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name Structure Reference Source Properties Activities Metabolism

Mitragynine

AlkaPlorer ID: AK004938

Synonym: '', 'Speciogynine', 'Mitragynine', 'Speciogynin', 'Speciociliatine', 'Speciociliatin'

IUPAC Name: methyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Structure

SMILES: CC[C@@H]1CN2CCC3=C(NC4=C3C(OC)=CC=C4)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

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InChI: InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1

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InChIKey: LELBFTMXCIIKKX-QVRQZEMUSA-N

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Properties Information

Molecule Weight: 398.5030000000002

TPSA？: 63.790000000000006

MolLogP？: 3.8251000000000026

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Cavia porcellus Inhibition 83.1 % 10.1021/jm010576e
Cavia porcellus Cavia porcellus Inhibition 95.0 % 10.1021/jm010576e
Cavia porcellus Cavia porcellus pD2 6.59 None 10.1021/jm010576e
Cavia porcellus Cavia porcellus Relative potency 26.0 % 10.1021/jm010576e
Cavia porcellus Kappa opioid receptor EC50 230.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Emax 65.0 % 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Ki 123.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Ki 1000.0 nM 10.1021/jm400143z
Cavia porcellus Kappa opioid receptor Ki 1096.48 nM 10.1021/jm010576e
Cavia porcellus Kappa opioid receptor Relative affinity 0.6 % 10.1021/jm010576e
Cavia porcellus Mu opioid receptor EC50 230.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Emax 65.0 % 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Ki 7.2 nM 10.1021/jm400143z
Cavia porcellus Mu opioid receptor Ki 7.244 nM 10.1021/jm010576e
Cavia porcellus Mu opioid receptor Ki 13.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Relative affinity 88.7 % 10.1021/jm010576e
Cavia porcellus Opioid receptor (mu and kappa) Ratio Ki 1000.0 None 10.1021/jm400143z
Homo sapiens Alpha-1a adrenergic receptor Activity nan None 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1a adrenergic receptor Inhibition 13.2 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1a adrenergic receptor Inhibition 83.5 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1a adrenergic receptor Inhibition nan % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1a adrenergic receptor Ki 1340.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Inhibition -12.5 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Inhibition 40.3 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Inhibition nan % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Ki 4770.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Activity nan None 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Inhibition -2.1 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Inhibition 57.9 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Inhibition nan % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Ki 5480.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2a adrenergic receptor Inhibition -8.0 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2a adrenergic receptor Inhibition 40.4 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2a adrenergic receptor Ki 4720.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2b adrenergic receptor Inhibition -16.0 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2b adrenergic receptor Inhibition 25.1 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2b adrenergic receptor Ki 9290.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2c adrenergic receptor Inhibition nan % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2c adrenergic receptor Ki 2320.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Cytochrome P450 2D6 Ki 1100.0 nM 10.1021/acs.jnatprod.0c01163
Homo sapiens Cytochrome P450 3A T1/2 0.6233 hr 10.1021/acs.jmedchem.1c01111
Homo sapiens Delta opioid receptor IC50 10000.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Delta opioid receptor Inhibition 0.4 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Inhibition 18.3 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Ki 60.26 nM 10.1021/jm010576e
Homo sapiens Delta opioid receptor Ki 10000.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Delta opioid receptor Ki nan None 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Relative affinity 10.7 % 10.1021/jm010576e
Homo sapiens Kappa opioid receptor EC50 8500.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Kappa opioid receptor Inhibition 25.2 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Inhibition 88.3 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Ki 198.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Ki 772.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Mu opioid receptor Activity nan None 10.1021/acs.jmedchem.6b00748
Homo sapiens Mu opioid receptor EC50 0.4898 nM 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor EC50 241.2 nM 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor EC50 307.5 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor EC50 339.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Mu opioid receptor EC50 339.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor EC50 nan None 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor Emax 20.0 % 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor Emax 34.0 % 10.1021/acs.jmedchem.0c01915
Homo sapiens Mu opioid receptor Emax 84.68 % 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor Inhibition 29.0 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Inhibition 93.7 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Kb 179.2 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Ki 161.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Ki 161.0 nM 10.1021/acs.jnatprod.0c01055
Homo sapiens Mu opioid receptor Ki 233.0 nM 10.1021/acs.jmedchem.0c01915
Homo sapiens Nociceptin receptor Inhibition 4.3 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Nociceptin receptor Inhibition 40.8 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Serotonin 1a (5-HT1a) receptor Activity 9.7 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 1a (5-HT1a) receptor Activity 76.7 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 5880.0 nM 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2a (5-HT2a) receptor Activity -0.9 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2a (5-HT2a) receptor Activity 49.9 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 5010.0 nM 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2b (5-HT2b) receptor Activity 23.0 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2b (5-HT2b) receptor Activity 90.7 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2b (5-HT2b) receptor Ki 1260.0 nM 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2c (5-HT2c) receptor Activity -8.2 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2c (5-HT2c) receptor Activity 14.7 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 3a (5-HT3a) receptor Activity -12.7 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 3a (5-HT3a) receptor Activity -9.1 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 10000.0 nM 10.1021/acs.jmedchem.1c00726
Mus musculus Cytochrome P450 3A T1/2 0.4067 hr 10.1021/acs.jmedchem.1c01111
Mus musculus Cytochrome P450 3A T1/2 0.42 hr 10.1021/acs.jmedchem.1c01111
Mus musculus Cytochrome P450 3A T1/2 0.5967 hr 10.1021/acs.jmedchem.1c01111
Mus musculus Delta opioid receptor IC50 4000.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Delta opioid receptor Ki 1011.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Kappa opioid receptor IC50 4000.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Kappa opioid receptor Ki 231.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor EC50 203.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor Emax 65.0 % 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor Ki 230.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mus musculus Activity 100.0 % 10.1021/jm400143z
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 2.1 mg.kg-1 10.1021/acs.jmedchem.0c01915
Mus musculus Mus musculus ED50 4.0 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 6.25 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 25.95 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 57.3 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 106.0 mg.kg-1 10.1021/acs.jmedchem.0c01915
Mus musculus Mus musculus ED50 166.0 mg.kg-1 10.1021/acs.jmedchem.6b00748
Mus musculus Mus musculus TIME 0.25 hr 10.1021/acs.jmedchem.1c01111
Rattus norvegicus Rattus norvegicus Activity 25.0 % 10.1021/acs.jmedchem.1c00726
Rattus norvegicus Rattus norvegicus Activity 100.0 % 10.1021/acs.jmedchem.1c00726
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/acs.jmedchem.9b01465
Rattus norvegicus Rattus norvegicus ED50 26.8 mg.kg-1 10.1021/acs.jmedchem.1c00726
Rattus norvegicus Rattus norvegicus Emax 17.3 % 10.1021/acs.jmedchem.9b01465
Rattus norvegicus Rattus norvegicus Inhibition 18.0 % 10.1021/jm400143z
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Activity -0.2 % 10.1021/acs.jmedchem.1c00726
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Activity 8.2 % 10.1021/acs.jmedchem.1c00726
None ADMET Activity 34.7 cm 10.1021/acs.jmedchem.1c01111
None ADMET Activity nan None 10.1021/acs.jmedchem.1c01111
None ADMET Activity nan None 10.1021/acs.jmedchem.9b01465
None ADMET AUC 479.6 ng.hr.mL-1 10.1021/acs.jnatprod.0c01163
None ADMET AUC 849.8 ng.hr.mL-1 10.1021/acs.jmedchem.1c00726
None ADMET AUC 1306.8 ng.hr.mL-1 10.1021/acs.jnatprod.0c01163
None ADMET AUC/dose 83.7 hr.kg.ng/ml/mg 10.1021/acs.jnatprod.0c01163
None ADMET AUC/dose 136.1 hr.kg.ng/ml/mg 10.1021/acs.jnatprod.0c01163
None ADMET AUC/dose 213.1 hr.kg.ng/ml/mg 10.1021/acs.jnatprod.0c01163
None ADMET CL 1.9 mL.min-1.kg-1 10.1021/acs.jmedchem.9b01465
None ADMET CL 21.67 mL.min-1.kg-1 10.1021/acs.jmedchem.1c00726
None ADMET CL 31.2 mL.min-1.kg-1 10.1021/acs.jmedchem.9b01465
None ADMET Cmax 160.1 nM 10.1021/acs.jnatprod.0c01163
None ADMET Cmax 280.8 nM 10.1021/acs.jnatprod.0c01163
None ADMET Cmax/dose 11.1 kg.ng/ml/mg 10.1021/acs.jnatprod.0c01163
None ADMET Cmax/dose 11.7 kg.ng/ml/mg 10.1021/acs.jnatprod.0c01163
None ADMET Cmax/dose 46.5 ng/ml 10.1021/acs.jnatprod.0c01163
None ADMET Cp nan None 10.1021/acs.jmedchem.1c01111
None ADMET Ct 6.63 uM 10.1021/acs.jmedchem.1c01111
None ADMET Ct 9.74 uM 10.1021/acs.jmedchem.1c01111
None ADMET Ct 12.22 uM 10.1021/acs.jmedchem.1c01111
None ADMET Ct 30.06 uM 10.1021/acs.jmedchem.1c01111
None ADMET Ct nan None 10.1021/acs.jmedchem.1c01111
None ADMET Drug degradation -8.0 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation -0.8 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation -0.3 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 4.0 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 9.0 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 9.8 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 14.8 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug metabolism 0.028 uM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 0.035 uM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 0.037 uM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 0.094 uM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 3.1 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug metabolism 3.4 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug metabolism 12.6 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug metabolism 13.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 20.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 40.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 96.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 180.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 343.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 830.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism 1070.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug metabolism nan None 10.1021/acs.jmedchem.1c01111
None ADMET Drug recovery 80.0 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug recovery 90.0 % 10.1021/acs.jnatprod.0c01163
None ADMET ERH 0.09 None 10.1021/acs.jmedchem.9b01465
None ADMET Fu 0.02 None 10.1021/acs.jmedchem.9b01465
None ADMET Fu 0.307 None 10.1021/acs.jmedchem.9b01465
None ADMET Ke 0.12 L/hr 10.1021/acs.jmedchem.1c00726
None ADMET Kel 0.0347 /min 10.1021/acs.jmedchem.9b01465
None ADMET Ratio 1.6 None 10.1021/acs.jnatprod.0c01163
None ADMET T1/2 0.09833 hr 10.1021/acs.jmedchem.1c01111
None ADMET T1/2 0.125 hr 10.1021/acs.jmedchem.1c01111
None ADMET T1/2 0.225 hr 10.1021/acs.jmedchem.1c01111
None ADMET T1/2 0.3333 hr 10.1021/acs.jmedchem.9b01465
None ADMET Tmax 1.3 hr 10.1021/acs.jnatprod.0c01163
None ADMET Tmax 3.1 hr 10.1021/acs.jnatprod.0c01163
None ADMET Vd 8.0 L.kg-1 10.1021/acs.jmedchem.1c00726
None Unchecked EC50 230.0 nM 10.1016/j.ejmech.2019.111701
None Unchecked Efficacy 95.0 % 10.1021/jm400143z
None Unchecked Emax 65.0 % 10.1016/j.ejmech.2019.111701
None Unchecked Inhibition 26.0 % 10.1021/jm400143z
None Unchecked Ki 60.0 nM 10.1021/jm400143z
None Unchecked Ki 155.0 nM 10.1016/j.ejmech.2019.111701
None Unchecked Ratio Ki 10.0 None 10.1021/jm400143z

Metabolism Information