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Vincamine

AlkaPlorer ID: AK004148

Synonym: None

IUPAC Name: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

Structure

SMILES: CC[C@@]12CCCN3CCC4=C([C@@H]31)N(C1=CC=CC=C41)[C@@](O)(C(=O)OC)C2

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InChI: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

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InChIKey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

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Properties Information

Molecule Weight: 354.45000000000016

TPSA？: 54.7

MolLogP？: 2.952500000000001

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 7.29 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 3.22 % 10.1016/j.bmc.2012.09.040
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 ATPase family AAA domain-containing protein 5 Potency 14575.0 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 16353.5 nM None
Homo sapiens Cannabinoid CB1 receptor Inhibition 0.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Cannabinoid CB2 receptor Inhibition 11.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens C-C chemokine receptor type 8 Inhibition 8.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens C-X-C chemokine receptor type 4 Inhibition 10.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Cyclooxygenase-1 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 Inhibition -10.0 % 10.1021/acs.jmedchem.9b01924
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 Formyl peptide receptor 1 Inhibition 1.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Glucose-dependent insulinotropic receptor Inhibition 3.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Guanine nucleotide-binding protein G(s), subunit alpha Potency 31622.8 nM None
Homo sapiens HERG AC50 460.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor Inhibition 5.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Liver microsomes CL 66.0 mL.min-1.g-1 10.1016/j.bmcl.2011.12.005
Homo sapiens Monoamine oxidase A AC50 30000.0 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 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 M4 Inhibition -8.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Neuropeptide S receptor Inhibition -15.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Orexin receptor 2 Inhibition 9.0 % 10.1021/acs.jmedchem.9b01924
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 Prolactin-releasing peptide receptor Inhibition 3.0 % 10.1021/acs.jmedchem.9b01924
Homo sapiens Prostanoid IP receptor Inhibition -3.0 % 10.1021/acs.jmedchem.9b01924
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 organic anion transporter family member 1B1 Inhibition 72.87 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 88.88 % 10.1124/mol.112.084152
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 Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Mus musculus B16 Activity 50.0 % 10.1016/j.bmc.2010.04.086
Mus musculus B16 IC50 68900.0 nM 10.1016/j.bmc.2010.04.086
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.9b01924
Mus musculus Mus musculus IA nan None 10.1021/jm0108045
Mus musculus Mus musculus TIME 0.04083 hr 10.1021/jm0108045
Plasmodium falciparum Plasmodium falciparum Potency 11689.1 nM None
Plasmodium falciparum Plasmodium falciparum Potency 13115.4 nM None
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus INS1(832/13) Activity 28.7 % 10.1016/j.ejmech.2019.111976
Rattus norvegicus INS1(832/13) Activity 63.0 % 10.1016/j.ejmech.2019.111976
Rattus norvegicus INS1(832/13) Activity nan None 10.1016/j.ejmech.2019.111976
Rattus norvegicus INS1(832/13) EC50 11000.0 nM 10.1016/j.ejmech.2019.111976
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 index 0.1041 None 10.1101/2020.04.03.023846
None Unchecked Ac50 8.913 uM None
None Unchecked AC50 8912.5 nM None
None Unchecked Activity nan None 10.1016/j.ejmech.2019.111976

Metabolism Information