Structure

InChI Key KDQAABAKXDWYSZ-PNYVAJAMSA-N
Smiles CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1.O=S(=O)(O)O
InChI
InChI=1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C46H60N4O13S
Molecular Weight 909.07
AlogP 3.99
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 154.1
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 59.0

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR DailyMed Wikipedia
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(%)
Enzyme Hydrolase
- - - - 0
Structural protein
- 130-130 - - -
Assay Description Organism Bioactivity Reference
In vitro concentration required to kill 50% of COLO 320 human colorectal carcinoma cell line Homo sapiens 80.0 nM
In vitro concentration required to kill 50% of LNCaP human prostate cancer cell line Homo sapiens 500.0 nM
In vitro inhibitory concentration against human chronic myelogenous leukemia K562 cell growth Homo sapiens 1.0 nM
In vitro inhibition of maximum porcine tubulin assembly rate after 20 min at 37 degrees C Sus scrofa 130.0 nM
In vitro concentration required to kill 50% of T47D human breast ductal carcinoma cell line Homo sapiens 80.0 nM
Antiproliferative activity against human K562 cell line Homo sapiens 1.0 nM
Inhibition of tubulin polymerization in porcine brain Sus scrofa 130.0 nM
Antiproliferative activity against human K562 cells after 48 hrs Homo sapiens 1.0 nM
Inhibition of porcine brain tubulin polymerization Sus scrofa 130.0 nM
Antiproliferative activity against human K562 cells after 48 hrs Homo sapiens 1.0 nM
Inhibition of pig brain tubulin polymerization after 30 mins by turbidimetric assay Sus scrofa 130.0 nM
Cytotoxicity against human A549 cells Homo sapiens 0.002 ug.mL-1
Cytotoxicity against human HCT8 cells Homo sapiens 0.005 ug.mL-1
Antiproliferative activity against human K562 cells after 48 hrs Homo sapiens 1.0 nM
Inhibition of pig brain tubulin polymerization after 30 mins by turbidimetry Sus scrofa 130.0 nM
Cell growth inhibition of human K562 cells after 48 hrs Homo sapiens 1.0 nM
Inhibition of tubulin polymerization in human K562 cells Homo sapiens 130.0 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 0.52 nM Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 398.11 nM
Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 1.05 nM
Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR green assay Plasmodium falciparum D10 1.05 nM
Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR green assay Plasmodium falciparum 0.93 nM Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR green assay Plasmodium falciparum 398.11 nM
Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR green assay Plasmodium falciparum 0.93 nM
Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 1.0 nM
Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 0.32 nM Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 398.11 nM
Antiproliferative activity against human K562 cells after 48 hrs by hemocytometric analysis Homo sapiens 1.0 nM
Inhibition of pig tubulin polymerization determined after 45 mins at 37 degC by turbidimetric analysis Sus scrofa 130.0 nM
Antiproliferative activity against human K562 cells after 48 hrs by hemocytometer Homo sapiens 1.0 nM
Inhibition of pig brain tubulin polymerization after 30 mins by turbidimetry analysis Sus scrofa 130.0 nM
Cytotoxicity against human HT-29 cells after 48 hrs by MTS assay Homo sapiens 550.0 nM
Inhibition of bovine brain tubulin polymerization at 10 uM after 1 hrs by fluorescence assay Bos taurus 66.0 %
Antiproliferative activity against human HepG2 cells after 48 hrs by MTS assay Homo sapiens 160.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 15.44 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 0.36 %
Cytotoxicity against adriamycin-resistant human HepG2 cells assessed as growth inhibition after 72 hrs by MTT assay Homo sapiens 56.0 nM
Cytotoxicity against human HepG2 cells assessed as growth inhibition after 72 hrs by MTT assay Homo sapiens 19.0 nM
Cytotoxicity against human K562 cells assessed as growth inhibition after 72 hrs by MTT assay Homo sapiens 16.0 nM
Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by MTT assay Homo sapiens 8.3 nM
Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs by MTT assay Homo sapiens 7.0 nM
PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 5.8 nM PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 3.5 nM
PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of assay: confirmatory) None 4.8 nM PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of assay: confirmatory) None 3.3 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory) None 5.21 nM PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory) None 2.6 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 2.6 nM PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 2.3 nM
PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of assay: confirmatory) None 3.2 nM PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of assay: confirmatory) None 4.83 nM
PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 8.9 nM
PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. Increased chromatin condensation in HeLa cells-IC50. (Class of assay: confirmatory) None 3.2 nM PubChem BioAssay. Increased chromatin condensation in HeLa cells-IC50. (Class of assay: confirmatory) None 4.52 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 33.96 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -11.69 %
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 2.76 % 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 2.76 %

Cross References

Resources Reference
ChEMBL CHEMBL378544
FDA SRS N00W22YO2B
Guide to Pharmacology 6851
PDB VLB
PubChem 5388983
SureChEMBL SCHEMBL3549
ZINC ZINC85432544