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(+)-N-Methyllaurotetanine

AlkaPlorer ID: AK002275

Synonym: 'N-Methyllaurotetanine', '2-O-Methylboldine', 'Lauroscholtzine'

IUPAC Name: (6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-ol

Structure

SMILES: COC1=CC2=C(C=C1O)C[C@H]1C3=C(C=C(OC)C(OC)=C23)CCN1C

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InChI: InChI=1S/C20H23NO4/c1-21-6-5-11-9-17(24-3)20(25-4)19-13-10-16(23-2)15(22)8-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1

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InChIKey: ZFLRVRLYWHNAEC-AWEZNQCLSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Phlomis crinita Phlomis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio congestus Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sarcophyton flexuosum Sarcophyton Alcyoniidae Malacalcyonacea Anthozoa Cnidaria Metazoa Eukaryota
Ormosia fordiana Ormosia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polanisia trachysperma Polanisia Cleomaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polygala senega Polygala Polygalaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eschscholzia californica Eschscholzia Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aspergillus microcysticus Aspergillus Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Melampodium leucanthum Melampodium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Boschniakia rossica Boschniakia Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Litsea cubeba Litsea Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rhododendron mucronulatum Rhododendron Ericaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lupinus cosentinii Lupinus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis yanhusuo Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis ternata Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Creosphaeria sassafras Creosphaeria Xylariaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Ramalina farinacea Ramalina Ramalinaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Bursera simaruba Bursera Burseraceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crotalaria stolzii Crotalaria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coffea liberica Coffea Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Juniperus scopulorum Juniperus Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Stellaria media Stellaria Caryophyllaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Renealmia alpinia Renealmia Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bursera kerberi Bursera Burseraceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cephalaria leucantha Cephalaria Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Delphinium denudatum Delphinium Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Annona squamosa Annona Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Nectandra Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Platycodon grandiflorus Platycodon Campanulaceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis turtschaninovii Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces nigrescens Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Emericellopsis minima Emericellopsis None Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Costasiella ocellifera Costasiella Costasiellidae None Gastropoda Mollusca Metazoa Eukaryota
Beesia calthifolia Beesia Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Annona cherimola Annona Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euonymus fortunei Euonymus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diplacus aurantiacus Diplacus Phrymaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Vachellia karroo Vachellia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Clerodendrum trichotomum Clerodendrum Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Curcuma aeruginosa Curcuma Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ericameria laricifolia Ericameria Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sideritis dasygnaphala Sideritis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Podocarpus elatus Podocarpus Podocarpaceae Araucariales Pinopsida Streptophyta Viridiplantae Eukaryota
Pellacalyx axillaris Pellacalyx Rhizophoraceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces parvisporogenes Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Euploca racemosa Euploca Heliotropiaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tephroseris kirilowii Tephroseris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Botrychium ternatum Botrychium Ophioglossaceae Ophioglossales Polypodiopsida Streptophyta Viridiplantae Eukaryota
Cissus quadrangularis Cissus Vitaceae Vitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Clinacanthus nutans Clinacanthus Acanthaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper brachystachyum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces melanogenes Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Morella pensylvanica Morella Myricaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alstonia angustiloba Alstonia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eucalyptus albens Eucalyptus Myrtaceae Myrtales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Micromonospora echinospora Micromonospora Micromonosporaceae Micromonosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 341.4070000000001

TPSA？: 51.16

MolLogP？: 3.170100000000001

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 Sigma-1 receptor Inhibition 50.0 % 10.1021/np500893h
Chlorocebus sabaeus Vero CC50 250000.0 nM 10.1021/np970382v
Chlorocebus sabaeus Vero MTC 125.0 uM 10.1021/np970382v
Electrophorus electricus Acetylcholinesterase IC50 nan None 10.1016/j.bmc.2016.07.043
Electrophorus electricus Acetylcholinesterase Inhibition 38.79 % 10.1016/j.bmc.2016.07.043
Equus caballus Cholinesterase IC50 218810.0 nM 10.1016/j.bmc.2016.07.043
Equus caballus Cholinesterase Inhibition 50.95 % 10.1016/j.bmc.2016.07.043
Homo sapiens Alpha-1a adrenergic receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Alpha-1b adrenergic receptor Ki 950.0 nM 10.1021/np500893h
Homo sapiens Alpha-1d adrenergic receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Alpha-2b adrenergic receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Alpha-2c adrenergic receptor Ki 950.0 nM 10.1021/np500893h
Homo sapiens Beta-2 adrenergic receptor Ki 950.0 nM 10.1021/np500893h
Homo sapiens Delta opioid receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Dopamine D1 receptor Ki 373.0 nM 10.1021/np500893h
Homo sapiens Dopamine D2 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Dopamine D3 receptor Ki 950.0 nM 10.1021/np500893h
Homo sapiens Dopamine D4 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Dopamine D5 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Dopamine transporter Ki 950.0 nM 10.1021/np500893h
Homo sapiens Histamine H1 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Histamine H3 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Histamine H4 receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Kappa opioid receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Mu opioid receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Muscarinic acetylcholine receptor M1 Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Muscarinic acetylcholine receptor M2 Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Muscarinic acetylcholine receptor M3 Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Muscarinic acetylcholine receptor M4 Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Muscarinic acetylcholine receptor M5 Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Neutrophil IC50 8360.0 nM 10.1016/j.bmcl.2020.127224
Homo sapiens Neutrophil Inhibition 50.0 % 10.1016/j.bmcl.2020.127224
Homo sapiens Norepinephrine transporter Ki 950.0 nM 10.1021/np500893h
Homo sapiens Serotonin 1a (5-HT1a) receptor EC50 160.0 nM 10.1021/np058114h
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 85.0 nM 10.1021/np058114h
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 314.0 nM 10.1021/np500893h
Homo sapiens Serotonin 1e (5-HT1e) receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki nan None 10.1021/np500893h
Homo sapiens Serotonin 2b (5-HT2b) receptor Ki 323.0 nM 10.1021/np500893h
Homo sapiens Serotonin 2c (5-HT2c) receptor Ki 950.0 nM 10.1021/np500893h
Homo sapiens Serotonin 3a (5-HT3a) receptor Inhibition 50.0 % 10.1021/np500893h
Homo sapiens Serotonin 5a (5-HT5a) receptor Ki 566.0 nM 10.1021/np500893h
Homo sapiens Serotonin 6 (5-HT6) receptor Ki 306.0 nM 10.1021/np500893h
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 20.0 nM 10.1021/np500893h
Homo sapiens Serotonin transporter Ki 950.0 nM 10.1021/np500893h
Plasmodium falciparum Plasmodium falciparum IC50 2.7 ug.mL-1 10.1021/np960195h
Plasmodium falciparum Plasmodium falciparum IC50 7.15 ug.mL-1 10.1021/np960195h
Poliovirus 2 Poliovirus 2 Activity 0.5 None 10.1021/np970382v
Poliovirus 2 Poliovirus 2 Activity 1.0 None 10.1021/np970382v
Poliovirus 2 Poliovirus 2 Activity 1.5 None 10.1021/np970382v
Poliovirus 2 Poliovirus 2 Activity 2.5 None 10.1021/np970382v
Poliovirus 2 Poliovirus 2 ED50 15.0 uM 10.1021/np970382v
Rattus norvegicus Peripheral-type benzodiazepine receptor Inhibition 50.0 % 10.1021/np500893h
None Sigma 2 receptor Inhibition 50.0 % 10.1021/np500893h
None Unchecked Inhibition 50.0 % 10.1021/np500893h
None Unchecked Ratio 16.7 None 10.1021/np970382v
None Unchecked Ratio Ki 16.0 None 10.1021/np500893h

Metabolism Information