Navigation

name Structure Reference Source Properties Activities Metabolism

Tetrahydropalmatine

AlkaPlorer ID: AK001767

Synonym: None

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

Structure

SMILES: COC1=CC2=C(C=C1OC)[C@@H]1CC3=C(CN1CC2)C(OC)=C(OC)C=C3

copy

InChI: InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

copy

InChIKey: AEQDJSLRWYMAQI-KRWDZBQOSA-N

copy

Source

Species Genus Family Order Class Phylum Kingdom Domain
Fibraurea recisa Fibraurea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis chinensis Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stephania rotunda Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis decumbens Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phellodendron chinense Phellodendron Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Passiflora coccinea Passiflora Passifloraceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Achyrocline satureioides Achyrocline Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Maytenus octogona Maytenus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis yanhusuo Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Heliothis maritima Heliothis Noctuidae Lepidoptera Insecta Arthropoda Metazoa Eukaryota
Dovyalis hebecarpa Dovyalis Salicaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ixeris repens Ixeris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stephania pierrei Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis japonica Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis deltoidea Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eremophila oppositifolia Eremophila Scrophulariaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Taxillus yadoriki Taxillus Loranthaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Agathosma bisulca Agathosma Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coptis teeta Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis ternata Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Brickellia dentata Brickellia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tylopilus plumbeoviolaceus Tylopilus Boletaceae Boletales Agaricomycetes Basidiomycota Fungi Eukaryota
Russula paludosa Russula Russulaceae Russulales Agaricomycetes Basidiomycota Fungi Eukaryota
Stephania delavayi Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Karwinskia subcordata Karwinskia Rhamnaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis turtschaninovii Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium vulpinum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Phellodendron amurense Phellodendron Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Funneliformis mosseae Funneliformis Glomeraceae Glomerales Glomeromycetes Mucoromycota Fungi Eukaryota

Properties Information

Molecule Weight: 355.434

TPSA？: 40.16

MolLogP？: 3.376500000000002

Number of H-Donors: 0

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Alpha-1a adrenergic receptor Inhibition 41.2 % 10.1021/acs.jmedchem.6b01217
Homo sapiens Coagulation factor III IC50 22.78 nM 10.1016/j.bmc.2012.11.002
Homo sapiens Dopamine D1 receptor Activity -7.43 % 10.1016/j.bmc.2019.04.014
Homo sapiens Dopamine D1 receptor IC50 1630.0 nM 10.1016/j.bmc.2019.04.014
Homo sapiens Dopamine D1 receptor Inhibition 96.9 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D1 receptor Ki 153.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D1 receptor Ki 231.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Activity 3.51 % 10.1016/j.bmc.2019.04.014
Homo sapiens Dopamine D2 receptor IC50 450.0 nM 10.1016/j.bmc.2019.04.014
Homo sapiens Dopamine D2 receptor Inhibition 85.4 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Ki 1125.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D2 receptor Ki 5000.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D3 receptor Ki 1371.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D4 receptor Ki 1000.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D5 receptor Ki 305.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Estrogen receptor alpha Activity 95.0 % 10.1016/j.bmcl.2011.11.041
Homo sapiens Estrogen receptor alpha Activity 118.84 % 10.1016/j.bmcl.2011.11.041
Homo sapiens Histone deacetylase 6 Inhibition -31.7 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -6.46 % 10.6019/CHEMBL4808148
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 84.9 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 5000.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 33.0 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki nan None 10.1016/j.bmc.2012.12.016
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 186.7 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 106.92 % 10.1124/mol.112.084152
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase Inhibition 25.0 % 10.1016/j.ejmech.2011.01.016
Plasmodium falciparum Plasmodium falciparum ED50 5020.0 ng/ml 10.1021/np50099a005
Plasmodium falciparum Plasmodium falciparum ED50 10000.0 ng/ml 10.1021/np50099a005
Plasmodium falciparum Plasmodium falciparum IC50 32600.0 nM 10.1016/j.bmc.2009.02.050
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 7.96 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.0185 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -11.62 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.09 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/np990639k
None ADMET log Pe -4.7 None 10.1021/np300882f
None Unchecked Activity nan None 10.1021/acs.jnatprod.1c00429

Metabolism Information

AKRT ID Reaction Reaction Link ID
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
AKRT011690 COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2.C[SAH]>>COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3C[N+]1(C)CC2 RXN-23319
AKRT011691 COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2>>COc1cc2c(cc1OC)-c1cc3ccc(OC)c(OC)c3c[n+]1CC2 RXN-8699