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Compound Detail

CHEMBL583969

PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER
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Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL583969
Name PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER
Phase Preclinical
Structure Type MOL
InChI Key OLCWZBFDIYXLAA-IOSLPCCCSA-N
7
Targets
35
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

425.2
MW (Da)
-1.64
ALogP
11
HBA
6
HBD
223.4
PSA (Ų)
0.29
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H17N5O9P2
MW 425.23
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.98

Activity Summary

Ki 18 meas. best 7.05
IC50 15 meas. best 7.3
EC50 1 meas. best 4.79
Kd 1 meas. best 4.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5'-nucleotidase
CHEMBL5957
 IC50 7.3 5.76 50.0 12
5'-nucleotidase
CHEMBL5957
 Ki 7.05 6.9088 88.4 8
5'-nucleotidase
CHEMBL1075214
 Ki 6.78 6.5167 167.0 3
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
CHEMBL5925
 Ki 5.89 4.9917 1280.0 6
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1
CHEMBL3964
 IC50 5.66 5.66 2198.0 1
5'-nucleotidase
CHEMBL4680034
 IC50 5.33 5.33 4630.0 2
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
CHEMBL4295913
 Ki 5.02 5.02 9600.0 1
5'-nucleotidase
CHEMBL5957
 EC50 4.79 4.79 16268.0 1
Unchecked
CHEMBL612545
 Kd 4.57 4.57 27000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5'-nucleotidase IC50 = 50.0 nM 7.3 Inhibition of human CD73 expressed in CHO cells using AMP as substrate preincuba... 32786396
5'-nucleotidase IC50 = 60.0 nM 7.22 Inhibition of human C-terminal His6-tagged CD73 expressed in HEK293F cells using... 32786396
5'-nucleotidase Ki = 88.4 nM 7.05 Inhibition of purified recombinant soluble human CD73 expressed in Sf9 cells [3H... 32045236
5'-nucleotidase Ki = 88.4 nM 7.05 Binding affinity to human recombinant CD73 (29 to 549 residues) expressed in Esc... 38086190
5'-nucleotidase Ki = 88.4 nM 7.05 Inhibition of CD73 (unknown origin) 35217359
5'-nucleotidase Ki = 88.4 nM 7.05 Inhibition of human recombinant soluble CD73 assessed as inhibition constant by ... 35080883
5'-nucleotidase Ki = 88.4 nM 7.05 Inhibition of human CD73 using AMP as substrate by Malachite green phosphate rea... 32614585
5'-nucleotidase Ki = 88.4 nM 7.05 Inhibition of human CD73 32212732
5'-nucleotidase Ki = 167.0 nM 6.78 Inhibition of recombinant rat C-terminal His-tagged soluble form of CD73 express... 30895781
5'-nucleotidase IC50 = 187.0 nM 6.73 Inhibition of human CD73 using AMP as substrate by Malachite green phosphate rea... 32614585
5'-nucleotidase Ki = 197.0 nM 6.71 Inhibition of purified recombinant soluble rat CD73 expressed in Sf9 cells [3H]A... 32045236
5'-nucleotidase Ki = 207.0 nM 6.68 Inhibition of native CD73 in human MDA-MB-231 cell membrane preparations [3H]AMP... 32045236
5'-nucleotidase Ki = 510.0 nM 6.29 Inhibition of CD73 in human melanoma 1539 cells using AMP substrate by capillary... 32786396
5'-nucleotidase Ki = 870.0 nM 6.06 Inhibition of rat CD73 expressed in baculovirus infected insect cells using AMP ... 32786396
5'-nucleotidase IC50 = 1100.0 nM 5.96 Inhibition of recombinant human CD73 using AMP as substrate incubated for 90 min... 32786396
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 1280.0 nM 5.89 Competitive-inhibition of recombinant human N-terminal His-tagged soluble NPP1 (... 30108800
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 IC50 = 2198.0 nM 5.66 PubChem BioAssay. Counterscreen for inhibitors of phospholipase C isozymes (PLC-... -
5'-nucleotidase IC50 = 2500.0 nM 5.6 Inhibition of recombinant human CD73 using AMP as substrate incubated for 120 mi... 32786396
5'-nucleotidase IC50 = 2653.0 nM 5.58 Inhibition of human C-terminal His6-tagged CD73 expressed in CHO cells preincuba... 32865411
5'-nucleotidase IC50 = 3800.0 nM 5.42 Inhibition of recombinant CD73 (27 to 549 residues) (unknown origin) expressed i... 30176535

Literature References

PubMed DOI Target Context # Activities
30108800 10.1039/C7MD00015D Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 6
32786396 10.1021/acs.jmedchem.0c01044 5'-nucleotidase 6
30895781 10.1021/acs.jmedchem.9b00164 5'-nucleotidase 3
32045236 10.1021/acs.jmedchem.9b01611 5'-nucleotidase 3
35217359 10.1016/j.bmc.2022.116672 5'-nucleotidase 3
35080883 10.1021/acs.jmedchem.1c01852 5'-nucleotidase 3
30176535 10.1016/j.ejmech.2018.08.035 5'-nucleotidase 3
33359608 10.1016/j.bmcl.2020.127758 5'-nucleotidase 2
32865411 10.1021/acs.jmedchem.0c01086 5'-nucleotidase 2
32614585 10.1021/acs.jmedchem.0c00525 5'-nucleotidase 2
32045236 10.1021/acs.jmedchem.9b01611 ADMET 2
19678707 10.1021/jm900728u Unchecked 1
32212732 10.1021/acs.jmedchem.9b01713 5'-nucleotidase 1
33359608 10.1016/j.bmcl.2020.127758 Ectonucleoside triphosphate diphosphohydrolase 1 1
32045236 10.1021/acs.jmedchem.9b01611 P2Y purinoceptor 12 1
32045236 10.1021/acs.jmedchem.9b01611 P2Y purinoceptor 1 1
35217359 10.1016/j.bmc.2022.116672 Unchecked 1
36529947 10.1021/acs.jmedchem.2c01287 5'-nucleotidase 1
38359537 10.1016/j.ejmech.2024.116211 Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 1
38086190 10.1016/j.ejmech.2023.116028 5'-nucleotidase 1

Data from ChEMBL 36 via Core Engine