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Compound Detail

CHEMBL63970

DESOXYPODOPHYLLOTOXIN
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COc1cc([C@@H]2c3cc4c(cc3C[C@H]3COC(=O)[C@@H]32)OCO4)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL63970
Name DESOXYPODOPHYLLOTOXIN
Phase Preclinical
Structure Type MOL
InChI Key ZGLXUQQMLLIKAN-SVIJTADQSA-N
18
Targets
38
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

398.4
MW (Da)
2.92
ALogP
7
HBA
0
HBD
72.5
PSA (Ų)
0.73
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H22O7
MW 398.41
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.48

Activity Summary

IC50 37 meas. best 9.0
EC50 1 meas. best 8.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.0 6.0656 1.0 9
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 8.71 8.71 1.9 1
KB
CHEMBL398
 IC50 8.52 8.285 3.0 2
CV-1
CHEMBL613507
 IC50 8.22 8.22 6.0 1
HT-29
CHEMBL384
 IC50 8.22 8.0 6.0 2
MCF7
CHEMBL387
 IC50 8.22 8.22 6.0 1
HeLa
CHEMBL399
 IC50 8.16 5.88 6.9 4
GLC4 cell line
CHEMBL612707
 IC50 8.1 7.51 8.0 2
P388
CHEMBL389
 IC50 8.0 8.0 10.0 1
HCT-116
CHEMBL394
 IC50 7.84 7.84 14.5 1
K562
CHEMBL385
 IC50 7.8 7.8 16.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.75 7.75 18.0 1
Human alphaherpesvirus 1
CHEMBL377
 IC50 7.6 7.6 25.0 1
LNCaP
CHEMBL612518
 IC50 7.52 7.52 30.0 1
PC-3
CHEMBL390
 IC50 7.5 7.5 32.0 1
A549
CHEMBL392
 IC50 6.33 6.0167 470.0 3
HL-60
CHEMBL383
 IC50 6.33 6.33 470.0 2
SiHa
CHEMBL612542
 IC50 5.7 5.3033 1980.0 3
Tubulin
CHEMBL2095182
 IC50 5.62 5.62 2400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1435.06 mL.min-1.kg-1 Homo sapiens
T1/2 0.01867 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 Inhibition of PI3K (unknown origin) 38295689
NON-PROTEIN TARGET EC50 = 1.93 nM 8.71 Antiproliferative activity against mouse ependymoma cells harboring EPHB2 after ... 24617915
KB IC50 = 3.0 nM 8.52 Cytotoxicity against human KB cells assessed as inhibition of cell proliferation... 22429510
HT-29 IC50 = 6.0 nM 8.22 Antineoplastic activity against HT-29 (human colon carcinoma) cell line. -
CV-1 IC50 = 6.0 nM 8.22 Antineoplastic activity against CV-1 (monkey kidney fibroblast) cell line. -
MCF7 IC50 = 6.0 nM 8.22 Antiproliferative activity against human MCF7 cells measured after 72 hrs by MTT... 36471625
HeLa IC50 = 6.9 nM 8.16 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 21570846
GLC4 cell line IC50 = 8.0 nM 8.1 Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using ... 7783142
KB IC50 = 8.9 nM 8.05 Cytotoxicity against human KB cells after 72 hrs by MTT assay 21570846
P388 IC50 = 10.0 nM 8.0 Antineoplastic activity against P-388 (murine leukemia) cell line. -
HCT-116 IC50 = 14.5 nM 7.84 Antiproliferative activity against human HCT-116 cells measured after 72 hrs by ... 36471625
K562 IC50 = 16.0 nM 7.8 Antiproliferative activity against human K562 cells measured after 72 hrs by MTT... 36471625
HT-29 IC50 = 16.6 nM 7.78 Antiproliferative activity against human HT-29 cells measured after 72 hrs by MT... 36471625
NON-PROTEIN TARGET IC50 = 18.0 nM 7.75 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 27214307
Human alphaherpesvirus 1 IC50 = 25.0 nM 7.6 Antiviral activity against HSV1 infected in monkey CV-1 cells assessed as inhibi... 9834179
LNCaP IC50 = 30.0 nM 7.52 Cytotoxicity against androgen sensitive human LNCaP cells 17256902
PC-3 IC50 = 32.0 nM 7.5 Cytotoxicity against androgen-independent human PC3 cells 17256902
GLC4 cell line IC50 = 120.0 nM 6.92 Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using ... 7783142
HL-60 IC50 = 470.0 nM 6.33 Cytotoxicity against human HL60 cells after 48 hrs by CCK-8 assay 22244588
HL-60 IC50 = 470.0 nM 6.33 Cytotoxicity against human HL60 cells assessed as growth inhibition after 48 hrs... 22041063

Literature References

PubMed DOI Target Context # Activities
19501508 10.1016/j.bmcl.2009.05.093 HeLa 20
8277312 10.1021/np50100a011 NON-PROTEIN TARGET 11
20346661 10.1016/j.bmcl.2010.02.108 Mythimna separata 9
22257529 10.1016/j.bmc.2011.12.038 HL-60 8
6677713 10.1021/np50030a003 Hepatocyte 6
21733601 10.1016/j.ejmech.2011.06.004 A549 4
26938998 10.1021/acs.jnatprod.5b00873 NON-PROTEIN TARGET 4
17998150 10.1016/j.ejmech.2007.09.005 Cytochrome P450 3A4 3
22429510 10.1016/j.bmc.2012.02.043 KB 3
6298369 10.1021/np50024a015 Measles morbillivirus 3
24617915 10.1021/np4009706 No relevant target 2
9834179 10.1021/np980136z Human alphaherpesvirus 1 2
6298369 10.1021/np50024a015 Vero 2
23618708 10.1016/j.bmc.2013.03.064 Unchecked 2
23200248 10.1016/j.bmcl.2012.10.135 Unchecked 2
7783142 10.1021/jm00012a010 GLC4 cell line 2
27073050 10.1016/j.bmc.2016.04.001 Unchecked 2
19501508 10.1016/j.bmcl.2009.05.093 Unchecked 2
22429510 10.1016/j.bmc.2012.02.043 Unchecked 2
25462232 10.1016/j.ejmech.2014.10.041 Unchecked 2

Data from ChEMBL 36 via Core Engine