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Compound Detail

CHEMBL364447

DISERMOLIDE
🧪 Phase II
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🧪 Phase II
C=C/C=C\[C@H](C)[C@H](OC(N)=O)[C@@H](C)[C@H](O)[C@@H](C)C/C(C)=C\[C@H](C)[C@@H](O)[C@@H](C)/C=C\[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL364447
Name DISERMOLIDE
Phase Phase II
Structure Type MOL
InChI Key AADVCYNFEREWOS-OBRABYBLSA-N

Known Names

Discodermolide Disermolida Disermolide XAA 296 XAA-296 XAA296
13
Targets
35
Activities
2
Assay Types
2
PK Parameters
20
Publications
6
Known Names

Molecular Properties

593.8
MW (Da)
4.30
ALogP
8
HBA
5
HBD
159.5
PSA (Ų)
0.10
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C33H55NO8
MW 593.80
Aromatic Rings 0
Heavy Atoms 42
NP-Likeness 2.66

Activity Summary

IC50 34 meas. best 8.74
Kd 1 meas. best 9.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 9.74 9.74 0.2 1
A549
CHEMBL392
 IC50 8.74 7.9983 1.8 6
MCF7
CHEMBL387
 IC50 8.62 8.09 2.4 3
SK-OV-3
CHEMBL614925
 IC50 8.21 7.945 6.1 2
ADMET
CHEMBL612558
 IC50 8.0 7.5 10.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.77 7.285 17.0 2
DLD-1
CHEMBL614285
 IC50 7.54 7.54 29.0 3
P388
CHEMBL389
 IC50 7.48 7.464 33.0 5
PANC-1
CHEMBL614139
 IC50 7.31 7.25 49.0 4
ASPC1
CHEMBL612588
 IC50 7.01 7.01 98.0 3
NCI/ADR-RES
CHEMBL613829
 IC50 6.8 6.8 160.0 1
NCI
CHEMBL614877
 IC50 6.8 6.8 160.0 1
Unchecked
CHEMBL612545
 IC50 6.24 6.24 580.0 1
Vero
CHEMBL391
 IC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 260.68 ng.hr.mL-1 Mus musculus
AUC 66.51 ng.hr.mL-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 0.18 nM 9.74 Binding affinity to microtubule 17206139
A549 IC50 = 1.8 nM 8.74 Antiproliferative activity against human A549 cells assessed as cell growth inhi... 33038665
MCF7 IC50 = 2.4 nM 8.62 Cytotoxicity against human MCF7 cells 15165132
SK-OV-3 IC50 = 6.1 nM 8.21 Antiproliferative activity against human SK-OV-3 cells assessed as cell growth i... 33038665
MCF7 IC50 = 7.98 nM 8.1 Antiproliferative activity against human MCF7 cells after 96 hrs by SRB method 21870795
A549 IC50 = 9.34 nM 8.03 Antiproliferative activity against human A549 cells after 72 hrs by SRB method 21870795
ADMET IC50 = 10.0 nM 8.0 Inhibitory concentration of compound required for exhibiting cytotoxic effect on... 15837302
A549 IC50 = 13.5 nM 7.87 Cytotoxicity against human A549 cells 12444691
A549 IC50 = 13.5 nM 7.87 Cytotoxicity against human A549 cells 12502323
A549 IC50 = 15.0 nM 7.82 Cytotoxicity against human A549 cells 15165132
NON-PROTEIN TARGET IC50 = 17.0 nM 7.77 Cytotoxicity against human NCI/ADR cells 15165132
SK-OV-3 IC50 = 21.0 nM 7.68 Inhibitory concentration (toxicity at 10-20 mg/kg dose) exhibited against SKOV3 ... 15979874
A549 IC50 = 22.0 nM 7.66 Inhibitory concentration (toxicity at 10-20 mg/kg dose) exhibited against A549 c... 15979874
MCF7 IC50 = 28.0 nM 7.55 Inhibitory concentration (toxicity at 10-20 mg/kg dose) exhibited against MCF-7 ... 15979874
DLD-1 IC50 = 29.0 nM 7.54 Cytotoxicity against taxol-sensitive human DLD1 cells after 72 hrs by MTT assay 18951787
DLD-1 IC50 = 29.0 nM 7.54 Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay 17336522
DLD-1 IC50 = 29.0 nM 7.54 Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay 18081257
P388 IC50 = 33.0 nM 7.48 Cytotoxicity against mouse P388 cells 15165132
P388 IC50 = 35.0 nM 7.46 Cytotoxicity against mouse P388 cells by MTT assay 18081257
P388 IC50 = 35.0 nM 7.46 Cytotoxicity against mouse P388 cells after 48 hrs by MTT assay 12444691

Literature References

PubMed DOI Target Context # Activities
19775091 10.1021/np900245k Liver microsomes 4
29522336 10.1021/acs.jnatprod.8b00111 MDA-MB-468 4
16413186 10.1016/j.bmcl.2005.12.066 CCRF-CEM 4
29522336 10.1021/acs.jnatprod.8b00111 Hs-578T 3
20014752 10.1021/tx900326k Hepatotoxicity 3
17206139 10.1038/nchembio853 Unchecked 3
17542572 10.1021/jm061385k Unchecked 2
16413186 10.1016/j.bmcl.2005.12.066 A549 2
29522336 10.1021/acs.jnatprod.8b00111 HEY 2
15837302 10.1016/j.bmcl.2005.03.018 ADMET 2
28675836 10.1016/j.ejmech.2017.06.047 Unchecked 2
16539395 10.1021/jm051030l 2008 1
33038665 10.1016/j.bmc.2020.115792 SK-OV-3 1
16539395 10.1021/jm051030l PC-3 1
16539395 10.1021/jm051030l HT-29 1
16539395 10.1021/jm051030l MDA-MB-231 1
15979874 10.1016/j.bmcl.2005.05.068 SK-OV-3 1
15979874 10.1016/j.bmcl.2005.05.068 A549 1
12825928 10.1021/jm0204136 Unchecked 1
12825928 10.1021/jm0204136 PC-3 1

Data from ChEMBL 36 via Core Engine