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Compound Detail

CHEMBL132722

DIPHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER
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Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O

Basic Information

ChEMBL ID CHEMBL132722
Name DIPHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER
Phase Preclinical
Structure Type MOL
InChI Key CAWZRIXWFRFUQB-IOSLPCCCSA-N
7
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

505.2
MW (Da)
-1.52
ALogP
13
HBA
7
HBD
269.9
PSA (Ų)
0.20
QED
3
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H18N5O12P3
MW 505.21
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 1.02

Activity Summary

Ki 11 meas. best 9.01
IC50 7 meas. best 8.72
EC50 4 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.01 8.36 1.0 3
Unchecked
CHEMBL612545
IC50 8.72 8.2171 1.9 7
P2X purinoceptor 1
CHEMBL2094
EC50 6.7 6.7 200.0 1
P2X purinoceptor 3
CHEMBL2998
EC50 6.13 6.13 740.0 1
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
CHEMBL4295913
Ki 5.66 5.66 2200.0 1
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
CHEMBL5925
Ki 5.48 5.066 3320.0 5
P2X purinoceptor 4
CHEMBL2818
EC50 4.48 4.48 33000.0 1
P2X purinoceptor 2
CHEMBL2135
EC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.97 nM 9.01 Binding affinity to P2X receptor (unknown origin) by radioligand displacement as... 23466604
Unchecked IC50 = 1.9 nM 8.72 Displacement of [3H]alpha,beta-MeATP from rat urinary bladder P2X receptor 26988801
Unchecked IC50 = 1.9 nM 8.72 Displacement of [3H]a,b-MeATP from rat urinary bladder P2X receptor measured aft... 27876250
Unchecked IC50 = 2.1 nM 8.68 Binding affinity to P2X receptor (unknown origin) by radioligand displacement as... 23466604
Unchecked IC50 = 3.5 nM 8.46 Binding affinity to P2X receptor (unknown origin) by radioligand displacement as... 23582449
Unchecked Ki = 4.8 nM 8.32 Displacement of radiolabeled alpha, beta -MeATP from P2X receptor 18983139
Unchecked IC50 = 10.0 nM 8.0 Displacement of radiolabeled alpha, beta -MeATP from P2X receptor 18983139
Unchecked IC50 = 14.0 nM 7.85 Percent inhibition against P2Y Purinoceptor at 1 uM 16250647
Unchecked Ki = 18.0 nM 7.75 Displacement of [3H]alpha, beta-methylene-ATP from purinergic P2X receptor in Ne... 23403082
Unchecked IC50 = 82.0 nM 7.09 Displacement of [3H]alpha, beta-methylene-ATP from purinergic P2X receptor in Ne... 23403082
P2X purinoceptor 1 EC50 = 200.0 nM 6.7 Antagonist activity against recombinant human P2X purinoceptor 1 (P2X1 ) 12213051
P2X purinoceptor 3 EC50 = 740.0 nM 6.13 Antagonist activity against recombinant human P2X purinoceptor 3 (P2X3 ) 12213051
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 2200.0 nM 5.66 Competitive-inhibition of Wistar rat NPP1 using p-Nph-5'-TMP as substrate measur... 30108800
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 3320.0 nM 5.48 Competitive-inhibition of recombinant human N-terminal His-tagged soluble NPP1 (... 30108800
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 5000.0 nM 5.3 Inhibition of recombinant human ENPP1 using ATP as substrate assessed as inhibit... 38359537
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 8190.0 nM 5.09 Competitive-inhibition of recombinant human N-terminal His-tagged soluble NPP1 (... 30108800
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 13000.0 nM 4.89 Competitive-inhibition of recombinant human N-terminal His-tagged soluble NPP1 (... 30108800
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 Ki = 26900.0 nM 4.57 Competitive-inhibition of recombinant human N-terminal His-tagged soluble NPP1 (... 30108800
P2X purinoceptor 4 EC50 = 33000.0 nM 4.48 Antagonist activity against recombinant rat P2X purinoceptor 4 (P2X4) at 30 uM, ... 12213051
P2X purinoceptor 2 EC50 = 100000.0 nM 4.0 Antagonist activity against recombinant rat receptor P2X purinoceptor 2 (P2X2) a... 12213051

Literature References

PubMed DOI Target Context # Activities
30108800 10.1039/C7MD00015D Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 5
3950912 10.1021/jm00153a003 S-adenosylmethionine synthetase (MAT 1 and MAT 2) 3
23403082 10.1016/j.bmcl.2013.01.025 Unchecked 3
23466604 10.1016/j.ejmech.2013.01.044 Unchecked 2
3950912 10.1021/jm00153a003 S-adenosylmethionine synthase isoform type-2 2
21641210 10.1016/j.bmcl.2011.05.021 Pantothenate synthetase 2
18983139 10.1021/jm8007618 Unchecked 2
12213051 10.1021/jm020046y P2Y purinoceptor 12 1
12213051 10.1021/jm020046y P2X purinoceptor 2 1
38359537 10.1016/j.ejmech.2024.116211 Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 1
26988801 10.1016/j.bmc.2016.03.006 Unchecked 1
12213051 10.1021/jm020046y P2X purinoceptor 1 1
23582449 10.1016/j.bmc.2013.03.016 Unchecked 1
19606867 10.1021/jm900131v P2X purinoceptor 3 1
16250647 10.1021/jm058018d Unchecked 1
12213051 10.1021/jm020046y P2Y purinoceptor 1 1
12213051 10.1021/jm020046y P2X purinoceptor 7 1
12213051 10.1021/jm020046y P2X purinoceptor 6 1
12213051 10.1021/jm020046y P2X purinoceptor 5 1
12213051 10.1021/jm020046y P2X purinoceptor 4 1

Data from ChEMBL 36 via Core Engine