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Compound Detail

CHEMBL286534

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Nc1ncnc2c1ncn2C[C@@H](CO)OCP(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL286534
Phase Preclinical
Structure Type MOL
InChI Key FRPXSOOHWNMLPH-LURJTMIESA-N
13
Targets
37
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

303.2
MW (Da)
-1.08
ALogP
8
HBA
4
HBD
156.6
PSA (Ų)
0.49
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H14N5O5P
MW 303.21
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.09

Activity Summary

EC50 28 meas. best 7.44
IC50 9 meas. best 6.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human betaherpesvirus 5
CHEMBL371
 EC50 7.44 6.4556 36.0 9
Murid betaherpesvirus 1
CHEMBL613495
 EC50 6.8 6.8 160.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.75 6.75 180.0 1
Human betaherpesvirus 5
CHEMBL371
 IC50 6.39 6.39 410.0 1
Camelpox virus
CHEMBL613332
 EC50 6.3 6.1125 500.0 4
Human adenovirus 2
CHEMBL613715
 IC50 6.2 6.2 630.0 1
Unchecked
CHEMBL612545
 EC50 6.0 6.0 1000.0 1
Hepatitis B virus
CHEMBL613497
 EC50 5.92 5.92 1200.0 1
Vaccinia virus
CHEMBL613493
 IC50 5.7 5.58 2000.0 2
Vaccinia virus
CHEMBL613493
 EC50 5.57 5.4433 2700.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.4 5.4 4000.0 1
Cowpox virus
CHEMBL612672
 EC50 5.4 5.4 4000.0 2
Cowpox virus
CHEMBL612672
 IC50 5.3 5.3 5000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.02 4.94 9500.0 4
Simian virus 40
CHEMBL613051
 EC50 4.99 4.9033 10200.0 3
Human alphaherpesvirus 1
CHEMBL377
 IC50 4.46 4.46 35000.0 1
HFF
CHEMBL614071
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 24.0 % Mus musculus
F 39.0 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human betaherpesvirus 5 EC50 = 36.0 nM 7.44 Antiviral activity against foscarnet-resistant HCMV AD169 clone C infected in HE... 19226140
Human betaherpesvirus 5 EC50 = 80.0 nM 7.1 Antiviral activity against acyclovir-resistant HCMV AD169 clone 1 infected in HE... 19226140
Human betaherpesvirus 5 EC50 = 120.0 nM 6.92 Antiviral activity against PMEDAP-resistant HCMV AD169 clone 4 infected in HEL c... 19226140
Murid betaherpesvirus 1 EC50 = 160.0 nM 6.8 Antiviral activity against MCMV Smith replication 16539388
Human betaherpesvirus 5 EC50 = 170.0 nM 6.77 Antiviral activity against wild type HCMV AD169 infected in HEL cells assessed a... 19226140
Plasmodium falciparum IC50 = 180.0 nM 6.75 Antimalarial activity against synchronized Plasmodium falciparum K1 ring form in... 30964283
Human betaherpesvirus 5 EC50 = 200.0 nM 6.7 Antiviral activity against wild type HCMV Davis infected in HEL cells assessed a... 19226140
Human betaherpesvirus 5 IC50 = 410.0 nM 6.39 Antiviral activity against HCMV Towne infected in HFF cells incubated for 10 day... 21812420
Camelpox virus EC50 = 500.0 nM 6.3 Antiviral activity against Camelpox virus CML14 infected in HEL299 cells assesse... 17893157
Camelpox virus EC50 = 500.0 nM 6.3 Antiviral activity against Camelpox virus CML1 infected in HEL299 cells assessed... 17893157
Human adenovirus 2 IC50 = 630.0 nM 6.2 Antiviral activity against Human adenovirus 2 19112024
Human betaherpesvirus 5 EC50 = 820.0 nM 6.09 Antiviral activity against HCMV AD-169 replication 16539388
Camelpox virus EC50 = 1000.0 nM 6.0 Antiviral activity against Camelpox virus CML1 infected in human PHK assessed as... 17893157
Unchecked EC50 = 1000.0 nM 6.0 Antiviral activity against HCMV AD169 infected in human embryonic lung cells 34124679
Hepatitis B virus EC50 = 1200.0 nM 5.92 Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as... 19398648
Camelpox virus EC50 = 1400.0 nM 5.85 Antiviral activity against Camelpox virus CML14 infected in human PHK assessed a... 17893157
Human betaherpesvirus 5 EC50 = 1900.0 nM 5.72 Antiviral activity against HPMPA-resistant HCMV AD169 clone 2 mutant infected in... 19226140
Vaccinia virus IC50 = 2000.0 nM 5.7 Antiviral activity against Vaccinia virus Copenhagen infected in HFF cells incub... 21812420
Human betaherpesvirus 5 EC50 = 2100.0 nM 5.68 Antiviral activity against cidofovir HCMV AD169 clone 5 infected in human HEL ce... 19226140
Human betaherpesvirus 5 EC50 = 2100.0 nM 5.68 Antiviral activity against ganciclovir-resistant HCMV AD169 clone 4 infected in ... 19226140

Literature References

PubMed DOI Target Context # Activities
8765509 10.1021/jm9601314 MT4 13
7877148 10.1021/jm00005a010 E6SM 11
17893157 10.1128/aac.00838-07 Camelpox virus 10
18707089 10.1021/jm800050t Human betaherpesvirus 5 8
19226140 10.1021/jm8014662 Human betaherpesvirus 5 8
19398648 10.1128/aac.00114-09 HepG2 8
17420214 10.1128/aac.01422-06 Unchecked 7
19704122 10.1128/aac.00840-09 Schistosoma mansoni 7
16539388 10.1021/jm050473m HFF 5
17893157 10.1128/aac.00838-07 ADMET 4
17420214 10.1128/aac.01422-06 NON-PROTEIN TARGET 4
17893157 10.1128/aac.00838-07 Unchecked 4
17420214 10.1128/aac.01422-06 Simian virus 40 3
17846137 10.1128/aac.00184-07 Unchecked 3
19398648 10.1128/aac.00114-09 Hepatitis B virus 2
17420214 10.1128/aac.01422-06 ADMET 2
19289518 10.1128/aac.01546-08 Hepatitis C virus 2
2544723 10.1021/jm00127a010 Human alphaherpesvirus 1 2
17846137 10.1128/aac.00184-07 Vaccinia virus 2
2391689 10.1021/jm00171a022 Human immunodeficiency virus 1 1

Data from ChEMBL 36 via Core Engine