI
   LO
   TS
CL000028 PC-12 Homo sapiens (Human)  1
1
IC50 < 1000 nM
   TI
   LI
   LO
   TS
CL000289 SK-N-SH Homo sapiens (Human)  1
1
IC50 < 1000 nM
   TI
   LI
   LO
   TS
CL000018 HL-60 Homo sapiens (Human)  1
1
IC50 < 1000 nM
   TI
   LI
   LO
   TS
CL000100 U-937 Homo sapiens (Human)  1
1
IC50 < 1000 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 > 50000 nM
Protein ID: PT06109, Geminin
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000015 SW480 Homo sapiens (Human)  1
1
Potency ~ 2310.9 nM
   TI
   LI
   LO
   TS
Protein ID: PT00991, Histone deacetylase 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000023 BTI-Tn-5B1-4 Trichoplusia ni (Cabbage looper)  1
1
IC50 > 33981.24235 nM
   TI
   LI
   LO
   TS
Protein ID: PT06101, Latent membrane protein 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
AC50 = 26497 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Etoposide )
Drug Name Etoposide
Company Bristol Myers Squibb Co Pharmaceutical Research Institute
Indication
Solid tumour/cancer
Approved
Drug 2 ( Etoposide )
Drug Name Etoposide
Indication
Testicular cancer
Approved
Coronavirus Disease 2019 (COVID-19)
Phase 2