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Compound Detail

CHEMBL257695

AZIDOTHYMIDINE MONOPHOSPHATE
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Cc1cn([C@H]2C[C@H](N=[N+]=[N-])[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL257695
Name AZIDOTHYMIDINE MONOPHOSPHATE
Phase Preclinical
Structure Type MOL
InChI Key OIFWQOKDSPDILA-XLPZGREQSA-N
5
Targets
17
Activities
4
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

347.2
MW (Da)
-0.08
ALogP
7
HBA
3
HBD
179.6
PSA (Ų)
0.29
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H14N5O7P
MW 347.22
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 0.96

Activity Summary

Kd 8 meas. best 7.73
IC50 4 meas. best 5.3
Ki 4 meas. best 5.0
EC50 1 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.0 8.0 10.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Kd 7.73 6.9733 18.8 6
Unchecked
CHEMBL612545
 Kd 7.65 7.49 22.3 2
Unchecked
CHEMBL612545
 IC50 5.3 5.3 5000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.16 4.615 7000.0 2
Thymidylate kinase
CHEMBL2361
 Ki 5.0 5.0 10000.0 4

Pharmacokinetic Data

Parameter Value Units Species
T1/2 50.0 hr -
T1/2 4.0 hr -
T1/2 72.0 hr -
T1/2 4.0 hr -
T1/2 67.0 hr -
T1/2 4.0 hr -
T1/2 3.6 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HIV1 infected in human CEM-T4 cells assessed as reduc... 21834513
Human immunodeficiency virus type 1 reverse transcriptase Kd = 18.8 nM 7.73 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant asses... 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 19.8 nM 7.7 Binding affinity to wild type HIV1 LAI reverse transcriptase assessed as ATP-med... 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 20.5 nM 7.69 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R mutant ... 17967907
Unchecked Kd = 22.3 nM 7.65 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R/G333D m... 17967907
Unchecked Kd = 46.2 nM 7.33 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D ... 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 76.9 nM 7.11 Binding affinity to HIV1 LAI reverse transcriptase M184V mutant assessed as ATP-... 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 98.4 nM 7.01 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant... 17967907
Unchecked IC50 = 5000.0 nM 5.3 The compound was tested for extent of UDP-[3H]-GlcNAc accumulation into the lume... 8709123
Unchecked IC50 = 5000.0 nM 5.3 Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in th... 8709123
NON-PROTEIN TARGET IC50 = 7000.0 nM 5.16 In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membra... 8709123
Thymidylate kinase Ki = 10000.0 nM 5.0 Inhibitory activity against thymidine monophosphate kinase (TMPK) in Mycobacteri... 12941330
Thymidylate kinase Ki = 10000.0 nM 5.0 In Vitro inhibition of Thymidine Monophosphatase Kinase of Mycobacterium tubercu... 12930144
Thymidylate kinase Ki = 10000.0 nM 5.0 Compound was tested for binding affinity against Mycobacterium tuberculosis thym... 12217356
Thymidylate kinase Ki = 10000.0 nM 5.0 Competitive inhibition of Mycobacterium tuberculosis TMPK expressed in Escherich... 22061826
Human immunodeficiency virus type 1 reverse transcriptase Kd = 24900.0 nM 4.6 Binding affinity to ternary complex of HIV1 reverse transcriptase with primer/te... 17517852
NON-PROTEIN TARGET IC50 = 85000.0 nM 4.07 In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membra... 8709123

Literature References

PubMed DOI Target Context # Activities
17517852 10.1128/aac.00314-07 Human immunodeficiency virus type 1 reverse transcriptase 19
17967907 10.1128/aac.00904-07 Human immunodeficiency virus type 1 reverse transcriptase 13
17967907 10.1128/aac.00904-07 Unchecked 12
7562927 10.1021/jm00020a007 ADMET 6
8709123 10.1021/jm960175c Unchecked 4
1501232 10.1021/jm00094a018 Mus musculus 3
17353236 10.1128/aac.01432-06 Thymidylate kinase 3
8709123 10.1021/jm960175c NON-PROTEIN TARGET 2
10698446 10.1016/s0960-894x(99)00677-0 Human immunodeficiency virus type 1 integrase 2
17517852 10.1128/aac.00314-07 Unchecked 2
10470083 10.1038/12487 ATP-binding cassette sub-family C member 4 1
12941330 10.1016/s0960-894x(03)00643-7 Thymidylate kinase 1
21834513 10.1021/jm2001103 ADMET 1
21834513 10.1021/jm2001103 No relevant target 1
21128666 10.1021/jm1011462 Thymidylate kinase 1
- 10.1016/S0960-894X(01)80437-6 Human immunodeficiency virus type 1 reverse transcriptase 1
- 10.1016/S0960-894X(01)80437-6 Avian myeloblastosis virus 1
12217356 10.1016/s0960-894x(02)00551-6 Thymidylate kinase 1
12930144 10.1021/jm021108n Unchecked 1
12930144 10.1021/jm021108n Thymidine kinase, cytosolic 1

Data from ChEMBL 36 via Core Engine