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Compound Detail

CHEMBL67

COMBRETASTATIN A4
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COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL67
Name COMBRETASTATIN A4
Phase Preclinical
Structure Type MOL
InChI Key HVXBOLULGPECHP-WAYWQWQTSA-N

Known Names

2'-deoxycombretastatin a1 CA4 Combrestatin a4 Combretastatin 4 Combretastatin a-4 Combretastatin a4 NSC-613729 NSC-817373
173
Targets
1,776
Activities
4
Assay Types
23
PK Parameters
20
Publications
8
Known Names

Molecular Properties

316.4
MW (Da)
3.60
ALogP
5
HBA
1
HBD
57.1
PSA (Ų)
0.83
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Achiral

Flags

Natural Product
USAN Stem -stat-

Extended Properties

Molecular Formula C18H20O5
MW 316.35
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.57

Activity Summary

IC50 1,734 meas. best 11.0
EC50 31 meas. best 9.05
Kd 6 meas. best 6.85
Ki 5 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 11.0 7.868 0.0 131
K562
CHEMBL385
 IC50 10.55 7.9334 0.0 38
HCT-116
CHEMBL394
 IC50 10.1 7.9064 0.1 53
HL-60
CHEMBL383
 IC50 10.0 8.288 0.1 25
Unchecked
CHEMBL612545
 IC50 10.0 6.1532 0.1 202
HepG2
CHEMBL395
 IC50 9.85 7.244 0.1 48
ZR-75-1
CHEMBL614393
 IC50 9.62 9.62 0.2 1
HeLa
CHEMBL399
 IC50 9.52 7.8668 0.3 127
U-937
CHEMBL612794
 IC50 9.52 9.26 0.3 4
M21
CHEMBL614117
 IC50 9.4 8.72 0.4 6
KARPAS-422
CHEMBL2366368
 IC50 9.24 9.24 0.6 1
ADMET
CHEMBL612558
 IC50 9.19 8.0118 0.6 11
TMD8
CHEMBL4296503
 IC50 9.18 9.18 0.7 1
CCRF-CEM
CHEMBL382
 IC50 9.15 8.6732 0.7 19
Farage
CHEMBL4483236
 IC50 9.15 9.15 0.7 1
U2OS
CHEMBL615023
 IC50 9.12 8.485 0.8 2
Z-138
CHEMBL4483276
 IC50 9.11 9.11 0.8 1
Jurkat
CHEMBL397
 IC50 9.1 8.38 0.8 10
U2932
CHEMBL4296507
 IC50 9.05 9.05 0.9 1
HUVEC
CHEMBL613979
 EC50 9.05 8.7533 0.9 3
Calu-6
CHEMBL614535
 IC50 9.03 9.03 0.9 1
RS4-11
CHEMBL2366159
 IC50 9.0 9.0 1.0 1
B16
CHEMBL381
 IC50 9.0 8.0744 1.0 9
HT-29
CHEMBL384
 IC50 9.0 6.4893 1.0 75
K562
CHEMBL385
 EC50 9.0 9.0 1.0 1
HCT-15
CHEMBL612263
 IC50 9.0 8.2463 1.0 8
HUVEC
CHEMBL613979
 IC50 9.0 8.1305 1.0 20
HaCaT
CHEMBL614392
 IC50 9.0 8.312 1.0 5
A10
CHEMBL614513
 IC50 9.0 8.32 1.0 2
COLO 205
CHEMBL614561
 IC50 9.0 7.8533 1.0 3
MDA-MB-435
CHEMBL614697
 IC50 9.0 8.1845 1.0 11
SK-OV-3
CHEMBL614925
 IC50 9.0 8.0729 1.0 31
MCF7
CHEMBL387
 IC50 8.98 7.3703 1.0 139
MDA-MB-468
CHEMBL614335
 IC50 8.96 8.5043 1.1 7
NCI-H460
CHEMBL396
 IC50 8.92 7.7895 1.2 19
SK-OV-3
CHEMBL614925
 EC50 8.92 8.715 1.2 2
OVCAR-8
CHEMBL612555
 IC50 8.89 8.2267 1.3 6
NCI/ADR-RES
CHEMBL613829
 IC50 8.89 8.1283 1.3 6
HT-1080
CHEMBL614580
 IC50 8.89 8.2413 1.3 8
Hs-578T
CHEMBL614645
 IC50 8.87 8.87 1.4 1
RL
CHEMBL2366175
 IC50 8.85 8.85 1.4 1
HeLa
CHEMBL399
 EC50 8.85 8.85 1.4 1
KB
CHEMBL398
 IC50 8.82 8.228 1.5 25
SW-620
CHEMBL612262
 IC50 8.82 8.3267 1.5 3
NCI/ADR-RES
CHEMBL613829
 EC50 8.82 8.82 1.5 1
SH-SY5Y
CHEMBL614910
 IC50 8.82 8.625 1.5 4
MOLT-4
CHEMBL614177
 IC50 8.8 8.05 1.6 4
MCF-10A
CHEMBL614321
 IC50 8.8 7.9 1.6 2
ACHN
CHEMBL614519
 IC50 8.8 7.9567 1.6 3
A2780
CHEMBL614004
 IC50 8.78 7.872 1.7 20

Pharmacokinetic Data

Parameter Value Units Species
AUC 920.0 ng.hr.mL-1 Mus musculus
CL 291.36 ml/hr Mus musculus
CL 0.98 mL.min-1.g-1 Homo sapiens
CL 89.5 mL.min-1.kg-1 Homo sapiens
CL 89.5 mL.min-1.kg-1 Homo sapiens
CL 277.0 mL.min-1.g-1 Mus musculus
Cmax 12106.84 nM Mus musculus
Ka 3.35 10'6/M Ovis aries
Ka 3.0 10^8/M Homo sapiens
MRT 0.15 hr Mus musculus
T1/2 0.19 hr Mus musculus
T1/2 0.7 hr Rattus norvegicus
t1/2 - - Rattus norvegicus
t1/2 - - Rattus norvegicus
T1/2 1.0 hr Rattus norvegicus
T1/2 0.04517 hr Homo sapiens
T1/2 0.2317 hr Homo sapiens
T1/2 0.5417 hr Homo sapiens
T1/2 0.2317 hr Homo sapiens
T1/2 0.1583 hr Homo sapiens
T1/2 0.03833 hr Rattus norvegicus
T1/2 3.0 hr Mus musculus
T1/2 5.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.01 nM 11.0 Cytotoxicity against human OVACAR3 cells 17127061
K562 IC50 = 0.0282 nM 10.55 Cytotoxicity against human K562 cells assessed as reduction in cell viability in... 31401010
HCT-116 IC50 = 0.0794 nM 10.1 Cytotoxicity against p53 deficient human HCT116 cells assessed as reduction in c... 31401010
HL-60 IC50 = 0.1 nM 10.0 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 20731355
Unchecked IC50 = 0.1 nM 10.0 Displacement of [3H]colchicine from tubulin by scintillation proximity assay 18783207
HepG2 IC50 = 0.14 nM 9.85 Cytotoxicity against human HepG2 cells 17127061
HCT-116 IC50 = 0.232 nM 9.63 Antiproliferative activity against human HCT116 cells incubated for 48 hrs by MT... 31541870
ZR-75-1 IC50 = 0.24 nM 9.62 Cytotoxicity against ZR-75-1 cell line 17249649
HL-60 IC50 = 0.251 nM 9.6 Antiproliferative activity against human HL60 cells incubated for 48 hrs by MTS ... 31541870
HeLa IC50 = 0.3 nM 9.52 Cytotoxicity against HeLa cell line 17249649
U-937 IC50 = 0.3 nM 9.52 Antiproliferative activity against human U-937 cells incubated for 72 hrs 38171146
U-937 IC50 = 0.3 nM 9.52 Antiproliferative activity against human U-937 cells assessed as inhibition of c... 36162214
HCT-116 IC50 = 0.35 nM 9.46 Cytotoxicity against HCT116 cell line 17249649
NON-PROTEIN TARGET IC50 = 0.4 nM 9.4 Cytotoxicity against human vinblastine-resistant KBV1 cells after 72 hrs by MTT ... 20731355
M21 IC50 = 0.4 nM 9.4 Antiproliferative activity against human M21 cells assessed as cell growth inhib... 36780426
HeLa IC50 = 0.51 nM 9.29 Cytotoxicity against human HeLa cells by MTT assay 19879758
HCT-116 IC50 = 0.547 nM 9.26 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 31401010
KARPAS-422 IC50 = 0.58 nM 9.24 Antiproliferative activity against human KARPAS-422 cells assessed as inhibition... 36502578
NON-PROTEIN TARGET IC50 = 0.58 nM 9.24 Antiproliferative activity in human SK-N-BE cells assessed as cell viability aft... 22329561
ADMET IC50 = 0.64 nM 9.19 Cytotoxicity against P-glycoprotein-overexpressing KB-V1 cell line 17249649

Literature References

PubMed DOI Target Context # Activities
27707624 10.1016/j.bmc.2016.09.063 NON-PROTEIN TARGET 53
35339837 10.1016/j.ejmech.2022.114271 HeLa 36
29291446 10.1016/j.ejmech.2017.11.050 Tubulin 24
26257861 10.1039/c4md00478g NON-PROTEIN TARGET 23
22676247 10.1021/jm300596s Mus musculus 19
31954880 10.1016/j.ejmech.2020.112041 HeLa 19
36252396 10.1016/j.ejmech.2022.114817 A549 17
35635956 10.1016/j.ejmech.2022.114466 HeLa 17
31830637 10.1016/j.ejmech.2019.111949 HepG2 17
28174064 10.1016/j.bmc.2017.01.035 Unchecked 16
30176537 10.1016/j.ejmech.2018.08.074 K562 15
31401010 10.1016/j.bmc.2019.07.048 CCRF-CEM 15
31610372 10.1016/j.ejmech.2019.111732 MDA-MB-468 15
17174089 10.1016/j.bmcl.2006.11.060 Molecular identity unknown 15
20338766 10.1016/j.bmc.2010.03.006 HeLa 14
28803046 10.1016/j.ejmech.2017.07.056 MCF7 14
31830637 10.1016/j.ejmech.2019.111949 ADMET 13
16913727 10.1021/jm060621o SH-SY5Y 13
17291753 10.1016/j.bmcl.2007.01.023 M21 13
27187864 10.1016/j.ejmech.2016.05.012 NON-PROTEIN TARGET 13

Data from ChEMBL 36 via Core Engine