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name Structure Reference Source Properties Activities Metabolism

Aminohippuric Acid

AlkaPlorer ID: AK020563

Synonym: None

IUPAC Name: 2-[(4-aminobenzoyl)amino]acetic acid

Structure

SMILES: NC1=CC=C(C(=O)NCC(=O)O)C=C1

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InChI: InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)

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InChIKey: HSMNQINEKMPTIC-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 194.19000000000003

TPSA？: 92.42

MolLogP？: 0.0831999999999996

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli K-12 Beta-lactamase AmpC Potency 5623.4 nM None
Homo sapiens 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase Activity 5.03 % 10.1021/acs.jmedchem.0c01762
Homo sapiens 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase Activity 95.0 % 10.1021/acs.jmedchem.0c01762
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 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 Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.112.047068
Homo sapiens Canalicular multispecific organic anion transporter 1 Activity 46.0 % 10.1021/jm7015683
Homo sapiens Canalicular multispecific organic anion transporter 1 Km 880000.0 nM 10.1046/j.1523-1755.2000.00007.x
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Dopamine D1 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 30000.0 nM 10.1038/s41467-023-40064-9
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 19952.6 nM None
Homo sapiens HERG 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 -6.43 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 6.74 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 5011.9 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 31622.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 28183.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 31622.8 nM None
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Multidrug resistance-associated protein 1 Km 372000.0 nM 10.1046/j.1523-1755.2000.00007.x
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 Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens P-glycoprotein 1 Activity nan None 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 Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 141.3 nM None
Homo sapiens Serotonin 1a (5-HT1a) 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 transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier family 22 member 11 Activity nan None 10.1016/s0167-4889(02)00187-8
Homo sapiens Solute carrier family 22 member 11 Activity nan None 10.1074/jbc.275.6.4507
Homo sapiens Solute carrier family 22 member 4 Activity nan None None
Homo sapiens Solute carrier family 22 member 5 Activity nan None None
Homo sapiens Solute carrier family 22 member 6 Activity 400.0 pmol/min/mg 10.1016/j.bmc.2019.07.012
Homo sapiens Solute carrier family 22 member 6 Activity nan None 10.1038/nrd3028
Homo sapiens Solute carrier family 22 member 6 Activity nan None 10.1152/ajprenal.00140.2003
Homo sapiens Solute carrier family 22 member 6 FC 3.5 None 10.1124/dmd.111.042036
Homo sapiens Solute carrier family 22 member 6 IC50 8800.0 nM 10.1006/abio.2000.4633
Homo sapiens Solute carrier family 22 member 6 IC50 127000.0 nM 10.1046/j.1523-1755.2003.00710.x
Homo sapiens Solute carrier family 22 member 6 Jmax 230.0 pmol/min 10.1124/dmd.111.042036
Homo sapiens Solute carrier family 22 member 6 Ki 6020.0 nM 10.1016/j.bmc.2011.04.045
Homo sapiens Solute carrier family 22 member 6 Ki 6020.0 nM 10.1016/s0024-3205(01)01296-6
Homo sapiens Solute carrier family 22 member 6 Km 3900.0 nM None
Homo sapiens Solute carrier family 22 member 6 Km 4000.0 nM 10.1124/mol.56.3.570
Homo sapiens Solute carrier family 22 member 6 Km 5000.0 nM 10.1152/ajprenal.1999.276.2.f295
Homo sapiens Solute carrier family 22 member 6 Km 8500.0 nM 10.1152/ajprenal.00140.2003
Homo sapiens Solute carrier family 22 member 6 Km 8900.0 nM 10.1124/jpet.102.043455
Homo sapiens Solute carrier family 22 member 6 Km 9300.0 nM 10.1152/ajprenal.1999.276.1.f122
Homo sapiens Solute carrier family 22 member 6 Km 15400.0 nM 10.1681/asn.v113383
Homo sapiens Solute carrier family 22 member 6 Km 20000.0 nM 10.1124/dmd.111.042036
Homo sapiens Solute carrier family 22 member 6 Km 22000.0 nM 10.1038/sj.bjp.0704482
Homo sapiens Solute carrier family 22 member 6 Ratio 11.0 uL/min 10.1124/dmd.111.042036
Homo sapiens Solute carrier family 22 member 7 Activity nan None 10.1006/bbrc.2001.4774
Homo sapiens Solute carrier family 22 member 8 Activity nan None 10.1006/bbrc.1998.9978
Homo sapiens Solute carrier family 22 member 8 Activity nan None 10.1159/000074539
Homo sapiens Solute carrier family 22 member 8 Ki 19600.0 nM 10.1016/s0024-3205(01)01296-6
Homo sapiens Solute carrier family 22 member 8 Km 87200.0 nM 10.1124/mol.59.5.1277
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1211/0022357021440
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 30.1 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 82.43 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 23.7 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 94.72 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 27.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 3A1 Activity 30.0 % 10.1152/ajprenal.00402.2002
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
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Mus musculus Solute carrier family 22 member 20 Ki 446000.0 nM 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 20 Ki 446683.59 nM 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 20 Vmax 4.6 pmol/hr 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 5 Activity nan None 10.1124/mol.59.2.358
Mus musculus Solute carrier family 22 member 6 Ki 9332.54 nM 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 6 Ki 9400.0 nM 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 6 Km 37300.0 nM 10.1074/jbc.274.3.1519
Mus musculus Solute carrier family 22 member 6 Vmax 5.7 pmol/hr 10.1074/jbc.m703467200
Mus musculus Solute carrier family 22 member 7 Activity nan None 10.1124/mol.62.1.7
Mus musculus Solute carrier family 22 member 8 Activity 14.2 % 10.1124/jpet.103.063370
Mus musculus Solute carrier family 22 member 8 Activity 20.0 % 10.1124/dmd.32.5.479
Mus musculus Solute carrier family 22 member 8 Activity nan None 10.1074/jbc.m203803200
Mus musculus Solute carrier family 22 member 8 Activity nan None 10.1124/dmd.32.5.479
Mus musculus Solute carrier family 22 member 8 Activity nan None 10.1124/jpet.103.063370
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Plasmodium falciparum Plasmodium falciparum Potency 11689.1 nM None
Rattus norvegicus Aldose reductase IC50 nan nM 10.1021/jm00125a017
Rattus norvegicus Aldose reductase Inhibition 22.0 % 10.1021/jm00125a017
Rattus norvegicus Monocarboxylate transporter 1 Activity nan None 10.1211/0022357991776804
Rattus norvegicus Peptidyl-glycine alpha-amidating monooxygenase Activity 0.4 None 10.1016/j.bmc.2008.10.013
Rattus norvegicus Peptidyl-glycine alpha-amidating monooxygenase Km 2600000.0 nM 10.1016/j.bmc.2008.10.013
Rattus norvegicus Peptidyl-glycine alpha-amidating monooxygenase Ratio 2.2 10'3/M/s 10.1016/j.bmc.2008.10.013
Rattus norvegicus Peptidyl-glycine alpha-amidating monooxygenase Vmax(app) 5.6 /s 10.1016/j.bmc.2008.10.013
Rattus norvegicus Solute carrier family 22 member 1 Activity nan None 10.1074/jbc.272.26.16548
Rattus norvegicus Solute carrier family 22 member 1 IC50 1300000.0 nM 10.1152/ajprenal.2001.281.3.f454
Rattus norvegicus Solute carrier family 22 member 2 IC50 4500000.0 nM 10.1152/ajprenal.2001.281.3.f454
Rattus norvegicus Solute carrier family 22 member 6 Activity nan None 10.1124/mol.60.5.1091
Rattus norvegicus Solute carrier family 22 member 6 Activity nan None None
Rattus norvegicus Solute carrier family 22 member 6 Km 14300.0 nM 10.1074/jbc.272.30.18526
Rattus norvegicus Solute carrier family 22 member 6 Km 31000.0 nM None
Rattus norvegicus Solute carrier family 22 member 6 Km 43200.0 nM 10.1046/j.1523-1755.1999.00789.x
Rattus norvegicus Solute carrier family 22 member 6 Km 70000.0 nM 10.1074/jbc.272.48.30088
Rattus norvegicus Solute carrier family 22 member 6 Km 85100.0 nM None
Rattus norvegicus Solute carrier family 22 member 7 Activity nan None 10.1016/s0014-5793(98)00585-7
Rattus norvegicus Solute carrier family 22 member 8 Activity 20.3 % 10.1097/00004647-200304000-00007
Rattus norvegicus Solute carrier family 22 member 8 Ki 301000.0 nM None
Rattus norvegicus Solute carrier family 22 member 8 Ki 398000.0 nM 10.1124/mol.61.5.982
Rattus norvegicus Solute carrier family 22 member 8 Ki 1350000.0 nM 10.1124/jpet.300.3.746
Rattus norvegicus Solute carrier family 22 member 8 Km 64700.0 nM 10.1074/jbc.274.19.13675
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Activity nan None 10.1152/ajprenal.1996.270.2.f319
Rattus norvegicus Solute carrier organic anion transporter family member 1A3 Activity nan None 10.1016/s0014-5793(99)01221-1
Rattus norvegicus Solute carrier organic anion transporter family member 1A4 Activity nan None 10.1007/s004240100697
Rattus norvegicus Solute carrier organic anion transporter family member 1A5 Activity nan None 10.1007/s004240100697
Rattus norvegicus Solute carrier organic anion transporter family member 1B2 Activity nan None 10.1007/s004240100697
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 16.91 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.08913 None 10.1101/2020.04.21.054387
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 -0.2 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 3.54 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.2473 None 10.1101/2020.04.03.023846
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 0.0 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 0.0 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 Unchecked Ac50 0.631 uM None
None Unchecked Ac50 1.259 uM None
None Unchecked AC50 631.0 nM None
None Unchecked AC50 1258.9 nM None
None Unchecked Inhibition_index 260.0 None 10.1021/jm00212a009
None Unchecked Ratio 7.0 None 10.1016/j.bmc.2019.07.012
None Unchecked Ratio pKi -1.68 None 10.1074/jbc.m703467200

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT017669 NCC(=O)O.Nc1ccc(C(=O)[32S])cc1>>Nc1ccc(C(=O)NCC(=O)O)cc1 None
AKRT020623 Nc1ccc(C(=O)[CoA])cc1.NCC(=O)O>>Nc1ccc(C(=O)NCC(=O)O)cc1 enzymemap_31739