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4-Aminophenol

AlkaPlorer ID: AK034675

Synonym: p-Hydroxyaniline, Rodinal, Unal, Ursol P 

IUPAC Name: 4-aminophenol

Structure

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

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InChI: InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2

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InChIKey: PLIKAWJENQZMHA-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 109.128

TPSA？: 46.25

MolLogP？: 0.9744

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 31622.8 nM None
Bacillus subtilis Bacillus subtilis IC50 nan nM 10.1021/jm00345a016
Bacillus subtilis Bacillus subtilis Log 1/I50 nan None 10.1021/jm00345a016
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 28183.8 nM None
Homo sapiens Androgen Receptor Potency 44668.4 nM None
Homo sapiens Arachidonate 15-lipoxygenase Potency 25118.9 nM None
Homo sapiens Aryl hydrocarbon receptor Potency 39810.7 nM None
Homo sapiens Beta-glucocerebrosidase Potency 12589.3 nM None
Homo sapiens Bile acid receptor FXR Potency 44668.4 nM None
Homo sapiens Carbonic anhydrase I Ki 159000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase I Ki 159000.0 nM 10.1016/j.bmcl.2008.04.077
Homo sapiens Carbonic anhydrase II Ki 752000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase II Ki 752000.0 nM 10.1016/j.bmcl.2008.04.077
Homo sapiens Carbonic anhydrase III Ki 9500.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase IV Ki 743000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase IX Ki 517000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase VA Ki 867000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase VB Ki 649000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase VI Ki 23500.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase VII Ki 1359000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase XII Ki 479000.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Carbonic anhydrase XIV Ki 10100.0 nM 10.1016/j.bmc.2008.06.013
Homo sapiens Caspase-1 Potency 31622.8 nM None
Homo sapiens Cytochrome P450 3A4 Potency 25118.9 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 35481.3 nM None
Homo sapiens DNA polymerase iota Potency 7079.5 nM None
Homo sapiens DNA polymerase kappa Potency 89125.1 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 3162.3 nM None
Homo sapiens Estrogen receptor alpha Potency 28183.8 nM None
Homo sapiens Eyes absent homolog 2 Potency 19014.8 nM None
Homo sapiens Flap endonuclease 1 Potency 10000.0 nM None
Homo sapiens Glucocorticoid receptor Potency 31622.8 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 12589.3 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 17782.8 nM None
Homo sapiens HepG2 Potency 14125.4 nM None
Homo sapiens Histone acetyltransferase KAT8 IC50 500000.0 nM 10.1016/j.ejmech.2017.05.015
Homo sapiens Histone acetyltransferase p300 IC50 500000.0 nM 10.1016/j.ejmech.2017.05.015
Homo sapiens Histone acetyltransferase PCAF IC50 500000.0 nM 10.1016/j.ejmech.2017.05.015
Homo sapiens HL-60 Activity nan None 10.1039/C2MD20287E
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 50118.7 nM None
Homo sapiens Lymphoblastoid cell Potency 25118.9 nM None
Homo sapiens Lymphoblastoid cell Potency 31622.8 nM None
Homo sapiens Lymphoblastoid cell Potency 39810.7 nM None
Homo sapiens Lymphoblastoid cell Potency 50118.7 nM None
Homo sapiens Lymphoblastoid cell Potency 63095.7 nM None
Homo sapiens Lymphoblastoid cell Potency 79432.8 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 10000.0 nM None
Homo sapiens MIA PaCa-2 IC50 41979.0 nM 10.1021/jm070396q
Homo sapiens MIA PaCa-2 IC50 42250.0 nM 10.1021/jm070396q
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 4466.8 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 26603.2 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 35481.3 nM None
Homo sapiens Nuclear receptor ROR-gamma Potency 42163.2 nM None
Homo sapiens Peroxisome proliferator-activated receptor delta Potency 17782.8 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma Potency 17782.8 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 44668.4 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 12589.3 nM None
Homo sapiens Thyroid hormone receptor beta-1 Potency 35481.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 6309.6 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 7695.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 12197.2 nM None
Homo sapiens UDP-glucuronosyltransferase 1-6 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-9 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1A4 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B17 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens Vitamin D receptor Potency 79432.8 nM None
Mus musculus Anandamide amidohydrolase Drug metabolism 8.8 nmol 10.1016/j.ejmech.2020.113042
Mus musculus Carbonic anhydrase 15 Ki 335000.0 nM 10.1016/j.bmcl.2008.04.077
Mus musculus Carbonic anhydrase XIII Ki 657000.0 nM 10.1016/j.bmc.2008.06.013
Mus musculus Mus musculus Activity 44.0 % 10.1016/j.ejmech.2020.113042
Mus musculus Mus musculus Activity 60.0 % 10.1016/j.ejmech.2020.113042
Mus musculus Mus musculus Activity 81.0 % 10.1016/j.ejmech.2020.113042
Mus musculus Mus musculus Activity nan None 10.1016/j.ejmech.2020.113042
Mus musculus Mus musculus Ratio 1.0 None 10.1016/j.ejmech.2020.113042
Mus musculus Nuclear receptor ROR-gamma Potency 17782.8 nM None
Mycobacterium tuberculosis Protein RecA EC50 380000.0 nM None
Mycobacterium tuberculosis Replicative DNA helicase AC50 40600.0 nM None
Mycobacterium tuberculosis Replicative DNA helicase AC50 380000.0 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 12817.8 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 33161.6 nM None
Rattus norvegicus Rattus norvegicus Activity 63.0 % 10.1021/jm00187a016
Rattus norvegicus Rattus norvegicus Activity 73.0 % 10.1021/jm00187a016
Rattus norvegicus Rattus norvegicus Selectivity ratio 1.04 None 10.1021/jm00187a016
Rattus norvegicus Rattus norvegicus T/C 0.94 None 10.1021/jm00187a016
Rattus norvegicus Rattus norvegicus T/C 0.98 None 10.1021/jm00187a016
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 8912.5 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 14125.4 nM None
Trypanosoma cruzi Cruzipain Potency 31622.8 nM None
None ADMET Activity nan None 10.1016/j.ejmech.2020.113042
None ADMET Drug metabolism 0.05 nmol 10.1016/j.ejmech.2020.113042
None ADMET Drug metabolism 24.0 pmol 10.1016/j.ejmech.2020.113042
None ADMET Drug metabolism 1002.0 pmol 10.1016/j.ejmech.2020.113042
None Hepatotoxicity Hepatotoxicity nan None 10.1124/dmd.110.035113
None Molecular identity unknown Potency 33491.5 nM None
None Molecular identity unknown Potency 35481.3 nM None
None No relevant target EC50 20000.0 nM 10.1016/j.ejmech.2017.05.015
None No relevant target LogD 0.04 None 10.1021/jm00345a016
None No relevant target LogP 0.04 None 10.1021/jm00345a016
None No relevant target pKa 10.3 None 10.1021/jm00345a016
None Radical scavenging activity Activity 310.0 10'3/M/s 10.1039/C2MD20287E
None Unchecked Ac50 4.467 uM None
None Unchecked Ac50 8.913 uM None
None Unchecked AC50 4466.8 nM None
None Unchecked AC50 8912.5 nM None
None Unchecked EC50 18530.0 nM None
None Unchecked IC50 10000.0 nM None
None Unchecked IC50 47656.0 nM None
None Unchecked IC50 70570.0 nM None
None Unchecked IC50 70980.0 nM None
None Unchecked IC50 83000.0 nM 10.1016/j.bmc.2010.01.002
None Unchecked IC50 90000.0 nM 10.1016/j.bmc.2010.01.002
None Unchecked Inhibition 64.0 % 10.1016/j.bmc.2012.09.040
None Unchecked Ki 32000.0 nM 10.1016/j.bmc.2017.03.026
None Unchecked Potency 6682.4 nM None
None Unchecked Potency 7497.8 nM None
None Unchecked Potency 11997.5 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 31622.8 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Potency 44668.4 nM None
None Unchecked Potency 50118.7 nM None
None Unchecked Ratio Ki 3.12 None 10.1016/j.bmc.2017.03.026

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004036 CC(=O)Nc1ccc(O)cc1>>CC(=O)O.Nc1ccc(O)cc1 None
AKRT004037 CC(=O)Nc1ccc(O)cc1>>Nc1ccc(O)cc1 RXN-19419
AKRT004097 CC(=O)O.Nc1ccc(O)cc1>>CC(=O)Nc1ccc(O)cc1 enzymemap_76309
AKRT004739 CC(=O)[CoA].Nc1ccc(O)cc1>>CC(=O)Nc1ccc(O)cc1 enzymemap_28552
AKRT005891 CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)Oc1ccc(N)cc1>>Nc1ccc(O)cc1 enzymemap_71238
AKRT007581 CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)Nc1ccc(O)cc1>>Nc1ccc(O)cc1 enzymemap_77400
AKRT009765 CCOP(=S)(OCC)Oc1ccc(N)cc1>>Nc1ccc(O)cc1 R05485
AKRT014368 C[N+](C)(C)CCOP(=O)(O)Oc1ccc(N)cc1>>Nc1ccc(O)cc1 enzymemap_57496
AKRT015395 Cc1ncc(C[n+]2csc(CCO)c2C)c(=N)[nH]1.Nc1ccc(O)cc1>>Cc1ncc(CNc2ccc(O)cc2)c(=N)[nH]1 enzymemap_40275
AKRT018994 N[C@@H](CCC(=O)Nc1ccc(O)cc1)C(=O)O>>Nc1ccc(O)cc1 enzymemap_33425
AKRT020616 Nc1ccc(C(=O)O)cc1>>Nc1ccc(O)cc1 4-AMINOBENZOATE-1-MONOOXYGENASE-RXN
AKRT020642 Nc1ccc(O)cc1.O=C=O>>Nc1ccc(C(=O)O)cc1 enzymemap_12306
AKRT020643 Nc1ccc(O)cc1>>Nc1ccc(OS(=O)(=O)O)cc1 enzymemap_50241
AKRT020644 Nc1ccc(O)cc1>>Nc1ccccc1 MNXR172058
AKRT020645 Nc1ccc(O)cc1>>O=C1C=CC(=O)C=C1 R06852
AKRT020646 Nc1ccc(O)cc1>>O=[N+](O)c1ccc(O)cc1 RXN-22382
AKRT020647 Nc1ccc(O)cc1>>Oc1ccc(O)cc1 RXN-13560
AKRT020655 Nc1ccc(OP(=O)(O)O)cc1>>Nc1ccc(O)cc1 enzymemap_55253
AKRT020656 Nc1ccc(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1>>Nc1ccc(O)cc1 enzymemap_60599
AKRT020657 Nc1ccc(O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)cc1>>Nc1ccc(O)cc1 enzymemap_61211
AKRT024854 ONc1ccccc1>>Nc1ccc(O)cc1 enzymemap_88280