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Compound Detail

CHEMBL339231

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CO[C@H]1/C=C\C=C(/C)C(=O)NC2=CC(=O)C(N)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(N)=O)C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL339231
Phase Preclinical
Structure Type MOL
InChI Key XYFFWTYOFPSZRM-TWNAANEASA-N
5
Targets
16
Activities
4
Assay Types
18
PK Parameters
18
Publications
0
Known Names

Molecular Properties

545.6
MW (Da)
1.72
ALogP
9
HBA
4
HBD
180.3
PSA (Ų)
0.30
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H39N3O8
MW 545.63
Aromatic Rings 0
Heavy Atoms 39
NP-Likeness 2.57

Activity Summary

EC50 6 meas. best 8.22
IC50 6 meas. best 8.15
Kd 2 meas. best 7.0
Ki 2 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Heat shock protein HSP 90-beta
CHEMBL4303
 Ki 8.52 8.1 3.0 2
Heat shock protein HSP90
CHEMBL2095165
 EC50 8.22 7.768 6.0 5
Heat shock protein HSP 90-beta
CHEMBL4303
 IC50 8.15 8.035 7.0 2
SK-BR-3
CHEMBL613834
 IC50 7.48 7.455 33.0 4
Endoplasmin
CHEMBL4748
 EC50 7.32 7.32 48.0 1
Heat shock protein HSP 90-alpha
CHEMBL3880
 Kd 7.0 7.0 100.0 1
Heat shock protein HSP 90-beta
CHEMBL4303
 Kd 7.0 7.0 100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8184.45 ng.hr.mL-1 Mus musculus
AUC 23462.09 ng.hr.mL-1 Mus musculus
AUC 32192.17 ng.hr.mL-1 Mus musculus
AUC 11458.23 ng.hr.mL-1 Homo sapiens
CL 0.11 L/hr Mus musculus
CL 0.03 L/hr Mus musculus
CL 0.02 L/hr Mus musculus
Cmax 4800.0 nM Mus musculus
Cmax 18000.0 nM Mus musculus
Cmax 3000.0 nM Homo sapiens
T1/2 1.2 hr Mus musculus
T1/2 13.7 hr Mus musculus
T1/2 1.8 hr Mus musculus
T1/2 6.9 hr Homo sapiens
Tmax 1.7 hr Homo sapiens
Vz 0.18 l Mus musculus
Vz 0.49 l Mus musculus
Vz 0.06 l Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Heat shock protein HSP 90-beta Ki = 3.0 nM 8.52 Binding affinity to HSP90 under reducing conditions in presence of TECP 20055425
Heat shock protein HSP90 EC50 = 6.0 nM 8.22 Upregulation of Hsp70 in SKOV3 cells 16854066
Heat shock protein HSP 90-beta IC50 = 7.0 nM 8.15 Inhibition of HSP90-mediated client protein HER2 degradation 20055425
Heat shock protein HSP90 EC50 = 8.0 nM 8.1 Degradation of Her2 in SKBR3 cells 16854066
Heat shock protein HSP 90-beta IC50 = 12.0 nM 7.92 Inhibition of HSP90-mediated client protein HER2 degradation in human MCF7 cells 20055425
Heat shock protein HSP90 EC50 = 17.0 nM 7.77 Upregulation of Hsp70 in SKBR3 cells 16854066
Heat shock protein HSP 90-beta Ki = 21.0 nM 7.68 Binding affinity to HSP90 under non-reducing conditions in absence of TECP 20055425
SK-BR-3 IC50 = 33.0 nM 7.48 Cytotoxicity against SKBr3 cells 16165354
SK-BR-3 IC50 = 33.0 nM 7.48 Cytotoxicity against human SKBR3 cells after 72 hrs by celltiter-glo assay 19405528
Heat shock protein HSP90 EC50 = 34.0 nM 7.47 Inhibition of BODIPY-AG binding to human HSP90 16854066
SK-BR-3 IC50 = 37.0 nM 7.43 Inhibition of oncogene product p185 erbB-2 from human breast cancer cells(SK-BR-... 7562911
SK-BR-3 IC50 = 37.0 nM 7.43 In vitro inhibition of p185 erbB-2 oncoprotein in human breast cancer SK-BR-3 ce... 7562912
Endoplasmin EC50 = 48.0 nM 7.32 Inhibition of BODIPY-AG binding to dog Grp94 16854066
Heat shock protein HSP90 EC50 = 53.0 nM 7.28 Degradation of Her2 in SKOV3 cells 16854066
Heat shock protein HSP 90-alpha Kd = 100.0 nM 7.0 Binding affinity for human heat shock protein 90 in scintillation proximity assa... 16165354
Heat shock protein HSP 90-beta Kd = 100.0 nM 7.0 Binding affinity to human recombinant HSP90 19405528

Literature References

PubMed DOI Target Context # Activities
20055425 10.1021/jm9004708 Homo sapiens 5
20055425 10.1021/jm9004708 Liver 5
20055425 10.1021/jm9004708 ADMET 5
16854066 10.1021/jm0603116 Heat shock protein HSP90 5
20055425 10.1021/jm9004708 Plasma 5
17034135 10.1021/jm060647f LS174T 4
20055425 10.1021/jm9004708 Heat shock protein HSP 90-beta 4
7562911 10.1021/jm00019a010 SK-BR-3 3
16854066 10.1021/jm0603116 SK-BR-3 1
16854066 10.1021/jm0603116 Endoplasmin 1
17442565 10.1016/j.bmcl.2006.12.041 Molecular identity unknown 1
19405528 10.1021/jm900098v SK-BR-3 1
19405528 10.1021/jm900098v Heat shock protein HSP 90-beta 1
16854066 10.1021/jm0603116 SK-OV-3 1
16165354 10.1016/j.bmcl.2005.08.013 SK-BR-3 1
16165354 10.1016/j.bmcl.2005.08.013 Heat shock protein HSP 90-alpha 1
7562912 10.1021/jm00019a011 Mus musculus 1
7562912 10.1021/jm00019a011 SK-BR-3 1

Data from ChEMBL 36 via Core Engine