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Compound Detail

CHEMBL307794

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CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc4c(cc3nc2-1)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL307794
Phase Preclinical
Structure Type MOL
InChI Key RPFYDENHBPRCTN-NRFANRHFSA-N
21
Targets
36
Activities
3
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.4
MW (Da)
1.81
ALogP
8
HBA
1
HBD
99.9
PSA (Ų)
0.49
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H16N2O6
MW 392.37
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 0.98

Activity Summary

IC50 29 meas. best 9.03
EC50 6 meas. best 9.44
Kd 1 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 EC50 9.44 9.44 0.4 1
A549
CHEMBL392
 EC50 9.07 9.07 0.9 1
SW-620
CHEMBL612262
 IC50 9.03 8.54 0.9 2
NSCLC
CHEMBL612554
 EC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 EC50 8.64 8.51 2.3 2
NCI-H460
CHEMBL396
 IC50 8.52 8.52 3.0 1
HCT-8
CHEMBL613510
 IC50 8.3 8.3 5.0 1
HCT-116
CHEMBL394
 IC50 8.3 7.965 5.0 2
EKVX
CHEMBL614487
 IC50 8.22 8.22 6.0 1
H69AR
CHEMBL5209893
 IC50 8.2 8.2 6.3 1
NCI-H446
CHEMBL612440
 IC50 8.18 7.9867 6.6 3
PC-3
CHEMBL390
 IC50 8.09 8.09 8.1 1
A549
CHEMBL392
 IC50 8.05 7.4733 9.0 3
HeLa
CHEMBL399
 IC50 8.02 7.755 9.6 2
HepG2
CHEMBL395
 IC50 7.97 7.685 10.6 2
NCI-H69
CHEMBL614805
 IC50 7.8 7.8 15.8 1
Bel-7402
CHEMBL614279
 IC50 7.66 7.66 21.8 1
SH-SY5Y
CHEMBL614910
 IC50 7.62 7.62 24.2 1
DNA topoisomerase 1
CHEMBL1781
 IC50 7.57 7.4 27.0 3
MCF7
CHEMBL387
 IC50 7.49 7.345 32.2 2
Probable ATP-dependent RNA helicase DDX5
CHEMBL4295722
 Kd 7.46 7.46 34.4 1
2008
CHEMBL612818
 IC50 7.43 7.43 37.3 1
DNA topoisomerase 1
CHEMBL1781
 EC50 7.3 7.3 50.0 1
U-87 MG
CHEMBL614247
 IC50 6.96 6.96 108.6 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 82.0 ng.hr.mL-1 Mus musculus
CL 900.0 mL.min-1.kg-1 Mus musculus
Cmax 109.59 nM Mus musculus
T1/2 0.2 hr -
T1/2 1.8 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 EC50 = 0.36 nM 9.44 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 38421819
A549 EC50 = 0.86 nM 9.07 Antiproliferative activity against human A549 cells assessed as reduction in cel... 38421819
SW-620 IC50 = 0.93 nM 9.03 Antiproliferative activity against human SW-620 cells assessed as inhibition of ... 35932565
NSCLC EC50 = 1.0 nM 9.0 Cytotoxicity against human NSCLC cells 34175539
Unchecked EC50 = 2.28 nM 8.64 Antiproliferative activity against human HCT116-SN6 cells assessed as reduction ... 38421819
NCI-H460 IC50 = 3.0 nM 8.52 Antiproliferative activity against human NCI-H460 cells assessed as reduction in... 38092421
Unchecked EC50 = 4.14 nM 8.38 Antiproliferative activity against human HCT116-G7 cells assessed as reduction i... 38421819
HCT-8 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HCT-8 cells assessed as inhibition of c... 38092421
HCT-116 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 38092421
EKVX IC50 = 6.0 nM 8.22 Antiproliferative activity against human EKVX cells assessed as cell growth inhi... 38092421
H69AR IC50 = 6.29 nM 8.2 Antiproliferative activity against human NCI-H69AR cells assessed as inhibition ... 35932565
NCI-H446 IC50 = 6.61 nM 8.18 Antiproliferative activity against etoposide/cisplatin combination-resistant hum... 35932565
PC-3 IC50 = 8.1 nM 8.09 Concentration required to inhibit growth of human prostate PC-3 carcinoma cell l... 15454230
NCI-H446 IC50 = 8.87 nM 8.05 Antiproliferative activity against human NCI-H446 cells assessed as inhibition o... 35932565
A549 IC50 = 9.0 nM 8.05 Antiproliferative activity against human A549 cells assessed as reduction in cel... 38092421
SW-620 IC50 = 9.0 nM 8.05 Antiproliferative activity against human SW620 cells assessed as reduction in ce... 38092421
HeLa IC50 = 9.6 nM 8.02 Concentration required to inhibit growth of human cervical HeLa carcinoma cell l... 15454230
HepG2 IC50 = 10.64 nM 7.97 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 35932565
NCI-H69 IC50 = 15.81 nM 7.8 Antiproliferative activity against human NCI-H69 cells assessed as inhibition of... 35932565
NCI-H446 IC50 = 18.54 nM 7.73 Antiproliferative activity against Irinotecan-resistant human NCI-H446 cells ass... 35932565

Literature References

PubMed DOI Target Context # Activities
38100041 10.1021/acs.jmedchem.3c01589 HCT-116 133
35932565 10.1016/j.ejmech.2022.114610 NCI-H446 16
35932565 10.1016/j.ejmech.2022.114610 H69AR 10
38092421 10.1021/acs.jmedchem.3c01130 ADMET 4
35932565 10.1016/j.ejmech.2022.114610 Unchecked 2
8410981 10.1021/jm00070a013 Mus musculus 2
38421819 10.1021/acs.jmedchem.3c02115 A549 2
15454230 10.1016/j.bmcl.2004.08.010 DNA topoisomerase 1 2
38421819 10.1021/acs.jmedchem.3c02115 Unchecked 2
38421819 10.1021/acs.jmedchem.3c02115 HCT-116 2
15454230 10.1016/j.bmcl.2004.08.010 PC-3 1
35932565 10.1016/j.ejmech.2022.114610 MCF7 1
35932565 10.1016/j.ejmech.2022.114610 SH-SY5Y 1
35932565 10.1016/j.ejmech.2022.114610 SW-620 1
35932565 10.1016/j.ejmech.2022.114610 2008 1
15454230 10.1016/j.bmcl.2004.08.010 HeLa 1
15454230 10.1016/j.bmcl.2004.08.010 ADMET 1
9632354 10.1021/jm9605445 DNA topoisomerase 1 1
8410981 10.1021/jm00070a013 DNA topoisomerase 1 1
8410981 10.1021/jm00070a013 HT-29 1

Data from ChEMBL 36 via Core Engine