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Compound Detail

CHEMBL1206232

FOSBRETABULIN
🧪 Phase III
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🧪 Phase III
COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1OP(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1206232
Name FOSBRETABULIN
Phase Phase III
Structure Type MOL
InChI Key WDOGQTQEKVLZIJ-WAYWQWQTSA-N
Active Moiety CHEMBL67

Known Names

Combretastatin a-4 phosphate Combretastatin a4 phosphate Fosbretabulin Fosbretabulina Fosbretabuline Phosbretabulin
8
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
5
Indications

Molecular Properties

396.3
MW (Da)
3.36
ALogP
6
HBA
2
HBD
103.7
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product Prodrug
USAN Stem -bulin; fos-
USAN Year 2008

Extended Properties

Molecular Formula C18H21O8P
MW 396.33
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.65

Indications

Thyroid Neoplasms Neoplasms Neuroendocrine Tumors Ovarian Neoplasms Ovarian Neoplasms

Activity Summary

IC50 10 meas. best 8.35
EC50 1 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SK-OV-3
CHEMBL614925
 IC50 8.35 8.265 4.5 2
HeLa
CHEMBL399
 IC50 8.33 8.285 4.7 2
Unchecked
CHEMBL612545
 EC50 8.15 8.15 7.0 1
MGC-803
CHEMBL3706566
 IC50 7.7 7.7 20.0 1
PC-3
CHEMBL390
 IC50 7.48 7.48 33.0 1
HCT-116
CHEMBL394
 IC50 7.38 7.38 42.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.19 5.19 6400.0 2
EA.hy 926
CHEMBL4296410
 IC50 5.19 5.19 6400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SK-OV-3 IC50 = 4.5 nM 8.35 Antiproliferative activity against human SKOV3 cells by sulforhodamine B assay 20973488
HeLa IC50 = 4.7 nM 8.33 Antiproliferative activity against human HeLa cells by sulforhodamine B assay 20973488
HeLa IC50 = 5.7 nM 8.24 Antiproliferative activity against human HeLa cells expressing tubulin 3beta by ... 20973488
SK-OV-3 IC50 = 6.6 nM 8.18 Antiproliferative activity against human SKOV3 cells expressing MDR1-6/6 by sulf... 20973488
Unchecked EC50 = 7.0 nM 8.15 Inhibition of microtubule depolymerization in rat A10 cells assessed as reorgani... 20973488
MGC-803 IC50 = 20.0 nM 7.7 Antiproliferative activity against human MGC-803 cells assessed as reduction in ... 32682200
PC-3 IC50 = 33.0 nM 7.48 Antiproliferative activity against human PC-3 cells assessed as reduction in cel... 32682200
HCT-116 IC50 = 42.0 nM 7.38 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 32682200
NON-PROTEIN TARGET IC50 = 6400.0 nM 5.19 Antiproliferative activity against human EAhy926 cells assessed as reduction in ... 27597243
NON-PROTEIN TARGET IC50 = 6400.0 nM 5.19 Antiproliferative activity against human EAhy926 cells measured after 48 hrs by ... 27592394
EA.hy 926 IC50 = 6400.0 nM 5.19 Antiproliferative activity against human EAhy926 cells after 48 hrs by MTT assay -

Literature References

PubMed DOI Target Context # Activities
20973488 10.1021/jm101010n HeLa 3
34649064 10.1016/j.ejmech.2021.113897 MHCC97H 3
20973488 10.1021/jm101010n SK-OV-3 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28217276 10.1039/C6MD00459H MCF7 2
28217276 10.1039/C6MD00459H DU-145 1
37804769 10.1016/j.ejmech.2023.115844 HCT-116 1
32682200 10.1016/j.ejmech.2020.112618 PC-3 1
32682200 10.1016/j.ejmech.2020.112618 HCT-116 1
32682200 10.1016/j.ejmech.2020.112618 MGC-803 1
28217276 10.1039/C6MD00459H Unchecked 1
28217276 10.1039/C6MD00459H NCI-H460 1
20973488 10.1021/jm101010n Unchecked 1
28217276 10.1039/C6MD00459H SK-OV-3 1
- 10.1039/C6MD00360E EA.hy 926 1
29448140 10.1016/j.ejmech.2018.02.003 Chorioallantoic membrane 1
29509413 10.1021/acs.jmedchem.8b00128 A549 1
27592394 10.1016/j.ejmech.2016.08.050 NON-PROTEIN TARGET 1
27597243 10.1016/j.bmcl.2016.08.084 NON-PROTEIN TARGET 1
27149641 10.1021/acs.jmedchem.6b00021 A549 1

Data from ChEMBL 36 via Core Engine