Structure

InChI Key VCMJCVGFSROFHV-WZGZYPNHSA-N
Smiles CC(C)OC(=O)OCOP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)OCOC(=O)OC(C)C.O=C(O)/C=C/C(=O)O
InChI
InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H34N5O14P
Molecular Weight 635.52
AlogP 3.04
Hydrogen Bond Acceptor 15.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 13.0
Polar Surface Area 185.44
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 35.0

Pharmacology

Mechanism of Action Action Reference
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR DailyMed
Assay Description Organism Bioactivity Reference
Inhibition of virus-induced cytopathic effect in wild type HIV 3a infected MT2 cells after 5 days Human immunodeficiency virus 1 15.0 nM
Antiviral activity against HIV1 3B infected in human MT-2 cells by two fold dilution method in presence of 10% FBS Human immunodeficiency virus 1 6.8 nM
Antiviral activity against HIV1 infected in human MT2 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 540.0 nM
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication Human immunodeficiency virus 1 14.0 nM
Antiviral activity against HIV1 NL4-3.Luc assessed as infectivity using human MDM pretreated for 24 hrs followed by exposed to virus after compound washout measured after 2 to 3 days by luciferase assay Human immunodeficiency virus 1 34.0 nM
Antiviral activity against HIV1 NL4-3.Luc assessed as infectivity using human PBMC pretreated for 24 hrs followed by exposed to virus after compound washout measured after 2 to 3 days by luciferase assay Human immunodeficiency virus 1 55.0 nM
Antiviral activity against single-round HIV1 NLX.Lux-R harboring inactivating mutations in env, vpr and carries firefly luciferase gene in place of nef infected in human HeLa-T4 cells assessed as luciferase activity after 48 hrs by exogenous RT assay Human immunodeficiency virus 1 2.9 nM
Antiviral activity against single-round HIV1 NLX.Lux-R harboring inactivating mutations in env, vpr and carries firefly luciferase gene in place of nef assessed as level of infection using human HeLaT4 cells pretreated for 24 hrs followed by exposed to virus immediately after 3 times compound washout Human immunodeficiency virus 1 120.0 nM
Antiviral activity against HIV1 NL4-3.Luc in human PBMC assessed as infectivity treated for 24 hrs by luciferase assay Human immunodeficiency virus 1 46.0 nM
Antiviral activity against HIV1 NL4-3.Luc in human MDM assessed as infectivity treated for 24 hrs by luciferase assay Human immunodeficiency virus 1 28.0 nM
Antiviral activity against CXCR4-tropic HIV-1 NL4-3 infected in human PHA-stimulated PBMC assessed as inhibition of viral replication by measuring reduction in p24 antigen production preincubated with cells for 30 mins followed by viral infection measured on day 10 post infection in presence of IL-2 by ELISA Human immunodeficiency virus 1 80.0 nM
Antiviral activity against CCR5 tropic HIV1 BaL infected in human PHA-stimulated PBMC assessed as inhibition of viral replication by measuring reduction in p24 antigen production preincubated with cells for 30 mins followed by viral infection measured on day 10 post infection in presence of IL-2 by ELISA Human immunodeficiency virus 1 220.0 nM
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as reduction in cytoplasmic DNA synthesis by reed and munch method Hepatitis B virus 850.0 nM
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication by measuring reverse transcriptase activity in cell supernatant preincubated with cells followed by viral infection measured after 7 days by radioactive incorporation polymerization assay Human immunodeficiency virus 1 4.6 nM
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as inhibition of viral DNA in cell supernatant incubated for 3 days in presence of 10% FBS followed by compound treatment in absence of 10% FBS for 3 days by qRT-PCR method Hepatitis B virus 340.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2.2.15 cells assessed as reduction in HBV DNA level in cell supernatants incubated for 5 days by real time PCR analysis Hepatitis B virus 13.79 nM
Antiviral activity against HIV1 infected in human PBMC assessed as reduction in viral replication incubated for 7 days by radioactive incorporation polymerization assay based reverse transcriptase activity detection method Human immunodeficiency virus 1 4.5 nM
Antiviral activity against HBV infected in human HepG2 assessed as reduction in viral replication incubated for 6 days by real time Q-PCR analysis Hepatitis B virus 340.0 nM
Antiviral activity against HIV-1 Human immunodeficiency virus 1 50.0 nM

Cross References

Resources Reference
ChEBI 63718
ChEMBL CHEMBL1486
FDA SRS OTT9J7900I
PubChem 6398764
SureChEMBL SCHEMBL40021