EPOTHILONE D

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII T0358E0YUF
EPA CompTox DTXSID70880053

Structure

InChI Key XOZIUKBZLSUILX-GIQCAXHBSA-N
Smiles C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1
InChI
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H41NO5S
Molecular Weight 491.69
AlogP 5.27
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 96.72
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 34.0

Bioactivity

Mechanism of Action Action Reference
Tubulin stabiliser STABILISER PubMed PubMed PubMed PubMed
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(%)
Structural protein
- - - - 43
Assay Description Organism Bioactivity Reference
Concentration required to inhibit the growth of paclitaxel-sensitive human epidermoid carcinoma cells KB-31 by 50 percent (72 hr exposure) Homo sapiens 2.7 nM
Concentration required to inhibit the growth of paclitaxel-resistant human epidermoid carcinoma cells KB-8511 by 50 percent (72 hr exposure) Homo sapiens 1.44 nM
Concentrations required to induce 50 percent polymerization of porcine brain-derived micro-tubule protein Sus scrofa 880.0 nM
Cytotoxicity against human MCF7 cells after 3 days by SRB assay Homo sapiens 16.0 nM
Cytotoxicity against human NCI/ADR cells after 3 days by SRB assay Homo sapiens 44.0 nM
Cytotoxicity against human SF268 cells after 3 days by SRB assay Homo sapiens 18.0 nM
Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay Homo sapiens 30.0 nM
Cytotoxicity against mouse L929 cells Mus musculus 0.02 ug.mL-1
Cytotoxicity against human MCF7 cells after 3 days by SRB assay Homo sapiens 8.0 nM
Cytotoxicity against human NCI/ADR-RES cells after 3 days by SRB assay Homo sapiens 30.0 nM
Cytotoxicity against human SF268 cells after 3 days by SRB assay Homo sapiens 14.0 nM
Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay Homo sapiens 8.0 nM
Cytotoxicity against human HL60 cells after 3 days by SRB assay Homo sapiens 8.0 nM
Cytotoxicity against mitoxantrone-resistant human HL60 cells after 3 days by SRB assay Homo sapiens 10.0 nM
Cytotoxicity against human CCRF-CEM cells after 3 days by SRB assay Homo sapiens 22.0 nM
Cytotoxicity against camptothecin-resistant human CCRF-CEM cells after 3 days by SRB assay Homo sapiens 15.0 nM
Inhibition of tubulin polymerization (unknown origin) at 5 uM Homo sapiens 43.3 %
Cytotoxicity against human MCF7 cells after 72 hrs Homo sapiens 14.0 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 2.11 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.083 %
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 -0.06 % 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 -0.06 %

Related Entries

Cross References

Resources Reference
ChEBI 29579
ChEMBL CHEMBL96172
DrugBank DB01873
FDA SRS T0358E0YUF
KEGG C12039
PDB EPD
PubChem 447865
SureChEMBL SCHEMBL4415
ZINC ZINC000003951739
CONTENTS