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Compound Detail

CHEMBL1230

LAMIVUDINE TRIPHOSPHATE
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Nc1ccn([C@@H]2CS[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1230
Name LAMIVUDINE TRIPHOSPHATE
Phase Preclinical
Structure Type MOL
InChI Key YLEQMGZZMCJKCN-NKWVEPMBSA-N

Known Names

3tc triphosphate 3tc-tp Lamivudine 5'-triphosphate Lamivudine triphosphate
4
Targets
16
Activities
3
Assay Types
1
PK Parameters
16
Publications
4
Known Names

Molecular Properties

469.2
MW (Da)
-0.24
ALogP
12
HBA
5
HBD
230.0
PSA (Ų)
0.31
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Single Enantiomer
USAN Stem -vudine

Extended Properties

Molecular Formula C8H14N3O12P3S
MW 469.20
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness 1.30

Activity Summary

Kd 10 meas. best 6.89
IC50 5 meas. best 8.12
Ki 1 meas. best 6.73

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis B virus
CHEMBL613497
 IC50 8.12 8.12 7.5 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 7.82 7.82 15.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Kd 6.89 5.7238 130.0 8
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Ki 6.73 6.73 188.0 1
Unchecked
CHEMBL612545
 IC50 6.52 5.7433 300.0 3
DNA polymerase subunit gamma-1
CHEMBL2732
 Kd 4.89 4.89 13000.0 1
Unchecked
CHEMBL612545
 Kd 4.75 4.75 17800.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 3.0 hr Bos taurus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis B virus IC50 = 7.5 nM 8.12 Antiviral activity against Hepatitis B virus 19112024
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 15.0 nM 7.82 Inhibition of full-length wild-type HIV1 reverse transcriptase expressed in Esch... 30265808
Human immunodeficiency virus type 1 reverse transcriptase Kd = 130.0 nM 6.89 Binding affinity to HIV1 reverse transcriptase assessed as L-3'-azido-NTP incorp... 21700368
Human immunodeficiency virus type 1 reverse transcriptase Ki = 188.0 nM 6.73 Inhibitory constant against HIV-1 reverse transcriptase 15801860
Unchecked IC50 = 300.0 nM 6.52 Inhibition of HBV DNA polymerase 17404006
Human immunodeficiency virus type 1 reverse transcriptase Kd = 370.0 nM 6.43 Binding affinity to wild type HIV1 LAI reverse transcriptase 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 370.0 nM 6.43 Binding affinity to HIV1 reverse transcriptase 19596885
Human immunodeficiency virus type 1 reverse transcriptase Kd = 430.0 nM 6.37 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant 17967907
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of recombinant wild type HIV reverse transcriptase 17434736
Unchecked IC50 = 6500.0 nM 5.19 Inhibition of wild type HIV reverse transcriptase in PBM cells 17434736
Human immunodeficiency virus type 1 reverse transcriptase Kd = 8200.0 nM 5.09 Binding affinity to HIV1 LAI reverse transcriptase M184V mutant 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 9800.0 nM 5.01 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant 17967907
DNA polymerase subunit gamma-1 Kd = 13000.0 nM 4.89 Binding affinity to human DNA polymerase gamma assessed as dissociation constant 37393791
Human immunodeficiency virus type 1 reverse transcriptase Kd = 15000.0 nM 4.82 Equilibrium binding constant at the active site of HIV-1 reverse transcriptase 14698176
Unchecked Kd = 17800.0 nM 4.75 Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D ... 17967907
Human immunodeficiency virus type 1 reverse transcriptase Kd = 18000.0 nM 4.75 Binding affinity to HIV1 reverse transcriptase M184V mutant assessed as L-3'-azi... 21700368

Literature References

PubMed DOI Target Context # Activities
17967907 10.1128/aac.00904-07 Human immunodeficiency virus type 1 reverse transcriptase 11
21700368 10.1016/j.ejmech.2011.05.051 Human immunodeficiency virus type 1 reverse transcriptase 6
19596885 10.1128/aac.00392-09 Human immunodeficiency virus type 1 reverse transcriptase 4
14698176 10.1016/j.bmcl.2003.10.042 Human immunodeficiency virus type 1 reverse transcriptase 3
17434736 10.1016/j.bmcl.2007.03.094 Unchecked 3
17967907 10.1128/aac.00904-07 Unchecked 3
37393791 10.1016/j.ejmech.2023.115586 DNA polymerase subunit gamma-1 3
15801860 10.1021/jm040101y Human immunodeficiency virus type 1 reverse transcriptase 1
15801860 10.1021/jm040101y ADMET 1
17434736 10.1016/j.bmcl.2007.03.094 Human immunodeficiency virus type 1 reverse transcriptase 1
17403996 10.1128/aac.01543-06 CCRF-CEM 1
17403996 10.1128/aac.01543-06 PBMC 1
17404006 10.1128/aac.00001-07 Unchecked 1
19112024 10.1016/j.bmc.2008.11.075 Hepatitis B virus 1
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 1
30265808 10.1021/acs.jmedchem.8b00141 Human immunodeficiency virus type 1 reverse transcriptase 1

Data from ChEMBL 36 via Core Engine