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Isotetrandrine

AlkaPlorer ID: AK002056

Synonym: None

IUPAC Name: (1R,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaene

Structure

SMILES: COC1=CC=C2C=C1OC1=CC=C(C=C1)C[C@@H]1C3=C(C=C(OC)C(=C3)OC3=C4C(=CC(OC)=C3OC)CCN(C)[C@H]4C2)CCN1C

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InChI: InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30+/m1/s1

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InChIKey: WVTKBKWTSCPRNU-IHLOFXLRSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Lathyrus aphaca Lathyrus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alnus formosana Alnus Betulaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thalictrum minus Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium implicatum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Asparagus umbellatus Asparagus Asparagaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Choisya ternata Choisya Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis japonica Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Carapichea ipecacuanha Carapichea Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Erythrina chiriquensis Erythrina Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Physeter catodon Physeter Physeteridae Artiodactyla Mammalia Chordata Metazoa Eukaryota
Stephania cephalantha Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyota bartayresiana Dictyota Dictyotaceae Dictyotales Phaeophyceae None None Eukaryota
Dalbergia sissoides Dalbergia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thalictrum atriplex Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phelipanche arenaria Phelipanche Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pestalotiopsis disseminata Pestalotiopsis Sporocadaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Chondrodendron microphyllum Chondrodendron Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lampropeltis getula Lampropeltis Colubridae Squamata Lepidosauria Chordata Metazoa Eukaryota
Elettaria cardamomum Elettaria Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tapinoma erraticum Tapinoma Formicidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota
Thalictrum foliolosum Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cornus officinalis Cornus Cornaceae Cornales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bupleurum scorzonerifolium Bupleurum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Melianthus major Melianthus Francoaceae Geraniales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stephania tetrandra Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cyclea barbata Cyclea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anaxagorea luzonensis Anaxagorea Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Clitocybe fasciculata Clitocybe Clitocybaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Cyclea peltata Cyclea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Vulpicida juniperinus Vulpicida Parmeliaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Thalictrum foetidum Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phoradendron reichenbachianum Phoradendron Viscaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis thunbergii Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thalictrum petaloideum Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thalictrum simplex Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 622.7620000000001

TPSA？: 61.860000000000014

MolLogP？: 7.162400000000009

Number of H-Donors: 0

Number of H-Acceptors: 8

RingCount: 8

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Candida albicans Candida albicans MIC80 64.0 ug.mL-1 10.1021/acs.jmedchem.7b01413
Electrophorus electricus Acetylcholinesterase Inhibition -1.02 % 10.1016/j.bmc.2012.09.040
Entamoeba histolytica Entamoeba histolytica IC50 13.81 ug.mL-1 10.1007/s00044-011-9767-1
Equus caballus Cholinesterase Inhibition 21.91 % 10.1016/j.bmc.2012.09.040
Homo sapiens 786-0 GI50 24717.24 nM None
Homo sapiens A498 GI50 19678.86 nM None
Homo sapiens A549 GI50 18323.14 nM None
Homo sapiens ACHN GI50 13427.65 nM None
Homo sapiens BT-549 GI50 18238.96 nM None
Homo sapiens CAKI-1 GI50 15995.58 nM None
Homo sapiens CCRF-CEM GI50 16865.53 nM None
Homo sapiens COLO 205 GI50 11641.26 nM None
Homo sapiens DU-145 GI50 19678.86 nM None
Homo sapiens EKVX GI50 23067.47 nM None
Homo sapiens HCC 2998 GI50 12705.74 nM None
Homo sapiens HCT-116 GI50 17660.38 nM None
Homo sapiens HCT-15 GI50 11168.63 nM None
Homo sapiens HL-60 GI50 10789.47 nM None
Homo sapiens Homo sapiens AUC 192.0 ng/ml 10.1016/j.ejmech.2017.06.047
Homo sapiens Homo sapiens T1/2 120.0 hr 10.1016/j.ejmech.2017.06.047
Homo sapiens HOP-92 GI50 10000.0 nM None
Homo sapiens Hs-578T GI50 16710.91 nM None
Homo sapiens HT-29 GI50 6251.73 nM None
Homo sapiens IGROV-1 GI50 20653.8 nM None
Homo sapiens K562 GI50 4159.11 nM None
Homo sapiens KM12 GI50 17619.76 nM None
Homo sapiens LOX IMVI GI50 8790.23 nM None
Homo sapiens M14 GI50 11066.24 nM None
Homo sapiens Malme-3M GI50 20606.3 nM None
Homo sapiens MCF7 GI50 14028.14 nM None
Homo sapiens MDA-MB-231 GI50 14723.13 nM None
Homo sapiens MDA-MB-435 GI50 18793.17 nM None
Homo sapiens MDA-N GI50 13645.83 nM None
Homo sapiens NCI/ADR-RES GI50 21330.45 nM None
Homo sapiens NCI/ADR-RES TGI 58.0 % 10.1016/j.ejmech.2017.06.047
Homo sapiens NCI-H226 GI50 24945.95 nM None
Homo sapiens NCI-H23 GI50 15776.11 nM None
Homo sapiens NCI-H322M GI50 24660.39 nM None
Homo sapiens NCI-H460 GI50 15205.48 nM None
Homo sapiens NCI-H522 GI50 12589.25 nM None
Homo sapiens OVCAR-3 GI50 18155.16 nM None
Homo sapiens OVCAR-4 GI50 17947.34 nM None
Homo sapiens OVCAR-5 GI50 26121.61 nM None
Homo sapiens OVCAR-8 GI50 17947.34 nM None
Homo sapiens Panel NCI-60 (60 carcinoma cell lines) GI50 10.0 nM 10.1021/jm049838d
Homo sapiens PC-3 GI50 18879.91 nM None
Homo sapiens RXF 393 GI50 1442.12 nM None
Homo sapiens SF-268 GI50 21677.04 nM None
Homo sapiens SF-295 GI50 16330.52 nM None
Homo sapiens SF-539 GI50 8892.01 nM None
Homo sapiens SK-MEL-2 GI50 25822.6 nM None
Homo sapiens SK-MEL-28 GI50 21527.82 nM None
Homo sapiens SK-MEL-5 GI50 11830.42 nM None
Homo sapiens SK-OV-3 GI50 40179.08 nM None
Homo sapiens SN12C GI50 18323.14 nM None
Homo sapiens SNB-19 GI50 20417.38 nM None
Homo sapiens SNB-75 GI50 12387.97 nM None
Homo sapiens SR GI50 2409.91 nM None
Homo sapiens SW-620 GI50 36307.81 nM None
Homo sapiens T47D GI50 21183.61 nM None
Homo sapiens TK-10 GI50 19054.61 nM None
Homo sapiens U-251 GI50 22233.1 nM None
Homo sapiens U-937 Activity 69.0 % 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 FC 1.2 None 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 IC50 50000.0 nM 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 MED 12.0 uM 10.1016/j.bmc.2012.06.017
Homo sapiens UACC-257 GI50 11271.97 nM None
Homo sapiens UACC-62 GI50 21827.3 nM None
Homo sapiens UO-31 GI50 16218.1 nM None
Rattus norvegicus Dopamine transporter IC50 4200.0 nM 10.1021/np50124a001
Rattus norvegicus Rattus norvegicus AUC 6279.0 ng.hr.mL-1 10.1016/j.ejmech.2017.06.047
Rattus norvegicus Rattus norvegicus Cmax 380.56 nM 10.1016/j.ejmech.2017.06.047
Rattus norvegicus Rattus norvegicus T1/2 20.0 hr 10.1016/j.ejmech.2017.06.047
Rattus norvegicus Rattus norvegicus Tmax 6.0 hr 10.1016/j.ejmech.2017.06.047
None Unchecked FC 20.0 None 10.1016/j.ejmech.2017.06.047
None Unchecked Ratio IC50 0.15 None 10.1021/np50124a001
None Unchecked Ratio IC50 7.9 None 10.1021/np50124a001
None Unchecked TGI 62.0 % 10.1016/j.ejmech.2017.06.047
None Unchecked TGI 76.0 % 10.1016/j.ejmech.2017.06.047

Metabolism Information