Peramivir

AlkaPlorer ID: AK096781

Synonym: None

IUPAC Name: (1S,2S,3S,4R)-3-[(1S)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid

Structure

SMILES: CCC(CC)[C@H](N=C(C)O)[C@@H]1[C@H](O)[C@@H](C(=O)O)C[C@H]1NC(=N)N

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InChI: InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12-,13+/m0/s1

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InChIKey: XRQDFNLINLXZLB-CKIKVBCHSA-N

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Reference

PubChem CID: 154234

CAS: 229614-55-5

NPASS: NPC487423

Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 328.41300000000007

TPSA: 152.02000000000004

MolLogP: 0.7008700000000014

Number of H-Donors: 6

Number of H-Acceptors: 4

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Canis lupus familiaris MDCK CC50 100000.0 nM 10.1016/j.ejmech.2017.12.072
Canis lupus familiaris MDCK CC50 100000.0 nM 10.1016/j.ejmech.2021.113929
Canis lupus familiaris MDCK CC50 100000.0 nM 10.1021/acs.jmedchem.6b00029
Canis lupus familiaris MDCK CC50 200000.0 nM 10.1016/j.ejmech.2020.112048
Canis lupus familiaris MDCK CC50 373000.0 nM 10.1016/j.bmcl.2017.11.003
Clostridium perfringens Sialidase IC50 39600.0 nM 10.1016/j.bmcl.2017.11.003
Homo sapiens Histone deacetylase 6 Inhibition -29.82 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -2.34 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens Activity 1.0 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity 2.0 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity 3.0 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity 6.1 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity 14.1 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity 15.2 % 10.1128/aac.00474-10
Homo sapiens Homo sapiens Activity nan None 10.1128/aac.00474-10
Homo sapiens Homo sapiens Cmax 30449.74 nM 10.1128/aac.00334-09
Homo sapiens Plasma Cp 5.01 ng/ml 10.1128/aac.00474-10
Homo sapiens Plasma Cp 10.7 ng/ml 10.1128/aac.00474-10
Homo sapiens Plasma Cp 14.8 ng/ml 10.1128/aac.00474-10
Homo sapiens Plasma Cp 32.8 ng/ml 10.1128/aac.00474-10
Homo sapiens Plasma Cp 18100.0 ng/ml 10.1128/aac.00474-10
Homo sapiens Plasma Cp 36300.0 ng/ml 10.1128/aac.00474-10
Homo sapiens Sialidase 1 IC50 500000.0 nM 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 1 IC50 500000.0 nM 10.1021/acs.jmedchem.1c01612
Homo sapiens Sialidase 1 Ki nan None 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 2 IC50 70000.0 nM 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 2 Ki 56000.0 nM 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 2 Ki 330000.0 nM 10.1021/jm100078r
Homo sapiens Sialidase 3 IC50 500000.0 nM 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 3 IC50 500000.0 nM 10.1021/acs.jmedchem.1c01612
Homo sapiens Sialidase 3 Ki nan None 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 4 IC50 500000.0 nM 10.1016/j.bmc.2018.05.035
Homo sapiens Sialidase 4 IC50 500000.0 nM 10.1021/acs.jmedchem.1c01612
Homo sapiens Sialidase 4 Ki nan None 10.1016/j.bmc.2018.05.035
Influenza A virus Influenza A virus Activity nan None 10.1021/acs.jmedchem.1c01531
Influenza A virus Influenza A virus Activity nan None 10.1128/aac.01681-09
Influenza A virus Influenza A virus EC50 1.5 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Influenza A virus EC50 6.68 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Influenza A virus EC50 643.0 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Influenza A virus EC50 5260.0 nM 10.1016/j.ejmech.2020.112048
Influenza A virus Influenza A virus EC50 5260.0 nM 10.1016/j.ejmech.2021.113929
Influenza A virus Influenza A virus FC 1.5 None 10.1128/aac.01681-09
Influenza A virus Influenza A virus FC 5.0 None 10.1128/aac.01681-09
Influenza A virus Influenza A virus IC50 0.08 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.11 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.12 nM 10.1016/j.bmcl.2011.09.076
Influenza A virus Influenza A virus IC50 0.12 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.14 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.18 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.19 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.2 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 0.2 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.28 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 0.3 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 0.32 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.41 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.43 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 0.49 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.5 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 0.51 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 0.55 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.7 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.75 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 0.86 nM 10.1016/j.bmcl.2011.09.076
Influenza A virus Influenza A virus IC50 0.9 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 1.0 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 1.47 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 1.72 nM 10.1128/aac.00474-10
Influenza A virus Influenza A virus IC50 3.0 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 3.51 nM 10.1128/aac.00474-10
Influenza A virus Influenza A virus IC50 9.24 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 9.43 nM 10.1128/aac.00474-10
Influenza A virus Influenza A virus IC50 11.79 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 12.5 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 13.06 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 13.75 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 14.96 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 27.0 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 33.56 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 43.6 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 82.8 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 83.4 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 84.8 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 95.5 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 97.56 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 105.02 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 121.76 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 128.15 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 142.4 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 149.59 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 150.24 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 161.79 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 162.58 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 194.96 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 197.1 nM 10.1128/aac.00581-10
Influenza A virus Influenza A virus IC50 200.0 nM 10.1016/j.bmc.2008.11.075
Influenza A virus Influenza A virus IC50 213.0 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 214.07 nM 10.1128/aac.01608-09
Influenza A virus Influenza A virus IC50 562.1 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 891.4 nM 10.1128/aac.00334-09
Influenza A virus Influenza A virus IC50 1720.0 nM 10.1016/j.bmcl.2017.11.003
Influenza A virus Influenza A virus IC50 nan None 10.1128/aac.01608-09
Influenza A virus Influenza A virus Ratio IC50 1.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 1.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 4.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 12.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 66.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 84.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 89.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 93.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 108.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 111.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 125.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 136.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 140.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 164.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 173.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 330.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 332.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 347.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 398.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 400.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 488.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 533.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 609.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 641.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 751.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 831.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 893.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 1095.0 None 10.1128/aac.00581-10
Influenza A virus Influenza A virus Ratio IC50 2106.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Ratio IC50 3340.0 None 10.1128/aac.00334-09
Influenza A virus Influenza A virus Survival 50.0 % 10.1128/aac.01681-09
Influenza A virus Influenza A virus Survival 100.0 % 10.1128/aac.01681-09
Influenza A virus Influenza A virus TIME 50.5 hr 10.1128/aac.00474-10
Influenza A virus Influenza A virus TIME 52.5 hr 10.1128/aac.00474-10
Influenza A virus Influenza A virus TIME 62.6 hr 10.1128/aac.00474-10
Influenza A virus Influenza A virus TIME 76.1 hr 10.1128/aac.00474-10
Influenza A virus Neuraminidase IC50 0.07 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 0.1 nM 10.1039/C4MD00168K
Influenza A virus Neuraminidase IC50 0.3 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 0.3 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 0.7 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 0.8 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 3.3 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 3.6 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 3.6 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 18.4 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 23.1 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 92.5 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 146.0 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 146.0 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 225.0 nM 10.1021/acs.jmedchem.6b00029
Influenza A virus Neuraminidase IC50 451.0 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus Neuraminidase IC50 10000.0 nM 10.1016/j.ejmech.2007.04.011
Influenza A virus Neuraminidase Inhibition nan % 10.1016/j.bmcl.2011.09.076
Influenza A virus (A/Memphis/1/1971(H3N2)) Neuraminidase IC50 2.0 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Neuraminidase IC50 1.0 nM 10.1021/jm010277p
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Neuraminidase IC50 1.4 nM 10.1021/jm0002679
Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1)) Neuraminidase IC50 3.4 nM 10.1016/j.bmcl.2011.09.076
Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1)) Neuraminidase Inhibition nan % 10.1016/j.bmcl.2011.09.076
Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1)) Neuraminidase Ki 0.83 nM 10.1016/j.bmcl.2011.09.076
Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1)) Neuraminidase IC50 0.4 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1)) Neuraminidase IC50 0.48 nM 10.1016/j.ejmech.2017.12.072
Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1)) Neuraminidase T1/2 1.25 hr 10.1128/aac.01681-09
Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1)) Neuraminidase T1/2 24.0 hr 10.1128/aac.01681-09
Influenza B virus Influenza B virus IC50 3.0 nM 10.1128/aac.00474-10
Influenza B virus (strain B/Lee/1940) Neuraminidase IC50 5.0 nM 10.1021/jm010277p
Influenza B virus (strain B/Lee/1940) Neuraminidase IC50 11.0 nM 10.1021/jm0002679
Mus musculus Mus musculus Activity nan None 10.1128/aac.01681-09
Mus musculus Mus musculus Cmax 89.22 nM 10.1128/aac.01681-09
Mus musculus Mus musculus Cmax 53835.15 nM 10.1128/aac.01681-09
Mus musculus Mus musculus Mean day 8.8 None 10.1021/jm0002679
Mus musculus Mus musculus Mean day 9.0 None 10.1021/jm0002679
Mus musculus Mus musculus Survival 1.0 None 10.1021/jm0002679
Mus musculus Mus musculus Survival 7.0 None 10.1021/jm0002679
Mus musculus Mus musculus Survival 9.0 None 10.1021/jm0002679
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 9.502 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 13.19 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.03535 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.06 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.05 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 9.66 % 10.21203/rs.3.rs-23951/v1
unidentified influenza virus unidentified influenza virus Activity nan None 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus IC50 8400.0 nM 10.1016/j.bmc.2008.11.075
unidentified influenza virus unidentified influenza virus Inhibition 0.0 % 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus Inhibition 1.1 % 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus Inhibition 25.8 % 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus Inhibition 36.8 % 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus TIME 125.6 hr 10.1128/aac.00474-10
unidentified influenza virus unidentified influenza virus TIME 169.1 hr 10.1128/aac.00474-10
None ADMET F 2.5 % 10.1016/j.ejmech.2020.112423
None ADMET Ratio CC50/EC50 19.0 None 10.1016/j.ejmech.2021.113929
None Unchecked IC50 0.16 nM 10.1021/acs.jmedchem.2c01258
None Unchecked IC50 2.1 nM 10.1021/jm100621s
None Unchecked IC50 2.8 nM 10.1021/jm100621s
None Unchecked IC50 13.0 nM 10.1021/jm100621s
None Unchecked IC50 14.0 nM 10.1021/jm100621s
None Unchecked IC50 16.7 nM 10.1016/j.ejmech.2017.12.072
None Unchecked IC50 27.8 nM 10.1021/jm100621s
None Unchecked IC50 28.1 nM 10.1021/jm100621s
None Unchecked IC50 41.5 nM 10.1021/jm100621s
None Unchecked IC50 75.2 nM 10.1021/jm100621s
None Unchecked Inhibition nan % 10.1021/acs.jnatprod.8b00656
None Unchecked Ki 0.3 nM 10.1021/jm100621s
None Unchecked Ki 0.6 nM 10.1021/jm100621s
None Unchecked Ki 0.7 nM 10.1021/jm100621s
None Unchecked Ki 1.2 nM 10.1021/jm100621s
None Unchecked Ki 2.3 nM 10.1021/jm100621s
None Unchecked Ki 3.2 nM 10.1021/jm100621s
None Unchecked Ki 8.2 nM 10.1021/jm100621s
None Unchecked Ki 8.3 nM 10.1021/jm100621s
None Unchecked Ratio 50.0 None 10.1021/jm010528u
None Unchecked Ratio 1000.0 None 10.1021/jm010528u
None Unchecked Ratio CC50/EC50 38.0 None 10.1016/j.ejmech.2020.112048
None Unchecked Ratio IC50 1.8 None 10.1021/jm100621s
None Unchecked Ratio IC50 2.0 None 10.1021/jm100621s
None Unchecked Ratio IC50 2.2 None 10.1021/jm100621s
None Unchecked Ratio IC50 2.7 None 10.1021/jm100621s
None Unchecked Ratio IC50 6.2 None 10.1021/jm100621s
None Unchecked Ratio IC50 6.7 None 10.1021/jm100621s
None Unchecked Ratio IC50 9.9 None 10.1021/jm100621s
None Unchecked Ratio IC50 17.3 None 10.1021/jm100621s
None Unchecked Ratio Ki 4.6 None 10.1021/jm100621s
None Unchecked Ratio Ki 6.9 None 10.1021/jm100621s
None Unchecked Ratio Ki 7.7 None 10.1021/jm100621s
None Unchecked Ratio Ki 13.7 None 10.1021/jm100621s

Metabolism Information