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Ephedrine

AlkaPlorer ID: AK003599

Synonym: None

IUPAC Name: (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol

Structure

SMILES: CN[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/t8-,10+/m0/s1

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InChIKey: KWGRBVOPPLSCSI-WCBMZHEXSA-N

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Properties Information

Molecule Weight: 165.236

TPSA？: 32.26

MolLogP？: 1.3279

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 12.6 nM None
Cryptosporidium parvum Cryptosporidium parvum IC50 nan None 10.1016/j.bmc.2010.01.068
Entamoeba histolytica Entamoeba histolytica IC50 nan None 10.1016/j.bmc.2010.01.068
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-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 12999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-galactosidase A Potency 25118.9 nM None
Homo sapiens Alpha-galactosidase A Potency 39810.7 nM None
Homo sapiens Arachidonate 12-lipoxygenase Potency 3162.3 nM None
Homo sapiens Arachidonate 15-lipoxygenase Potency 398.1 nM None
Homo sapiens Arachidonate 15-lipoxygenase, type II Potency 631.0 nM None
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-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 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 Cytochrome P450 2C19 Potency 1584.9 nM None
Homo sapiens Cytochrome P450 2C9 Potency 794.3 nM None
Homo sapiens Cytochrome P450 2D6 Potency 12589.3 nM None
Homo sapiens Cytochrome P450 3A4 Potency 19952.6 nM None
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 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 631.0 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 1584.9 nM None
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 Guanine nucleotide-binding protein G(i) subunit alpha-1/Regulator of G-protein signaling 12 Potency 7943.3 nM None
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 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 Vdss 2.84 L.kg-1 10.1016/j.ejmech.2009.06.004
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 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 Nuclear factor NF-kappa-B p105 subunit Potency 28183.8 nM None
Homo sapiens Phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase 1 Inhibition 2.0 % 10.1016/j.bmcl.2015.09.034
Homo sapiens Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 Inhibition 13.0 % 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 Pyruvate kinase isozymes M1/M2 Potency 7943.3 nM None
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 1624.7 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 Thrombopoietin Potency 3162.3 nM None
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thyroid stimulating hormone receptor Potency 125.9 nM None
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
Leishmania amazonensis Leishmania amazonensis IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania donovani Leishmania donovani IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania infantum Leishmania infantum IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania major Leishmania major IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania mexicana Leishmania mexicana IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania mexicana Pyruvate kinase Potency 10000.0 nM None
Mus musculus Monoamine oxidase A Activity nan None 10.1021/jm800656v
Photinus pyralis Luciferin 4-monooxygenase Potency 39810.7 nM None
Plasmodium falciparum Plasmodium falciparum IC50 nan None 10.1016/j.bmc.2010.01.068
Pneumocystis carinii Pneumocystis carinii IC50 nan None 10.1016/j.bmc.2010.01.068
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 Plasma logFu 1.0 None 10.1016/j.ejmech.2009.06.004
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
Toxoplasma gondii Toxoplasma gondii IC50 nan None 10.1016/j.bmc.2010.01.068
Trichomonas vaginalis Trichomonas vaginalis IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei Trypanosoma brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma cruzi Trypanosoma cruzi IC50 nan None 10.1016/j.bmc.2010.01.068
None NON-PROTEIN TARGET IC50 nan None 10.1016/j.bmc.2010.01.068
None No relevant target log K 0.13 None 10.1021/jm9003945
None No relevant target log K 0.59 None 10.1021/jm9003945
None No relevant target LogP 0.89 None 10.1021/jm9003945
None No relevant target pKa 9.86 None 10.1016/j.ejmech.2009.06.004
None No relevant target pKa 10.25 None 10.1021/jm9003945
None No relevant target solubility nan None 10.1016/j.bmc.2010.08.003
None Phospholipidosis Phospholipidosis nan None 10.1080/15376510701857262

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010785 CN[C@@H](C)C(=O)c1ccccc1>>CN[C@@H](C)[C@@H](O)c1ccccc1 RXN-21135
AKRT010788 CN[C@@H](C)[C@@H](O)c1ccccc1.C[SAH]>>C[C@@H]([C@@H](O)c1ccccc1)N(C)C RXN-21529
AKRT010789 CN[C@@H](C)[C@@H](O)c1ccccc1>>CN=C(C)C(O)c1ccccc1 enzymemap_22894
AKRT010790 CN[C@@H](C)[C@@H](O)c1ccccc1>>CN[C@@H](C)C(=O)c1ccccc1 enzymemap_5008
AKRT014581 C[SAH].C[C@H](N)[C@@H](O)c1ccccc1>>CN[C@@H](C)[C@@H](O)c1ccccc1 R08465