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Ligustrazine

AlkaPlorer ID: AK002922

Synonym: None

IUPAC Name: 2,3,5,6-tetramethylpyrazine

Structure

SMILES: CC1=C(C)N=C(C)C(C)=N1

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InChI: InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

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InChIKey: FINHMKGKINIASC-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Theobroma cacao Theobroma Malvaceae Malvales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 136.19799999999998

TPSA？: 25.78

MolLogP？: 1.71028

Number of H-Donors: 0

Number of H-Acceptors: 2

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A549 Activity nan None 10.1021/acs.jmedchem.5b01203
Homo sapiens A549 IC50 15220.0 nM 10.1021/acs.jmedchem.7b01096
Homo sapiens A549 IC50 36460.0 nM 10.1016/j.bmcl.2021.128230
Homo sapiens A549 IC50 200000.0 nM 10.1021/acs.jmedchem.5b01203
Homo sapiens A549/CDDP Activity nan None 10.1021/acs.jmedchem.5b01203
Homo sapiens A549/CDDP IC50 200000.0 nM 10.1021/acs.jmedchem.5b01203
Homo sapiens Bel-7402 IC50 20000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.112.047068
Homo sapiens ECV-304 Activity 10.4 % 10.1016/j.ejmech.2011.09.030
Homo sapiens ECV-304 Activity 12.71 % 10.1016/j.ejmech.2011.09.030
Homo sapiens ECV-304 Activity 22.08 % 10.1016/j.ejmech.2011.09.030
Homo sapiens ECV-304 Activity 42.75 % 10.1016/j.ejmech.2011.09.030
Homo sapiens ECV-304 EC50 154350.0 nM 10.1016/j.bmc.2009.03.012
Homo sapiens ECV-304 EC50 452000.0 nM 10.1016/j.bmc.2007.03.033
Homo sapiens ECV-304 EC50 549000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens ECV-304 EC50 600000.0 nM 10.1016/j.ejmech.2011.09.030
Homo sapiens HCT-116 IC50 8170.0 nM 10.1021/acs.jmedchem.7b01096
Homo sapiens HeLa IC50 20000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens HepG2 IC50 20000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens HepG2 IC50 38250.0 nM 10.1016/j.bmcl.2021.128230
Homo sapiens Histone deacetylase 6 Inhibition -3.53 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 5.19 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens T1/2 2.89 hr 10.1016/j.bmc.2009.03.012
Homo sapiens HT-29 IC50 20000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens HUVEC EC50 600000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens HUVEC EC50 788000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens HUVEC Pmax 20.66 % 10.1016/s0960-894x(03)00359-7
Homo sapiens K562 IC50 5090.0 nM 10.1021/acs.jmedchem.7b01096
Homo sapiens MCF7 IC50 20000.0 nM 10.1016/j.ejmech.2018.01.097
Homo sapiens MCF7 IC50 29850.0 nM 10.1016/j.bmcl.2021.128230
Homo sapiens MDA-MB-231 IC50 20440.0 nM 10.1016/j.bmcl.2021.128230
Homo sapiens SH-SY5Y EC50 17590.0 nM 10.1016/j.ejmech.2019.111695
Homo sapiens Thioredoxin reductase IC50 200000.0 nM 10.1021/acs.jmedchem.5b01203
Homo sapiens U-87 MG IC50 16150.0 nM 10.1021/acs.jmedchem.7b01096
Oryctolagus cuniculus Plasma Activity 3.28 g/L 10.1016/j.bmcl.2019.08.012
Oryctolagus cuniculus Plasma Activity 7.86 % 10.1016/j.bmc.2007.03.033
Oryctolagus cuniculus Plasma APTT 39.24 s 10.1016/j.bmcl.2019.08.012
Oryctolagus cuniculus Plasma PT 6.13 s 10.1016/j.bmcl.2019.08.012
Oryctolagus cuniculus Plasma TT 25.36 s 10.1016/j.bmcl.2019.08.012
Rattus norvegicus PC-12 Activity nan None 10.1016/j.bmcl.2019.08.012
Rattus norvegicus PC-12 EC50 60000.0 nM 10.1016/j.ejmech.2018.01.097
Rattus norvegicus PC-12 EC50 64460.0 nM 10.1016/j.ejmech.2018.01.097
Rattus norvegicus Rattus norvegicus Activity 8.0 % 10.1016/j.bmcl.2016.01.015
Rattus norvegicus Rattus norvegicus Activity 15.0 % 10.1016/j.bmcl.2016.01.015
Rattus norvegicus Rattus norvegicus Activity 16.2 % 10.1016/j.bmcl.2016.01.015
Rattus norvegicus Rattus norvegicus Activity 46.3 % 10.1016/j.bmc.2008.08.075
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.bmcl.2016.01.015
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.bmcl.2019.08.012
Rattus norvegicus Rattus norvegicus Inhibition 50.0 % 10.1016/j.bmc.2008.08.075
Rattus norvegicus Rattus norvegicus Inhibition 71.2 % 10.1016/j.bmc.2008.08.075
Rattus norvegicus Thoracic aorta EC50 2330000.0 nM 10.1016/j.ejmech.2018.01.097
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.86 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 32.16 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.08 % 10.6019/CHEMBL4495565
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 35.14 % 10.21203/rs.3.rs-23951/v1
None Molecular identity unknown Activity nan None 10.1016/j.bmc.2008.08.075
None Neuron Activity 58.4 % 10.1016/j.bmc.2012.04.016
None NON-PROTEIN TARGET Activity 7.86 % 10.1016/j.bmc.2009.03.012
None NON-PROTEIN TARGET Activity 10.4 % 10.1039/C3MD20352B
None NON-PROTEIN TARGET Activity 11.4 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Activity 12.7 % 10.1039/C3MD20352B
None NON-PROTEIN TARGET Activity 13.6 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Activity 22.1 % 10.1039/C3MD20352B
None NON-PROTEIN TARGET Activity 22.1 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Activity 40.9 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Activity 42.8 % 10.1039/C3MD20352B
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmc.2012.04.016
None NON-PROTEIN TARGET EC50 83400.0 nM 10.1039/C4MD00022F
None NON-PROTEIN TARGET EC50 600000.0 nM 10.1039/C3MD20352B
None NON-PROTEIN TARGET IC50 265300.0 nM 10.1039/C4MD00022F
None NON-PROTEIN TARGET Inhibition 3.4 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Inhibition 6.6 % 10.1016/j.bmc.2008.08.075
None NON-PROTEIN TARGET Inhibition 8.6 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Inhibition 9.0 % 10.1016/j.bmc.2008.08.075
None NON-PROTEIN TARGET Inhibition 15.3 % 10.1039/C4MD00022F
None NON-PROTEIN TARGET Inhibition 19.6 % 10.1039/C4MD00022F
None No relevant target LogP 1.26 None 10.1016/j.bmcl.2019.08.012
None No relevant target solubility 4.5 10'3ug/ml 10.1016/j.bmcl.2019.08.012
None Platelet Activity 42.9 % 10.1016/j.bmc.2012.04.016
None Platelet Inhibition 36.2 % 10.1016/j.bmc.2008.08.075
None Radical scavenging activity Activity nan None 10.1016/j.bmc.2012.04.016
None Unchecked EC50 15180.0 nM 10.1016/j.ejmech.2019.111695
None Unchecked Log 1/C nan None 10.1021/jm001129m

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT015267 Cc1nc(C)c(C)nc1C>>CC(=O)N/C(C)=C(/C)NC(C)=O RXN-15015