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Compound Detail

CHEMBL411729

CYTOCHALASIN B
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C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)/C=C/[C@H](O)CCC[C@@H](C)C/C=C/[C@H]3[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL411729
Name CYTOCHALASIN B
Phase Preclinical
Structure Type MOL
InChI Key GBOGMAARMMDZGR-TYHYBEHESA-N
15
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

479.6
MW (Da)
3.49
ALogP
5
HBA
3
HBD
95.9
PSA (Ų)
0.45
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C29H37NO5
MW 479.62
Aromatic Rings 1
Heavy Atoms 35
NP-Likeness 2.68

Activity Summary

IC50 19 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Solute carrier family 2, facilitated glucose transporter member 1
CHEMBL2535
 IC50 7.0 6.195 100.0 2
Solute carrier family 2, facilitated glucose transporter member 3
CHEMBL5215
 IC50 6.92 6.165 120.0 2
MRC5
CHEMBL614181
 IC50 6.57 6.57 270.0 1
Solute carrier family 2, facilitated glucose transporter member 4
CHEMBL5874
 IC50 6.55 5.98 280.0 2
Unchecked
CHEMBL612545
 IC50 6.37 5.475 424.0 2
SK-OV-3
CHEMBL614925
 IC50 6.34 6.34 460.0 1
SK-MEL-2
CHEMBL614917
 IC50 6.17 6.17 670.0 1
HCT-15
CHEMBL612263
 IC50 5.71 5.71 1940.0 1
A549
CHEMBL392
 IC50 5.67 5.67 2130.0 1
XF498
CHEMBL613533
 IC50 5.63 5.63 2360.0 1
Solute carrier family 2, facilitated glucose transporter member 2
CHEMBL5873
 IC50 5.55 5.55 2800.0 1
MCF7
CHEMBL387
 IC50 5.28 5.28 5200.0 1
HeLa
CHEMBL399
 IC50 5.1 5.1 7900.0 1
HepG2
CHEMBL395
 IC50 5.02 5.02 9500.0 1
HCT-116
CHEMBL394
 IC50 4.92 4.92 12000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Solute carrier family 2, facilitated glucose transporter member 1 IC50 = 100.0 nM 7.0 Inhibition of human GLUT1 expressed in human DLD-1 cells assessed as reduction i... 27552707
Solute carrier family 2, facilitated glucose transporter member 3 IC50 = 120.0 nM 6.92 Inhibition of human GLUT3 expressed in human GLUT1-/- DLD-1 cells assessed as re... 27552707
MRC5 IC50 = 270.0 nM 6.57 Cytotoxicity against human MRC5 cells assessed as inhibition of cell growth incu... 38283219
Solute carrier family 2, facilitated glucose transporter member 4 IC50 = 280.0 nM 6.55 Inhibition of human GLUT4 expressed in CHO cells assessed as reduction in glucos... 27552707
Unchecked IC50 = 423.96 nM 6.37 PUBCHEM_BIOASSAY: Luminescence-based dose response cell-based high throughput sc... -
SK-OV-3 IC50 = 460.0 nM 6.34 Cytotoxicity against human SKOV3 cells after 48 hrs by SRB assay 22483395
SK-MEL-2 IC50 = 670.0 nM 6.17 Cytotoxicity against human SK-MEL-2 cells after 48 hrs by SRB assay 22483395
HCT-15 IC50 = 1940.0 nM 5.71 Cytotoxicity against human HCT15 cells after 48 hrs by SRB assay 22483395
A549 IC50 = 2130.0 nM 5.67 Cytotoxicity against human A549 cells after 48 hrs by SRB assay 22483395
XF498 IC50 = 2360.0 nM 5.63 Cytotoxicity against human XF498 cells after 48 hrs by SRB assay 22483395
Solute carrier family 2, facilitated glucose transporter member 2 IC50 = 2800.0 nM 5.55 Inhibition of human GLUT2 expressed in CHO cells assessed as reduction in fructo... 27552707
Solute carrier family 2, facilitated glucose transporter member 4 IC50 = 3900.0 nM 5.41 Inhibition of the Glucose Transporter (GLUT4, SLC2A4) as assessed by a FRET base... -
Solute carrier family 2, facilitated glucose transporter member 3 IC50 = 3900.0 nM 5.41 Inhibition of the Glucose Transporter (GLUT3, SLC2A3) as assessed by a FRET base... -
Solute carrier family 2, facilitated glucose transporter member 1 IC50 = 4100.0 nM 5.39 Inhibition of the Glucose Transporter (GLUT1, SLC2A1) as assessed by a FRET base... -
MCF7 IC50 = 5200.0 nM 5.28 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 34846891
HeLa IC50 = 7900.0 nM 5.1 Cytotoxicity against human HeLa cells after 48 hrs by SRB assay 22483395
HepG2 IC50 = 9500.0 nM 5.02 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability a... 34846891
HCT-116 IC50 = 12000.0 nM 4.92 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 34846891
Unchecked IC50 = 26200.0 nM 4.58 Cytotoxicity against human BLM cells assessed as inhibition of cell growth incub... 38283219

Literature References

PubMed DOI Target Context # Activities
38283219 10.1039/d3md00535f Unchecked 4
18024584 10.1073/pnas.0709695104 H4 4
36413818 10.1016/j.ejmech.2022.114904 Unchecked 4
33341499 10.1016/j.bmc.2020.115928 MDA-MB-231 4
22483395 10.1016/j.bmcl.2012.03.058 HeLa 3
15165136 10.1021/np030524n Unchecked 3
32404031 10.1161/circresaha.119.316463 Unchecked 3
7852999 10.1021/np50113a004 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
8988604 10.1021/np960144k C6 2
15165136 10.1021/np030524n Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 2
11374943 10.1021/np000436s Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 2
33341499 10.1016/j.bmc.2020.115928 Unchecked 2
15165136 10.1021/np030524n RAW264.7 2
12880315 10.1021/np030086k Integrin alpha-L 2
11374943 10.1021/np000436s Unchecked 2
12880315 10.1021/np030086k Unchecked 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] B 2
28098449 10.1021/acs.jmedchem.6b01134 Unchecked 2
15165136 10.1021/np030524n HL-60 1

Data from ChEMBL 36 via Core Engine