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name Structure Reference Source Properties Activities Metabolism

7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

AlkaPlorer ID: AK018762

Synonym: None

IUPAC Name: (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Structure

SMILES: CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)[C@H]2SC1

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InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1

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InChIKey: BOEGTKLJZSQCCD-UEKVPHQBSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Apis cerana Apis Apidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota

Properties Information

Molecule Weight: 363.3950000000001

TPSA？: 132.96

MolLogP？: 0.150500000000001

Number of H-Donors: 4

Number of H-Acceptors: 6

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli Escherichia coli Activity nan None 10.1128/aac.00014-10
Escherichia coli Escherichia coli Inhibition nan % 10.1128/aac.00014-10
Homo sapiens 5637 Activity nan None 10.1128/aac.00014-10
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens ATP-binding cassette sub-family G member 2 Drug transport nan None 10.1124/dmd.111.041731
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump AC50 300000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 1 Activity 68.0 % 10.1021/jm7015683
Homo sapiens Canalicular multispecific organic anion transporter 1 Drug transport nan None 10.1124/dmd.111.041731
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 1 Inhibition nan % 10.1124/dmd.111.041731
Homo sapiens Canalicular multispecific organic anion transporter 2 Activity nan None 10.1124/dmd.111.041731
Homo sapiens Canalicular multispecific organic anion transporter 2 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 2 Inhibition nan % 10.1124/dmd.111.041731
Homo sapiens Canalicular multispecific organic anion transporter 2 Km 2500000.0 nM 10.1124/dmd.111.041731
Homo sapiens Canalicular multispecific organic anion transporter 2 Vmax 0.6 nmol/min 10.1124/dmd.111.041731
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 21000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Galactocerebrosidase Potency 631.0 nM None
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Geminin Potency 163.6 nM None
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -42.57 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -0.57 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens Activity 1.0 % 10.1016/j.ejmech.2009.11.034
Homo sapiens Homo sapiens CL 0.2 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens CL 2.5 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens CL 2.5 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens CL_renal 2.3 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens CL_renal 2.33 mL.min-1.kg-1 10.1021/jm900403j
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 7.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens Fa 1.0 None 10.1021/jm901371v
Homo sapiens Homo sapiens F_fraction 0.95 None 10.1021/jm901371v
Homo sapiens Homo sapiens Fg 0.96 None 10.1021/jm901371v
Homo sapiens Homo sapiens Fh 0.99 None 10.1021/jm901371v
Homo sapiens Homo sapiens Vdss 0.23 L.kg-1 10.1021/jm901371v
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Multidrug resistance-associated protein 1 Activity nan None 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 1 Km 3900000.0 nM 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 1 Vmax 12.4 nmol/min 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 4 Activity nan None 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 4 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Multidrug resistance-associated protein 4 Inhibition nan % 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 4 Km 250000.0 nM 10.1124/dmd.111.041731
Homo sapiens Multidrug resistance-associated protein 4 Vmax 1.2 nmol/min 10.1124/dmd.111.041731
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Oligopeptide transporter small intestine isoform Activity 27.0 % 10.1074/jbc.270.12.6456
Homo sapiens Oligopeptide transporter small intestine isoform Activity nan None 10.1006/bbrc.1998.9298
Homo sapiens Oligopeptide transporter small intestine isoform Activity nan None 10.1038/nrd3028
Homo sapiens Oligopeptide transporter small intestine isoform Activity nan None 10.2133/dmpk.17.253
Homo sapiens Oligopeptide transporter small intestine isoform IC50 870000.0 nM 10.1074/jbc.270.43.25672
Homo sapiens Oligopeptide transporter small intestine isoform IC50 5400000.0 nM 10.1074/jbc.270.43.25672
Homo sapiens Oligopeptide transporter small intestine isoform Ki 1450000.0 nM None
Homo sapiens Oligopeptide transporter small intestine isoform Ki 7200000.0 nM 10.1016/j.ejpb.2004.07.008
Homo sapiens Oligopeptide transporter small intestine isoform Ki 7200000.0 nM 10.1021/jm048982w
Homo sapiens Oligopeptide transporter small intestine isoform Ki 9100000.0 nM None
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier family 15 member 2 Activity 0.0 % 10.1016/0005-2736(95)80036-f
Homo sapiens Solute carrier family 15 member 2 Activity nan None 10.1038/nrd3028
Homo sapiens Solute carrier family 15 member 2 IC50 66000.0 nM 10.1074/jbc.270.43.25672
Homo sapiens Solute carrier family 15 member 2 Ki 2500.0 nM 10.1074/jbc.270.43.25672
Homo sapiens Solute carrier family 15 member 2 Ki 2800.0 nM 10.1074/jbc.270.43.25672
Homo sapiens Solute carrier family 15 member 2 Ki 3000.0 nM 10.1016/j.bmc.2011.06.027
Homo sapiens Solute carrier family 15 member 2 Ki 3019.95 nM 10.1016/j.bmc.2011.06.027
Homo sapiens Solute carrier family 22 member 5 Activity nan None 10.1074/jbc.275.3.1699
Homo sapiens Solute carrier family 22 member 6 Ki 6140.0 nM 10.1016/s0014-2999(02)01306-7
Homo sapiens Solute carrier family 22 member 8 Inhibition 20.0 % 10.1124/dmd.112.049569
Homo sapiens Solute carrier family 22 member 8 Ki 8620.0 nM 10.1016/s0014-2999(02)01306-7
Homo sapiens Solute carrier family 22 member 8 Ki 8620.0 nM 10.1124/dmd.112.049569
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 9.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 88.52 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 21.0 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 101.2 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 3.5 % 10.1021/jm300212s
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Mus musculus Intestine Drug uptake nan None 10.1124/dmd.111.041731
Mus musculus Jejunum Drug transport 50.0 % 10.1124/dmd.111.041731
Mus musculus Jejunum Drug transport nan None 10.1124/dmd.111.041731
Mus musculus Kidney Drug uptake nan None 10.1124/dmd.111.041731
Mus musculus Liver Drug uptake nan None 10.1124/dmd.111.041731
Mus musculus Solute carrier family 22 member 6 Inhibition nan % 10.1124/dmd.112.049569
Mus musculus Solute carrier family 22 member 8 Inhibition nan % 10.1124/dmd.112.049569
Mus musculus Solute carrier family 22 member 8 PPB nan % 10.1124/dmd.112.049569
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 23000.1 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Oligopeptide transporter, kidney isoform Ki 3000.0 nM 10.1016/j.ejpb.2004.07.008
Rattus norvegicus Oligopeptide transporter, kidney isoform Ki 3000.0 nM 10.1152/ajprenal.1997.273.5.f706
Rattus norvegicus Plasma Fu 0.39 None 10.1021/jm901371v
Rattus norvegicus Solute carrier family 15 member 1 Activity nan None 10.1111/j.2042-7158.1997.tb06115.x
Rattus norvegicus Solute carrier family 15 member 1 Ki 2170000.0 nM 10.1152/ajprenal.1997.273.5.f706
Rattus norvegicus Solute carrier family 22 member 5 Activity nan None 10.1074/jbc.275.3.1699
Rattus norvegicus Solute carrier family 22 member 6 Activity nan None None
Rattus norvegicus Solute carrier family 22 member 6 IC50 2000000.0 nM 10.1016/s0024-3205(02)01500-x
Rattus norvegicus Solute carrier family 22 member 8 IC50 1780000.0 nM 10.1016/s0024-3205(02)01500-x
Rattus norvegicus Solute carrier family 22 member 8 IC50 1780000.0 nM 10.1124/dmd.112.049569
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 14.01 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.046 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.07 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 31.91 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.02715 None 10.1101/2020.04.03.023846
Staphylococcus aureus Staphylococcus aureus IC50 312.0 ug.mL-1 10.1016/j.bmcl.2012.07.016
None ADMET CL 2.5 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET CL 3.0 uL.min-1.(10^6cells)-1 10.6019/CHEMBL3301361
None ADMET Drug excretion nan None 10.1124/dmd.111.041731
None ADMET Drug uptake 0.4 % 10.1124/dmd.111.041731
None ADMET MRT 1.5 hr 10.1124/dmd.108.020479
None ADMET Ratio 3.0 None 10.1124/dmd.111.041731
None ADMET Ratio 6.0 None 10.1124/dmd.111.041731
None ADMET T1/2 1.1 hr 10.1124/dmd.108.020479
None ADMET Vdss 0.23 L.kg-1 10.1124/dmd.108.020479
None Hepatotoxicity Alkaline Phosphatase Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Active 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Marginal 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx1000865
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None Hepatotoxicity Hepatotoxicity nan None 10.1124/dmd.110.035113
None Hepatotoxicity HepSE_bilirubinemia 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholecystitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholelithiasis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cirrhosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_Combined Scores 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic failure 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic necrosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatomegaly 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_jaundice 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver disease 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver fatty 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver function tests abnormal 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity LDH Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None NON-PROTEIN TARGET Fu 0.39 None 10.1124/dmd.108.020479
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 1.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 3.1 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None No relevant target LogD7.4 -0.86 None 10.6019/CHEMBL3301361
None Unchecked Ac50 0.3162 uM None
None Unchecked Ac50 5.012 uM None
None Unchecked Ac50 6.31 uM None
None Unchecked Ac50 8.913 uM None
None Unchecked Ac50 39.81 uM None
None Unchecked AC50 316.2 nM None
None Unchecked AC50 5011.9 nM None
None Unchecked AC50 6309.6 nM None
None Unchecked AC50 8912.5 nM None
None Unchecked AC50 39820.0 nM None
None Unchecked Hepatotoxicity (acute) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Potency 15848.9 nM None

Metabolism Information