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7alpha-Hydroxy-7H-mitragynine

AlkaPlorer ID: AK008242

Synonym: '7-Hydroxymitragynin', '7beta-hydroxy-7H-mitraciliatine'

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

Structure

SMILES: CC[C@@H]1CN2CC[C@@]3(O)C(=NC4=CC=CC(OC)=C43)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

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InChI: InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15+,18+,23+/m1/s1

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InChIKey: RYENLSMHLCNXJT-CYXFISRXSA-N

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Properties Information

Molecule Weight: 414.5020000000002

TPSA？: 80.59000000000002

MolLogP？: 2.792600000000001

Number of H-Donors: 1

Number of H-Acceptors: 7

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Cavia porcellus Inhibition 86.3 % 10.1021/jm010576e
Cavia porcellus Cavia porcellus Inhibition 99.0 % 10.1021/jm010576e
Cavia porcellus Cavia porcellus pD2 8.2 None 10.1021/jm010576e
Cavia porcellus Cavia porcellus Relative potency 1071.0 % 10.1021/jm010576e
Cavia porcellus Kappa opioid receptor EC50 53.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Emax 77.0 % 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Ki 123.0 nM 10.1021/jm400143z
Cavia porcellus Kappa opioid receptor Ki 123.03 nM 10.1021/jm010576e
Cavia porcellus Kappa opioid receptor Ki 195.0 nM 10.1021/jm400143z
Cavia porcellus Kappa opioid receptor Ki 1000.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Ratio Ki 10.0 None 10.1016/j.ejmech.2019.111701
Cavia porcellus Kappa opioid receptor Relative affinity 10.1 % 10.1021/jm010576e
Cavia porcellus Mu opioid receptor EC50 53.0 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Emax 77.0 % 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Ki 7.2 nM 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Ki 9.8 nM 10.1021/jm400143z
Cavia porcellus Mu opioid receptor Ki 13.0 nM 10.1021/jm400143z
Cavia porcellus Mu opioid receptor Ki 13.49 nM 10.1021/jm010576e
Cavia porcellus Mu opioid receptor Ratio Ki 10.0 None 10.1016/j.ejmech.2019.111701
Cavia porcellus Mu opioid receptor Relative affinity 83.3 % 10.1021/jm010576e
Cavia porcellus Opioid receptor (mu and kappa) Ratio Ki 10.0 None 10.1021/jm400143z
Homo sapiens Alpha-1a adrenergic receptor Inhibition 3.5 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1a adrenergic receptor Inhibition 10.1 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Inhibition -4.8 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1b adrenergic receptor Inhibition 5.9 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Inhibition -1.9 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-1d adrenergic receptor Inhibition 13.5 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2a adrenergic receptor Inhibition -6.7 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2a adrenergic receptor Inhibition -5.4 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2b adrenergic receptor Inhibition -9.9 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Alpha-2b adrenergic receptor Inhibition 1.1 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Inhibition 19.6 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Inhibition 93.7 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Kb 550.2 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Ki 154.88 nM 10.1021/jm010576e
Homo sapiens Delta opioid receptor Ki 236.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Delta opioid receptor Relative affinity 6.6 % 10.1021/jm010576e
Homo sapiens Kappa opioid receptor Inhibition 41.0 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Inhibition 97.8 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Kb 115.0 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Kappa opioid receptor Ki 74.1 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Activity nan None 10.1021/acs.jmedchem.6b00748
Homo sapiens Mu opioid receptor EC50 5.93 nM 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor EC50 7.6 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor EC50 34.5 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor EC50 239.88 nM 10.1021/acs.jmedchem.1c01273
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 95.55 % 10.1021/acs.jmedchem.1c01273
Homo sapiens Mu opioid receptor IC50 725.0 nM 10.1021/acs.jmedchem.6b00748
Homo sapiens Mu opioid receptor Inhibition 81.8 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Inhibition 100.7 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Mu opioid receptor Inhibition nan % 10.1021/acs.jmedchem.6b00748
Homo sapiens Mu opioid receptor Ki 7.16 nM 10.1021/acs.jmedchem.9b01465
Homo sapiens Nociceptin receptor Inhibition -1.6 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Nociceptin receptor Inhibition 3.4 % 10.1021/acs.jmedchem.9b01465
Homo sapiens Serotonin 1a (5-HT1a) receptor Activity 1.2 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 1a (5-HT1a) receptor Activity 3.1 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2a (5-HT2a) receptor Activity -0.2 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2a (5-HT2a) receptor Activity 3.9 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2b (5-HT2b) receptor Activity -1.4 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2b (5-HT2b) receptor Activity 12.4 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2c (5-HT2c) receptor Activity -18.3 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 2c (5-HT2c) receptor Activity -13.9 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 3a (5-HT3a) receptor Activity 8.2 % 10.1021/acs.jmedchem.1c00726
Homo sapiens Serotonin 3a (5-HT3a) receptor Activity 19.5 % 10.1021/acs.jmedchem.1c00726
Mus musculus Delta opioid receptor IC50 691.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Delta opioid receptor Ki 90.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Kappa opioid receptor IC50 2524.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Kappa opioid receptor Ki 131.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor EC50 53.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor Emax 77.0 % 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor Ki 37.0 nM 10.1021/acs.jmedchem.6b00748
Mus musculus Mu opioid receptor Ratio EC50 4.0 None 10.1021/acs.jmedchem.1c01111
Mus musculus Mu opioid receptor Ratio Ki 6.0 None 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus Activity nan None 10.1021/jm400143z
Mus musculus Mus musculus ED50 0.2 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 0.3 mg.kg-1 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus ED50 0.46 mg.kg-1 10.1021/acs.jmedchem.6b00748
Mus musculus Mus musculus Ratio ED50 3.0 None 10.1021/acs.jmedchem.1c01111
Mus musculus Mus musculus Ratio ED50 5.0 None 10.1021/acs.jmedchem.6b00748
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/acs.jmedchem.9b01465
Rattus norvegicus Rattus norvegicus ED50 1.91 mg.kg-1 10.1021/acs.jmedchem.9b01465
Rattus norvegicus Rattus norvegicus MPE 100.0 % 10.1021/acs.jmedchem.9b01465
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Activity -5.6 % 10.1021/acs.jmedchem.1c00726
Rattus norvegicus Serotonin 1b (5-HT1b) receptor Activity -0.8 % 10.1021/acs.jmedchem.1c00726
None ADMET Activity 11.6 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 17.4 ng.hr.mL-1 10.1021/acs.jnatprod.0c01163
None ADMET AUC 41.0 ng.hr.mL-1 10.1021/acs.jnatprod.0c01163
None ADMET CL 0.4 mL.min-1.kg-1 10.1021/acs.jmedchem.9b01465
None ADMET CL 3.7 mL.min-1.kg-1 10.1021/acs.jmedchem.9b01465
None ADMET Cmax 9.65 nM 10.1021/acs.jnatprod.0c01163
None ADMET Cmax 10.37 nM 10.1021/acs.jnatprod.0c01163
None ADMET Cp 270.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Ct 450.0 nM 10.1021/acs.jmedchem.1c01111
None ADMET Drug degradation -9.6 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation -6.8 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 1.6 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 6.0 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 6.4 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 6.6 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 9.1 % 10.1021/acs.jnatprod.0c01163
None ADMET Drug degradation 13.3 % 10.1021/acs.jnatprod.0c01163
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 0.02 None 10.1021/acs.jmedchem.9b01465
None ADMET Fu 0.1 None 10.1021/acs.jmedchem.9b01465
None ADMET Fu 0.852 None 10.1021/acs.jmedchem.9b01465
None ADMET Kel 0.0041 /min 10.1021/acs.jmedchem.9b01465
None ADMET PPB 90.0 % 10.1021/acs.jmedchem.9b01465
None ADMET T1/2 2.835 hr 10.1021/acs.jmedchem.9b01465
None ADMET Tmax 0.9 hr 10.1021/acs.jnatprod.0c01163
None ADMET Tmax 3.1 hr 10.1021/acs.jnatprod.0c01163
None Unchecked EC50 53.0 nM 10.1016/j.ejmech.2019.111701
None Unchecked Efficacy 99.0 % 10.1021/jm400143z
None Unchecked Emax 77.0 % 10.1016/j.ejmech.2019.111701
None Unchecked Inhibition 1071.0 % 10.1021/jm400143z
None Unchecked Ki 60.0 nM 10.1016/j.ejmech.2019.111701
None Unchecked Ki 145.0 nM 10.1021/jm400143z
None Unchecked Ki 155.0 nM 10.1021/jm400143z
None Unchecked Ratio Ki 10.0 None 10.1016/j.ejmech.2019.111701
None Unchecked Ratio Ki 10.0 None 10.1021/jm400143z

Metabolism Information