ISPINESIB

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Search structure


Synonyms	Ispinesib
Status
Molecule Category	UNKNOWN
UNII	BKT5F9C2NI
EPA CompTox	DTXSID20187307


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	QJZRFPJCWMNVAV-HHHXNRCGSA-N
Smiles	Cc1ccc(C(=O)N(CCCN)[C@@H](c2nc3cc(Cl)ccc3c(=O)n2Cc2ccccc2)C(C)C)cc1
InChI	InChI=1S/C30H33ClN4O2/c1-20(2)27(34(17-7-16-32)29(36)23-12-10-21(3)11-13-23)28-33-26-18-24(31)14-15-25(26)30(37)35(28)19-22-8-5-4-6-9-22/h4-6,8-15,18,20,27H,7,16-17,19,32H2,1-3H3/t27-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C30H33ClN4O2
Molecular Weight	517.07
AlogP	5.59
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	9.0
Polar Surface Area	81.22
Molecular species	BASE
Aromatic Rings	4.0
Heavy Atoms	37.0

Bioactivity

Mechanism of Action	Action	Reference
Kinesin-like protein 1 inhibitor	INHIBITOR	PubMed Other

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19	-	24300	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	4100	-	-	-
Enzyme Hydrolase	-	-	-	-	4
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	4810	-	-	-
Other cytosolic protein	-	5-47	-	2-3	100
Unclassified protein	-	-	-	-	7

Assay Description	Organism	Bioactivity	Reference
Inhibition of CENPE at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	7.0 %
Inhibition of Kif1A at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	8.2 %
Inhibition of MKLP1 at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	7.1 %
Inhibition of RabK6 at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	11.0 %
Inhibition of HSET at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	4.2 %
Inhibition of MCAK at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	8.2 %
Inhibition of Kif4 at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	4.3 %
Inhibition of Eg5 at 10 uM by puruvate kinsase-lactate dehydrogenase detection system	None	99.6 %
Inhibition of N-terminal hexa-histidine tagged human cloned Eg5 (1 to 368 amino acids) expressed in Escherichia coli BL21 (DE3) assessed as reduction of MT-stimulated ATPase activity by pyruvate kinase/lactate dehydrogenase-linked assay	Homo sapiens	2.5 nM
Inhibition of MT-stimulated human N-terminal His6-tagged Eg5 (1 to 368 amino acid residues) motor domain ATPase activity expressed in Escherichia coli BL21 (DE3) by pyruvate kinase/lactate dehydrogenase-coupled assay	Homo sapiens	2.3 nM
Inhibition of C-terminal His-tagged microtubule-stimulated KSP motor domain (1 to 369) ATPase activity (unknown origin) preincubated for 30 mins followed by ATP addition measured after 15 mins by luciferase-derived luminescence assay	Homo sapiens	5.0 nM
Inhibition of His-tagged KSP motor domain (1 to 369) (unknown origin) assessed as inhibition of microtubule-stimulated KSP ATPase activity preincuabted for 30 mins followed by ATP addition measured after 15 mins by Kinase-Glo assay	Homo sapiens	47.0 nM
Growth inhibition of human HCT116 cells after 72 hrs by MTS assay	Homo sapiens	1.1 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	91.86 %
Inhibition of Kinesin Eg5 (unknown origin)	Homo sapiens	2.3 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	10.79 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	1.536 %
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	-0.29 %		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	-0.3 %		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	-0.3 %		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	-0.29 %
Antischistosomal activity against Schistosoma mansoni Liberian NTS incubated for 72 hrs by microscopic method	Schistosoma mansoni	900.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	94692
ChEMBL	CHEMBL228814
DrugBank	DB06188
FDA SRS	BKT5F9C2NI
PDB	G7X
PubChem	6851740
SureChEMBL	SCHEMBL3582165
ZINC	ZINC000011680799

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).