PENTOSTATIN

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Search structure


Trade Names	NIPENT PENTOSTATIN
Synonyms	CI-825 Deoxycoformycin NSC-218321 Nipent PD 81565 PD-81565 Pentostatin YK-176
Status
Molecule Category	UNKNOWN
ATC	L01XX08
UNII	395575MZO7
EPA CompTox	DTXSID2023436


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

Structure


InChI Key	FPVKHBSQESCIEP-JQCXWYLXSA-N
Smiles	OC[C@H]1O[C@@H](n2cnc3c2N=CNC[C@H]3O)C[C@@H]1O
InChI	InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C11H16N4O4
Molecular Weight	268.27
AlogP	-1.18
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	2.0
Polar Surface Area	112.13
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	19.0

Bioactivity

Mechanism of Action	Action	Reference
Adenosine deaminase inhibitor	INHIBITOR	DailyMed


Protein: Adenosine deaminase Description: Adenosine deaminase Organism : Homo sapiens P00813 ENSG00000196839

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	-	-	0-1	-

Assay Description	Organism	Bioactivity	Reference
Binding affinity (Ki) at calf intestinal adenosine deaminase.	None	0.0025 nM
Binding affinity against Adenosine deaminase from calf intestinal mucosa was determined	None	0.01 nM
Binding affinity towards calf spleen adenosine deaminase was determined	None	0.001 nM
Compound was tested for the inhibition of adenosine deaminase from calf intestine; Range of 0.01-0.001 nM	None	0.001 nM
Compound was evaluated for the inhibition of adenosine deaminase	None	0.1 nM
Inhibition constant against human adenosine deaminase was determined	None	0.033 nM
The compound was tested in vitro for inhibition of human erythrocytic adenosine deaminase.	None	0.0025 nM
Compound was evaluated for the cytotoxicity against L1210 cells in presence of coformycin	Mus musculus	250.0 nM
Inhibition of adenosine deaminase	None	0.0001 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	3.17 %
Inhibition of human erythrocytes ADA assessed as reduction in formation of inosine using adenosine as substrate	Homo sapiens	0.5 nM
Inhibition of human erythrocytes ADA assessed as equilibrium dissociation constant by measuring reduction in formation of inosine using adenosine as substrate	Homo sapiens	0.026 nM
Inhibition of Plasmodium falciparum N-terminal thrombin cleavable His6-tagged ADA expressed in Escherichia coli BL21 assessed as reduction in formation of inosine using adenosine as substrate	Plasmodium falciparum	8.2 nM
Inhibition of Plasmodium falciparum N-terminal thrombin cleavable His6-tagged ADA expressed in Escherichia coli BL21 assessed as equilibrium dissociation constant by measuring reduction in formation of inosine using adenosine as substrate	Plasmodium falciparum	0.038 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	10.69 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.02 %
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	-0.02 %		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	-0.07 %		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	-0.02 %		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	-0.07 %

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL1580
DrugBank	DB00552
DrugCentral	2098
FDA SRS	395575MZO7
Human Metabolome Database	HMDB0014692
Guide to Pharmacology	4805
KEGG	C02267
PDB	DCF
PharmGKB	PA450863
PubChem	439693
SureChEMBL	SCHEMBL2817
ZINC	ZINC000003806262

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).