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(S)-tetrahydrocolumbamine

AlkaPlorer ID: AK007694

Synonym: 'Isocorypalmine', '', 'O10-Methylstepholidine', '(-)-Isocorypalmine', '(S)-tetrahydrocolumbamine', '(13aS)-5,8,13,13a-tetrahydro-3,9,10-trimethoxy-6H-Dibenzoa,gquinolizin-2-ol', 'Tetrahydrocolumbamine', '(+)-Isocorypalmine', '(13aS)-5,8,13,13a-tetrahydro-3,9,10-trimethoxy-6H-dibenzoa,gquinolizin-2-ol', '5,8,13,13a-Tetrahydrocolumbamine', '(S)-Tetrahydrocolumbamine'

IUPAC Name: (13aS)-3,9,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-2-ol

Structure

SMILES: COC1=CC2=C(C=C1O)[C@@H]1CC3=C(CN1CC2)C(OC)=C(OC)C=C3

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InChI: InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

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InChIKey: KDFKJOFJHSVROC-INIZCTEOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Fibraurea recisa Fibraurea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ulex airensis Ulex Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stachys plumosa Stachys Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hydrastis canadensis Hydrastis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper methysticum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis yanhusuo Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artabotrys maingayi Artabotrys Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diospyros ebenum Diospyros Ebenaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Papaver somniferum Papaver Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Uncaria rhynchophylla Uncaria Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ligularia sagitta Ligularia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Angelica dahurica Angelica Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lappula echinata Lappula Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis ophiocarpa Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thuja plicata Thuja Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Corydalis ternata Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stereocaulon alpinum Stereocaulon Stereocaulaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Labidiaster annulatus Labidiaster Labidiasteridae Forcipulatida Asteroidea Echinodermata Metazoa Eukaryota
Senna spectabilis Senna Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chaetomorpha moniligera Chaetomorpha Cladophoraceae Cladophorales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
Lasius niger Lasius Formicidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota
Corydalis cava Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces aizunensis Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Symphytum officinale Symphytum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyostelium longosporum Dictyostelium Dictyosteliaceae Dictyosteliales Eumycetozoa Evosea None Eukaryota
Corydalis turtschaninovii Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Psacalium peltatum Psacalium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 341.40700000000004

TPSA？: 51.16000000000001

MolLogP？: 3.073500000000002

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Dopamine D1 receptor Inhibition 99.2 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D1 receptor Ki 4.5 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D1 receptor Ki 6.2 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D2 receptor Inhibition 90.9 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Ki 41.8 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D2 receptor Ki 91.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D3 receptor Ki 37.3 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D4 receptor Ki 77.4 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D5 receptor Ki 9.5 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 71.1 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki nan None 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 40.5 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki nan None 10.1016/j.bmc.2012.12.016

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011654 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[33S]>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 None
AKRT011656 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[SAH]>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 2.1.1.117-RXN
AKRT011663 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2.C[33S]>>COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 None
AKRT011664 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2.C[SAH]>>COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 2.1.1.89-RXN
AKRT011665 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2>>COc1cc2c(cc1O)-c1cc3ccc(OC)c(OC)c3c[n+]1CC2 RXN-8698
AKRT011666 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4 1.1.3.36-RXN