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Compound Detail

CHEMBL89905

4'-DEMETHYLDEOXYPODOPHYLLOTOXIN
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COc1cc([C@@H]2c3cc4c(cc3C[C@H]3COC(=O)[C@@H]32)OCO4)cc(OC)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL89905
Name 4'-DEMETHYLDEOXYPODOPHYLLOTOXIN
Phase Preclinical
Structure Type MOL
InChI Key RFDMNXDDRXVJTM-RQUSPXKASA-N
16
Targets
28
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

384.4
MW (Da)
2.62
ALogP
7
HBA
1
HBD
83.5
PSA (Ų)
0.81
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 C21H20O7
MW 384.38
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 1.66

Activity Summary

IC50 28 meas. best 8.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 8.11 8.11 7.8 1
CCRF S-180
CHEMBL614027
 IC50 7.52 7.52 30.0 1
HeLa
CHEMBL399
 IC50 7.13 5.034 74.0 5
HL-60
CHEMBL383
 IC50 6.96 6.0067 110.0 3
PC-3
CHEMBL390
 IC50 6.85 6.85 140.0 1
LNCaP
CHEMBL612518
 IC50 6.82 6.82 150.0 1
RPMI-8226
CHEMBL614882
 IC50 6.64 6.64 230.0 1
A549
CHEMBL392
 IC50 6.1 5.688 800.0 5
Tubulin
CHEMBL2095182
 IC50 5.7 5.7 2000.0 1
SiHa
CHEMBL612542
 IC50 5.68 4.7733 2070.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.01 5.01 9810.0 1
HepG2
CHEMBL395
 IC50 4.78 4.78 16530.0 1
Kidney
CHEMBL613638
 IC50 4.64 4.64 22990.0 1
Unchecked
CHEMBL612545
 IC50 4.61 4.61 24500.0 1
Liver
CHEMBL613642
 IC50 4.47 4.47 33750.0 1
ADMET
CHEMBL612558
 IC50 4.11 4.11 78520.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 7.8 nM 8.11 Cytotoxicity against human KB cells after 72 hrs by MTT assay 21570846
CCRF S-180 IC50 = 30.0 nM 7.52 Cytotoxicity in S-180 (murine sarcoma) cell was determined. 12873481
HeLa IC50 = 74.0 nM 7.13 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 21570846
HL-60 IC50 = 110.0 nM 6.96 Cytotoxicity against human HL60 cells after 72 hrs by CCK8 method 20071056
PC-3 IC50 = 140.0 nM 6.85 Cytotoxicity against androgen-independent human PC3 cells 17256902
LNCaP IC50 = 150.0 nM 6.82 Cytotoxicity against androgen sensitive human LNCaP cells 17256902
RPMI-8226 IC50 = 230.0 nM 6.64 Cytotoxicity against human RPMI8226 cells after 72 hrs by CCK8 method 20071056
A549 IC50 = 800.0 nM 6.1 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 20071056
A549 IC50 = 1800.0 nM 5.75 Cytotoxicity against human A549 cells assessed as growth inhibition after 48 hrs... 22041063
A549 IC50 = 1800.0 nM 5.75 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 22244588
Tubulin IC50 = 2000.0 nM 5.7 Inhibition of tubulin polymerization in S180 (murine sarcoma) cells. 12873481
SiHa IC50 = 2070.0 nM 5.68 Cytotoxicity against human SiHa cells after 48 hrs by MTT assay 21733601
HL-60 IC50 = 2960.0 nM 5.53 Cytotoxicity against human HL60 cells assessed as growth inhibition after 48 hrs... 22041063
HL-60 IC50 = 2960.0 nM 5.53 Cytotoxicity against human HL60 cells after 48 hrs by CCK-8 assay 22244588
A549 IC50 = 3750.0 nM 5.43 Cytotoxicity against human A549 cells after 48 hrs by MTT assay 21733601
A549 IC50 = 3900.0 nM 5.41 Cytotoxicity against human A549 cells assessed as growth inhibition after 48 hrs... 26873416
HeLa IC50 = 7430.0 nM 5.13 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 21733601
NON-PROTEIN TARGET IC50 = 9810.0 nM 5.01 Cytotoxicity against human HCT8 cells assessed as growth inhibition after 48 hrs... 26873416
HepG2 IC50 = 16530.0 nM 4.78 Cytotoxicity against human HepG2 cells assessed as growth inhibition after 48 hr... 26873416
Kidney IC50 = 22990.0 nM 4.64 Antioxidant activity in Sprague-Dawley rat kidney assessed as lipid peroxidation... 20071056

Literature References

PubMed DOI Target Context # Activities
8277312 10.1021/np50100a011 NON-PROTEIN TARGET 11
20346661 10.1016/j.bmcl.2010.02.108 Mythimna separata 9
8709118 10.1021/jm960023h ADMET 1
26873416 10.1016/j.bmcl.2016.02.013 ADMET 1
8277312 10.1021/np50100a011 P388 1
8277312 10.1021/np50100a011 Artemia 1
3110376 10.1021/np50049a003 Escherichia coli 1
3110376 10.1021/np50049a003 Bacillus subtilis 1
17256902 10.1021/np060430o LNCaP 1
17256902 10.1021/np060430o PC-3 1
8709118 10.1021/jm960023h NON-PROTEIN TARGET 1
12873481 10.1016/s0960-894x(03)00558-4 A549 1
8709118 10.1021/jm960023h Mus musculus 1
12419378 10.1016/s0960-894x(02)00758-8 Mus musculus 1
12419378 10.1016/s0960-894x(02)00758-8 MCF7 1
12419378 10.1016/s0960-894x(02)00758-8 SK-MEL-2 1
12419378 10.1016/s0960-894x(02)00758-8 A549 1
12873481 10.1016/s0960-894x(03)00558-4 Unchecked 1
12873481 10.1016/s0960-894x(03)00558-4 Tubulin 1
12873481 10.1016/s0960-894x(03)00558-4 CCRF S-180 1

Data from ChEMBL 36 via Core Engine