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Compound Detail

CHEMBL404519

BEVIRIMAT
🧪 Phase II
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🧪 Phase II
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)CC(C)(C)C(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Basic Information

ChEMBL ID CHEMBL404519
Name BEVIRIMAT
Phase Phase II
Structure Type MOL
InChI Key YJEJKUQEXFSVCJ-WRFMNRASSA-N

Known Names

Bevirimat MPC-4326 PA-103001 Yk-fh312
11
Targets
88
Activities
3
Assay Types
30
PK Parameters
20
Publications
4
Known Names
2
Indications

Molecular Properties

584.8
MW (Da)
8.14
ALogP
4
HBA
2
HBD
100.9
PSA (Ų)
0.24
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir-
USAN Year 2006

Extended Properties

Molecular Formula C36H56O6
MW 584.84
Aromatic Rings 0
Heavy Atoms 42
NP-Likeness 2.69

Indications

HIV Infections HIV Infections

Activity Summary

EC50 59 meas. best 10.3
IC50 27 meas. best 8.0
Ki 2 meas. best 5.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 10.3 7.5697 0.1 30
H9
CHEMBL614806
EC50 9.46 8.805 0.3 2
Unchecked
CHEMBL612545
EC50 8.15 7.0147 7.0 17
Gag-Pol polyprotein
CHEMBL3638360
EC50 8.0 7.014 10.0 5
Human immunodeficiency virus 1
CHEMBL378
IC50 8.0 6.9418 10.0 11
Human immunodeficiency virus
CHEMBL613758
EC50 7.99 7.99 10.3 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 7.19 6.15 65.0 2
MT4
CHEMBL388
EC50 7.02 6.8033 96.0 3
Unchecked
CHEMBL612545
IC50 6.6 5.7314 252.0 7
Gag-Pol polyprotein
CHEMBL3638360
IC50 6.26 6.26 552.0 1
Unchecked
CHEMBL612545
Ki 5.36 5.36 4400.0 1
H9
CHEMBL614806
IC50 5.16 5.16 7000.0 2
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
Ki 5.16 5.16 7000.0 1
Leishmania donovani
CHEMBL367
IC50 5.14 5.14 7200.0 1
MT4
CHEMBL388
IC50 4.82 4.82 15200.0 1
MT2
CHEMBL614184
IC50 4.37 4.37 42780.0 1
THP-1
CHEMBL614245
IC50 4.27 4.27 54000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 151200.0 ng.hr.mL-1 Homo sapiens
AUC 312100.0 ng.hr.mL-1 Homo sapiens
AUC 982800.0 ng.hr.mL-1 Homo sapiens
AUC 1795700.0 ng.hr.mL-1 Homo sapiens
AUC 170200.0 ng.hr.mL-1 Homo sapiens
AUC 362100.0 ng.hr.mL-1 Homo sapiens
AUC 1014000.0 ng.hr.mL-1 Homo sapiens
AUC 2221800.0 ng.hr.mL-1 Homo sapiens
AUC 3737.13 ng.hr.mL-1 Rattus norvegicus
AUC 3737.13 ng.hr.mL-1 Rattus norvegicus
AUC 8047.4 ng.hr.mL-1 Rattus norvegicus
AUC 3737.13 ng.hr.mL-1 Rattus norvegicus
AUC 3737127.6 ng.hr.mL-1 Rattus norvegicus
AUC 8049152.92 ng.hr.mL-1 Rattus norvegicus
AUC 3737.13 ng.hr.mL-1 Rattus norvegicus
AUC 3742.98 ng.hr.mL-1 Rattus norvegicus
AUC 0.008071 ng.hr.mL-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.7 mL.min-1.kg-1 Rattus norvegicus
Cmax 3830.11 nM Homo sapiens
Cmax 10361.81 nM Homo sapiens
Cmax 23339.72 nM Homo sapiens
Cmax 51381.57 nM Homo sapiens
Cmax 4787.63 nM Homo sapiens
Cmax 12482.05 nM Homo sapiens
Cmax 25477.05 nM Homo sapiens
Cmax 53176.94 nM Homo sapiens
Cmax 2587.0 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.05 nM 10.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 0.2999 nM 9.52 Antiviral activity against Human immunodeficiency virus 1 infected human H9 cell... -
H9 EC50 = 0.35 nM 9.46 Cytotoxicity against human H9 cells after 4 days by coulter counter 20187635
Human immunodeficiency virus 1 EC50 = 0.35 nM 9.46 Antiviral activity against Human immunodeficiency virus 1 infected human H9 cell... -
Human immunodeficiency virus 1 EC50 = 0.35 nM 9.46 Antiviral activity against HIV1 infected in human H9 cells 26968652
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 1.3 nM 8.89 Antiviral activity against HIV1 17935987
Human immunodeficiency virus 1 EC50 = 1.3 nM 8.89 Antiviral activity against HIV1 3B infected in human MT2 cells assessed as inhib... 20329730
H9 EC50 = 7.0 nM 8.15 Antiviral activity against HIV1 3B in H9 lymphocytes 16942019
Unchecked EC50 = 7.0 nM 8.15 Binding affinity to gag polyprotein Q369H mutant in HIV1 NLRepRlucP373S infected... 27326328
Unchecked EC50 = 8.0 nM 8.1 Binding affinity to HIV-1 CA-SP1 cleavage site of Gag-Pol protein harboring G369... 30891128
Human immunodeficiency virus 1 EC50 = 9.0 nM 8.05 Antiviral activity against wild type HIV1 infected in human HeLa cells assessed ... 19805571
Unchecked EC50 = 9.0 nM 8.05 Binding affinity to wild type HIV-1 NL4-3 CA-SP1 cleavage site of Gag-Pol protei... 30891128
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against HIV1 NL4.3-Ren infected in human MT2 cells assessed a... 25927586
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against HIV1 clinical isolates 19223634
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against wild type HIV-1 NLRepRlucP373S infected in human MT2 ... 36441509
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against wild type HIV-1 NL4-3 infected in MT-2 cells assessed... 33508465
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against wild type HIV1 NLRepRlucP373S infected in human MT2 c... 26968652
Unchecked EC50 = 10.0 nM 8.0 Binding affinity to HIV-1 CA-SP1 cleavage site of Gag-Pol protein harboring Thr3... 30891128
Gag-Pol polyprotein EC50 = 10.0 nM 8.0 Binding affinity to CA-SP1 P373S mutant in HIV-1 subtype B NL4-3 infected in hum... 29631960

Literature References

PubMed DOI Target Context # Activities
20308382 10.1128/aac.01784-09 Human immunodeficiency virus 1 46
19223634 10.1128/aac.01650-08 Human immunodeficiency virus 1 44
17576843 10.1128/aac.01391-06 Homo sapiens 32
17638699 10.1128/aac.00152-07 Human immunodeficiency virus 1 28
17638699 10.1128/aac.00152-07 Homo sapiens 24
30891128 10.1021/acsmedchemlett.8b00656 Unchecked 11
27326328 10.1021/acsmedchemlett.6b00010 Unchecked 10
33508465 10.1016/j.bmcl.2021.127823 ADMET 9
29631960 10.1016/j.bmcl.2018.03.067 Gag-Pol polyprotein 8
28454672 10.1016/j.bmcl.2017.04.042 Unchecked 8
23379607 10.1021/jm3016969 Human immunodeficiency virus 1 7
26988305 10.1016/j.bmcl.2016.03.019 Human immunodeficiency virus 1 7
26988305 10.1016/j.bmcl.2016.03.019 Rattus norvegicus 6
26968652 10.1016/j.bmc.2016.03.001 Rattus norvegicus 6
19805571 10.1128/aac.00759-09 Human immunodeficiency virus 1 5
16942019 10.1021/jm0601912 MT4 5
26968652 10.1016/j.bmc.2016.03.001 Human immunodeficiency virus 1 5
19481937 10.1016/j.bmcl.2009.05.050 Unchecked 5
24411124 10.1016/j.bmcl.2013.12.041 Unchecked 5
30891128 10.1021/acsmedchemlett.8b00656 ADMET 5

Data from ChEMBL 36 via Core Engine