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yohimbine

AlkaPlorer ID: AK001223

Synonym: '', '17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester', 'Yohimbine', 'quebrachine', 'beta-Yohimbine', 'SMR000440723', 'Quebrachin', '17-Epialloyohimbine', 'Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16.alpha.,17.alpha.)-', '3-epi-alpha-yohimbine', 'yohimbic acid methyl ester', 'Rauhimbin\nRauhimbine\nCorynanthin\nCOYNANTHINE\nCorynanthine\nYohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.beta.,17.alpha.)-\nYohimban-16.beta.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester', 'MLSMR', '(+)-yohimbine', 'Yohimbine monohydrochloride', 'aphrodine', 'YOHIMBINE', '17-epi-Alloyohimbine', 'MLS000863574', '(3beta)-17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester', 'Yohimbine, hydrochloride', 'corynine', 'Yohimban-16.alpha.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester, monohydrochloride', 'Yohimbine hydrochloride', '.psi.-Yohimbine\nPSEUDOYOHIMBINE\nPseudoyohimbine\nYohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (3.beta.,16.alpha.,17.alpha.)-\n3.beta.-Yohimban-16.alpha.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester', '(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester', 'pseudoyohimbine', '(3R)-17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester', 'Johimbin', 'Yohimbin'

IUPAC Name: methyl (1S,15R,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

Structure

SMILES: COC(=O)[C@H]1[C@H]2C[C@H]3C4=C(CCN3C[C@@H]2CC[C@@H]1O)C1=CC=CC=C1N4

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InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19-/m0/s1

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InChIKey: BLGXFZZNTVWLAY-DKJBZYCGSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 354.45

TPSA？: 65.56

MolLogP？: 2.6471

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 15.76 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 6.02 % 10.1016/j.bmc.2012.09.040
Escherichia coli K-12 Beta-lactamase AmpC Potency 14125.4 nM None
Homo sapiens Adrenergic receptor alpha-2 IC50 211000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 IC50 340000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 IC50 871000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 IC50 1038000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 5600.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 25000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 37000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 170000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 330000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 640000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 1300000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 Kd 2500000.0 nM 10.1016/0960-894X(96)00406-4
Homo sapiens Adrenergic receptor alpha-2 pC30 5.0 None 10.1021/jm00370a011
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
Homo sapiens Alpha-1a adrenergic receptor Kd 251.19 nM 10.1021/jm00370a011
Homo sapiens Alpha-1a adrenergic receptor Ki 29.0 nM 10.1016/j.bmcl.2004.11.032
Homo sapiens Alpha-1a adrenergic receptor Ki 142.0 nM 10.1021/jm00019a001
Homo sapiens Alpha-1b adrenergic receptor Ki 517.0 nM 10.1021/jm00019a001
Homo sapiens Alpha-1d adrenergic receptor Ki 253.0 nM 10.1021/jm00019a001
Homo sapiens Alpha-2a adrenergic receptor Ki 1218.0 nM 10.1021/jm00019a001
Homo sapiens Alpha-2b adrenergic receptor Ki 455.0 nM 10.1021/jm00019a001
Homo sapiens Alpha-2c adrenergic receptor Ki 161.0 nM 10.1021/jm00019a001
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 50118.7 nM None
Homo sapiens Cytochrome P450 1A2 AC50 12589.25 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 501.19 nM None
Homo sapiens Cytochrome P450 2D6 AC50 39810.72 nM None
Homo sapiens Cytochrome P450 2D6 Ki 80.0 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Potency 501.2 nM None
Homo sapiens Cytochrome P450 2D6 Potency 39810.7 nM None
Homo sapiens Cytochrome P450 3A4 AC50 25118.86 nM None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 Potency 25118.9 nM None
Homo sapiens DNA polymerase iota Potency 17782.8 nM None
Homo sapiens Flap endonuclease 1 Potency 25118.9 nM None
Homo sapiens Geminin Potency 23109.3 nM None
Homo sapiens HeLa Activity nan None 10.1021/acs.jnatprod.8b00324
Homo sapiens HepG2 Activity nan None 10.1021/acs.jnatprod.8b00324
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 12589.3 nM None
Homo sapiens HT-29 Activity nan None 10.1021/acs.jnatprod.8b00324
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 15848.9 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 79432.8 nM None
Homo sapiens MCF7 Activity nan None 10.1021/acs.jnatprod.8b00324
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 28183.8 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 50118.7 nM None
Homo sapiens Prelamin-A/C Potency 35481.3 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 39810.7 nM None
Homo sapiens Sodium channel alpha subunits; brain (Types I, II, III) Inhibition 33.7 % 10.1021/jm00381a019
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 62.61 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 84.73 % 10.1124/mol.112.084152
Homo sapiens Sphingomyelin phosphodiesterase Potency 25118.9 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 7943.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 32642.7 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 35481.3 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Mus musculus B-cell line IC50 40500.0 nM 10.1021/acs.jnatprod.8b00324
Mus musculus Murine T-cell line IC50 27600.0 nM 10.1021/acs.jnatprod.8b00324
Plasmodium falciparum Plasmodium falciparum Potency 14715.7 nM None
Plasmodium falciparum Plasmodium falciparum Potency 20786.5 nM None
Rattus norvegicus Adrenergic receptor alpha Selectivity index 1.22 None 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha Selectivity index 1.9 None 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha-1 IC50 220.0 nM 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha-1 Kd 562.34 nM 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha-2 IC50 17500.0 nM 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha-2 Kd 9332.54 nM 10.1021/jm00370a011
Rattus norvegicus Adrenergic receptor alpha-2 Ki 15800.0 nM 10.1021/jm00354a001
Rattus norvegicus Inositol monophosphatase 1 Potency 1995.3 nM None
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 794.3 nM None
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 14125.4 nM None
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 31622.8 nM None
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit Ki 1250.0 nM 10.1021/jm00019a001
Schistosoma mansoni Thioredoxin glutathione reductase Potency 28183.8 nM None
None Unchecked pK 6.29 None 10.1021/jm0408969
None Unchecked pK 6.6 None 10.1021/jm0408969
None Unchecked pK 6.85 None 10.1021/jm0408969
None Unchecked Potency 31622.8 nM None
None Unchecked Selectivity index 1.6 None 10.1021/jm00370a011

Metabolism Information