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Pseudoephedrine

AlkaPlorer ID: AK003598

Synonym: None

IUPAC Name: [(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-methylazanium

Structure

SMILES: C[NH2+][C@@H](C)[C@H](O)C1=CC=CC=C1

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InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/p+1/t8-,10-/m0/s1

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InChIKey: KWGRBVOPPLSCSI-WPRPVWTQSA-O

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Properties Information

Molecule Weight: 166.244

TPSA？: 36.84

MolLogP？: 0.3017000000000001

Number of H-Donors: 2

Number of H-Acceptors: 1

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Canis lupus familiaris Canis familiaris Activity 40.0 mmHg 10.1021/jm00223a011
Canis lupus familiaris Canis familiaris Activity nan None 10.1021/jm00223a011
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 12999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-1 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-3 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin B receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Corticotropin releasing factor receptor 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Corticotropin releasing factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D4 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-B AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 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 Estrogen receptor beta AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gastric inhibitory polypeptide receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucagon receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -44.73 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -8.69 % 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 Homo sapiens log Kp -5.75 cm/s 10.1021/jm060230+
Homo sapiens Hydroxycarboxylic acid receptor 2 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Kappa opioid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 17000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neurokinin 1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neurotensin receptor 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase 1 Inhibition 0.0 % 10.1016/j.bmcl.2015.09.034
Homo sapiens Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 Inhibition 0.0 % 10.1016/j.bmcl.2015.09.034
Homo sapiens Phosphodiesterase 3A 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 10000.0 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 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Skin log Kp -5.78 None 10.1016/j.bmc.2007.07.050
Homo sapiens Skin log Kp -5.75 None 10.1021/jm0611105
Homo sapiens Sodium channel protein type V alpha subunit 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 Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V1a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Whole blood Retention_time 2.28 min 10.1007/s00044-012-9977-1
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Colon log%Abs 0.95 None 10.1021/jm00211a010
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Rattus norvegicus ED50 0.8 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 13.1 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Small intestine log%Abs 0.85 None 10.1021/jm00211a010
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Voltage-gated N-type calcium channel alpha-1B subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
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
None ADMET Activity 1.0 % 10.1021/jm060230+
None ADMET Activity 21.8 % 10.1021/jm060230+
None ADMET log Pe -4.82 cm/s 10.1021/jm060230+
None ADMET log Pe -4.81 None 10.1021/jm0611105
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None No relevant target LogD -2.74 None 10.1021/jm00211a010
None No relevant target LogD7.4 -1.15 None 10.6019/CHEMBL3301361
None No relevant target LogP 0.93 None 10.1021/jm0611105
None No relevant target LogP 1.56 None 10.1021/jm00211a010
None No relevant target LogP 19.0 None 10.1021/jm00379a002
None No relevant target Log PNalk -0.77 None 10.1021/jm048980b
None No relevant target Log S -0.47 None 10.1016/s0960-894x(00)00172-4
None No relevant target pKa 2.8 None 10.1021/jm00211a010
None No relevant target pKa 4.3 None 10.1021/jm00211a010
None No relevant target pKa 9.61 None 10.1007/s11095-013-1232-z
None No relevant target pKa 9.65 None 10.1007/s11095-013-1232-z
None No relevant target pKa 9.65 None 10.1021/jm060230+
None No relevant target solubility nan None 10.1016/j.bmc.2010.08.003
None Phospholipidosis Phospholipidosis nan None 10.1080/15376510701857262
None Unchecked -Log KD -1.22 None 10.1021/jm00354a004
None Unchecked Potency 446.7 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010786 CN[C@@H](C)C(=O)c1ccccc1>>CN[C@@H](C)[C@H](O)c1ccccc1 RXN-21134
AKRT010791 CN[C@@H](C)[C@H](O)c1ccccc1.C[SAH]>>C[C@@H]([C@H](O)c1ccccc1)N(C)C RXN-21528
AKRT010792 CN[C@@H](C)[C@H](O)c1ccccc1>>C/N=C(\C)[C@H](O)c1ccccc1 R03614
AKRT010793 CN[C@@H](C)[C@H](O)c1ccccc1>>CNC(C)C(OS(=O)(=O)O)c1ccccc1 enzymemap_49981
AKRT010794 CN[C@@H](C)[C@H](O)c1ccccc1>>CN[C@@H](C)C(=O)c1ccccc1 enzymemap_5027
AKRT014572 C[SAH].C[C@@H](N)[C@@H](O)c1ccccc1>>CN[C@@H](C)[C@H](O)c1ccccc1 MNXR150281
AKRT014582 C[SAH].C[C@H](N)[C@H](O)c1ccccc1>>CN[C@@H](C)[C@H](O)c1ccccc1 RXN-9341