IXABEPILONE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC L01DC04
UNII K27005NP0A
EPA CompTox DTXSID70870252

Structure

InChI Key FABUFPQFXZVHFB-PVYNADRNSA-N
Smiles C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1
InChI
InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H42N2O5S
Molecular Weight 506.71
AlogP 4.05
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 112.05
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 35.0

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR PubMed DailyMed
Protein: Tubulin
Description: Tubulin beta-4A chain
Organism : Homo sapiens
P04350 ENSG00000104833
Protein: Tubulin
Description: Tubulin beta chain
Organism : Homo sapiens
P07437 ENSG00000196230
Protein: Tubulin
Description: Tubulin alpha-3C chain
Organism : Homo sapiens
P0DPH7 ENSG00000198033
Protein: Tubulin
Description: Tubulin alpha-1B chain
Organism : Homo sapiens
P68363 ENSG00000123416
Protein: Tubulin
Description: Tubulin alpha-4A chain
Organism : Homo sapiens
P68366 ENSG00000127824
Protein: Tubulin
Description: Tubulin beta-4B chain
Organism : Homo sapiens
P68371 ENSG00000188229
Protein: Tubulin
Description: Tubulin beta-3 chain
Organism : Homo sapiens
Q13509 ENSG00000258947
Protein: Tubulin
Description: Tubulin beta-2A chain
Organism : Homo sapiens
Q13885 ENSG00000137267
Protein: Tubulin
Description: Tubulin beta-8 chain
Organism : Homo sapiens
Q3ZCM7 ENSG00000261456
Protein: Tubulin
Description: Tubulin alpha-3E chain
Organism : Homo sapiens
Q6PEY2 ENSG00000152086
Protein: Tubulin
Description: Tubulin alpha-1A chain
Organism : Homo sapiens
Q71U36 ENSG00000167552
Protein: Tubulin
Description: Tubulin alpha-1C chain
Organism : Homo sapiens
Q9BQE3 ENSG00000167553
Protein: Tubulin
Description: Tubulin beta-6 chain
Organism : Homo sapiens
Q9BUF5 ENSG00000176014
Protein: Tubulin
Description: Tubulin beta-2B chain
Organism : Homo sapiens
Q9BVA1 ENSG00000137285
Protein: Tubulin
Description: Tubulin beta-1 chain
Organism : Homo sapiens
Q9H4B7 ENSG00000101162
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Other ion channel Miscellaneous ion channel Bcl-2 family
- - 337 - -
Assay Description Organism Bioactivity Reference
Cytotoxicity against human 1A9 cells Homo sapiens 6.65 nM
Cytotoxicity against human HCT116 cells Homo sapiens 2.6 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -6.52 %
Antiproliferative activity against human KB cells assessed as reduction in cell viability after 72 hrs by MTS assay Homo sapiens 8.0 nM
Antiproliferative activity against human CCRF-CEM cells assessed as reduction in cell viability after 72 hrs by MTS assay Homo sapiens 3.0 nM
Antiproliferative activity against human KBtax cells assessed as reduction in cell viability after 72 hrs by MTS assay Homo sapiens 35.0 nM
Antiproliferative activity against human KB/VCR cells assessed as reduction in cell viability after 72 hrs by MTS assay Homo sapiens 193.0 nM
Antiproliferative activity against human CCRF-CEM/VBL cells assessed as reduction in cell viability after 72 hrs by MTS assay Homo sapiens 150.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.4 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.18 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.18 %
Binding affinity to human recombinant Bcl-2 expressed in Escherichia coli by Surface plasmon resonance assay Homo sapiens 337.0 nM

Cross References

Resources Reference
ChEBI 63605
ChEMBL CHEMBL1201752
DrugBank DB04845
DrugCentral 1517
FDA SRS K27005NP0A
Guide to Pharmacology 6824
PDB GZX
PubChem 6445540
SureChEMBL SCHEMBL8386
ZINC ZINC000003993846
CONTENTS