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Compound Detail

CHEMBL31929

4'-DEMETHYLEPIPODOPHYLLOTOXIN
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COc1cc([C@@H]2c3cc4c(cc3[C@@H](O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL31929
Name 4'-DEMETHYLEPIPODOPHYLLOTOXIN
Phase Preclinical
Structure Type MOL
InChI Key YVCVYCSAAZQOJI-JHQYFNNDSA-N
16
Targets
20
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

400.4
MW (Da)
2.11
ALogP
8
HBA
2
HBD
103.7
PSA (Ų)
0.76
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H20O8
MW 400.38
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.66

Activity Summary

IC50 20 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
H9
CHEMBL614806
 IC50 7.16 7.16 70.0 1
HT-1080
CHEMBL614580
 IC50 6.96 6.96 110.0 1
HT-29
CHEMBL384
 IC50 6.82 6.82 150.0 1
HaCaT
CHEMBL614392
 IC50 6.8 6.8 160.0 1
M21
CHEMBL614117
 IC50 6.77 6.77 170.0 1
HL-60
CHEMBL383
 IC50 6.09 6.09 820.0 1
HeLa
CHEMBL399
 IC50 6.01 5.1233 980.0 3
ADMET
CHEMBL612558
 IC50 4.88 4.88 13040.0 1
HepG2
CHEMBL395
 IC50 4.73 4.655 18740.0 2
A549
CHEMBL392
 IC50 4.72 4.5 19000.0 2
L02
CHEMBL4296457
 IC50 4.71 4.71 19400.0 1
HMEC
CHEMBL614734
 IC50 4.71 4.71 19600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.67 4.67 21260.0 1
MRC5
CHEMBL614181
 IC50 4.67 4.67 21300.0 1
Unchecked
CHEMBL612545
 IC50 4.6 4.6 25100.0 1
MCF7
CHEMBL387
 IC50 4.52 4.52 30100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
H9 IC50 = 70.0 nM 7.16 Cytotoxicity against H9 cell line -
HT-1080 IC50 = 110.0 nM 6.96 Antiproliferative activity against human HT-1080 cells assessed as inhibition of... 34837817
HT-29 IC50 = 150.0 nM 6.82 Antiproliferative activity against human HT-29 cells assessed as inhibition of c... 34837817
HaCaT IC50 = 160.0 nM 6.8 Antiproliferative activity against human HaCaT cells assessed as inhibition of c... 34837817
M21 IC50 = 170.0 nM 6.77 Antiproliferative activity against human M21 cells assessed as inhibition of cel... 34837817
HL-60 IC50 = 820.0 nM 6.09 Cytotoxicity against human HL60 cells by MTT assay 19111464
HeLa IC50 = 980.0 nM 6.01 Cytotoxicity agaisnt human HeLa cells by SRB assay 19111464
ADMET IC50 = 13040.0 nM 4.88 Cytotoxicity against human HL-7702 cells after 48 hrs by MTT assay 24775914
HeLa IC50 = 15960.0 nM 4.8 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 24775914
HepG2 IC50 = 18740.0 nM 4.73 Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay 24775914
A549 IC50 = 19000.0 nM 4.72 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 30265994
L02 IC50 = 19400.0 nM 4.71 Cytotoxicity against human HL7702 cells after 48 hrs by MTT assay 30265994
HMEC IC50 = 19600.0 nM 4.71 Cytotoxicity against HMEC after 48 hrs by MTT assay 30265994
NON-PROTEIN TARGET IC50 = 21260.0 nM 4.67 Cytotoxicity against human BGC823 cells after 48 hrs by MTT assay 24775914
MRC5 IC50 = 21300.0 nM 4.67 Cytotoxicity against human MRC5 cells after 48 hrs by MTT assay 30265994
Unchecked IC50 = 25100.0 nM 4.6 Cytotoxicity against human H8 cells after 48 hrs by MTT assay 30265994
HepG2 IC50 = 26100.0 nM 4.58 Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay 30265994
HeLa IC50 = 27800.0 nM 4.56 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 30265994
MCF7 IC50 = 30100.0 nM 4.52 Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay 30265994
A549 IC50 = 52080.0 nM 4.28 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 24775914

Literature References

PubMed DOI Target Context # Activities
- 10.1016/j.indcrop.2012.06.045 Mythimna separata 4
- 10.1016/S0960-894X(97)10108-1 H9 2
24775914 10.1016/j.bmc.2014.03.048 HepG2 2
24775914 10.1016/j.bmc.2014.03.048 HeLa 2
24775914 10.1016/j.bmc.2014.03.048 A549 2
2550587 10.1021/np50063a021 DNA topoisomerase 2-alpha 2
24775914 10.1016/j.bmc.2014.03.048 NON-PROTEIN TARGET 2
1331331 10.1021/np50086a011 DNA topoisomerase 2-alpha 2
24775914 10.1016/j.bmc.2014.03.048 ADMET 2
2849640 10.1021/np50059a014 Unchecked 1
2849640 10.1021/np50059a014 KB 1
9834179 10.1021/np980136z NON-PROTEIN TARGET 1
9834179 10.1021/np980136z ADMET 1
2537424 10.1021/jm00123a016 DNA topoisomerase II 1
2550587 10.1021/np50063a021 KB 1
34837817 10.1016/j.bmc.2021.116501 HaCaT 1
2537424 10.1021/jm00123a016 ADMET 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
3016271 10.1021/jm00158a042 DNA topoisomerase II 1

Data from ChEMBL 36 via Core Engine