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Fangchinoline

AlkaPlorer ID: AK005850

Synonym: None

IUPAC Name: (1S,14S)-9,20,25-trimethoxy-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-dodecaen-21-ol

Structure

SMILES: COC1=CC=C2C=C1OC1=CC=C(C=C1)C[C@H]1C3=C(C=C(OC)C(=C3)OC3=C4C(=CC(OC)=C3O)CCN(C)[C@H]4C2)CCN1C

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InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m0/s1

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InChIKey: IIQSJHUEZBTSAT-VMPREFPWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Lathyrus aphaca Lathyrus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cocculus trilobus Cocculus Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium implicatum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Asparagus umbellatus Asparagus Asparagaceae Asparagales 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 epigaea Stephania Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyota bartayresiana Dictyota Dictyotaceae Dictyotales Phaeophyceae None None Eukaryota
Pachygone dasycarpa Pachygone Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phelipanche arenaria Phelipanche Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chondrodendron microphyllum Chondrodendron Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Elettaria cardamomum Elettaria Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tapinoma erraticum Tapinoma Formicidae Hymenoptera Insecta Arthropoda Metazoa 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
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
Phoradendron reichenbachianum Phoradendron Viscaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sinomenium acutum Sinomenium Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 608.7350000000001

TPSA？: 72.86

MolLogP？: 6.859400000000009

Number of H-Donors: 1

Number of H-Acceptors: 8

RingCount: 8

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Entamoeba histolytica Entamoeba histolytica IC50 14.71 ug.mL-1 10.1007/s00044-011-9767-1
Homo sapiens A498 GI50 17988.71 nM None
Homo sapiens A549 GI50 31477.48 nM None
Homo sapiens A549 IC50 10000.0 nM 10.1021/np400084t
Homo sapiens Ataxin-2 Potency 19952.6 nM None
Homo sapiens Beta-2 adrenergic receptor Potency 11220.2 nM None
Homo sapiens Beta-2 adrenergic receptor Potency 11582.1 nM None
Homo sapiens CAKI-1 GI50 3539.97 nM None
Homo sapiens CCRF-CEM GI50 24266.1 nM None
Homo sapiens COLO 205 GI50 15776.11 nM None
Homo sapiens Cyclooxygenase-1 IC50 129000.0 nM 10.1021/np049655u
Homo sapiens DLD-1 GI50 23442.29 nM None
Homo sapiens DMS-114 GI50 24717.24 nM None
Homo sapiens DMS-273 GI50 14723.13 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3F Potency 31622.8 nM None
Homo sapiens EKVX GI50 4446.31 nM None
Homo sapiens Flap endonuclease 1 Potency 50118.7 nM None
Homo sapiens Geminin Potency 290.9 nM None
Homo sapiens Geminin Potency 20596.2 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 7079.5 nM None
Homo sapiens HCC 2998 GI50 17619.76 nM None
Homo sapiens HCT-116 GI50 13304.54 nM None
Homo sapiens HCT-15 GI50 13273.94 nM None
Homo sapiens HEK-293T CC50 1000.0 nM 10.1021/acs.jnatprod.3c00159
Homo sapiens HEL IC50 22710.0 nM 10.1016/j.ejmech.2019.111898
Homo sapiens HepG2 IC50 9080.0 nM 10.1016/j.bmcl.2016.12.029
Homo sapiens HepG2 Potency 7943.3 nM None
Homo sapiens HL-60 GI50 13995.87 nM None
Homo sapiens HL-60 IC50 10000.0 nM 10.1021/np400084t
Homo sapiens HOP-18 GI50 32210.69 nM None
Homo sapiens HOP-62 GI50 37583.74 nM None
Homo sapiens HOP-92 GI50 7638.36 nM None
Homo sapiens HT-29 GI50 22335.72 nM None
Homo sapiens IGROV-1 GI50 27101.92 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 16360.1 nM None
Homo sapiens K562 GI50 11402.5 nM None
Homo sapiens K562 IC50 5940.0 nM 10.1016/j.ejmech.2019.111898
Homo sapiens KB ED50 9210.0 nM 10.1021/np980144f
Homo sapiens KM12 GI50 16788.04 nM None
Homo sapiens KM-20L2 GI50 1702.16 nM None
Homo sapiens LOX IMVI GI50 5296.63 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 56234.1 nM None
Homo sapiens Lysosomal alpha-glucosidase Potency 12589.3 nM None
Homo sapiens M19-MEL GI50 22646.44 nM None
Homo sapiens Malme-3M GI50 30690.22 nM None
Homo sapiens MCF7 GI50 26607.25 nM None
Homo sapiens MCF7 IC50 5000.0 nM 10.1021/np400084t
Homo sapiens MCF7 IC50 10100.0 nM 10.1016/j.bmcl.2016.12.029
Homo sapiens MCF7 IC50 17410.0 nM 10.1016/j.ejmech.2019.111898
Homo sapiens MDA-MB-231 IC50 58610.0 nM 10.1016/j.ejmech.2019.111898
Homo sapiens microRNA 21 Potency 23280.9 nM None
Homo sapiens MOLT-4 GI50 11694.99 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 7943.3 nM None
Homo sapiens NCI/ADR-RES GI50 29376.5 nM None
Homo sapiens NCI-H226 GI50 39902.49 nM None
Homo sapiens NCI-H23 GI50 39994.47 nM None
Homo sapiens NCI-H322M GI50 36475.39 nM None
Homo sapiens NCI-H460 GI50 21777.1 nM None
Homo sapiens NCI-H522 GI50 27478.94 nM None
Homo sapiens OVCAR-3 GI50 21627.19 nM None
Homo sapiens OVCAR-4 GI50 26485.0 nM None
Homo sapiens OVCAR-5 GI50 46344.69 nM None
Homo sapiens OVCAR-8 GI50 5248.07 nM None
Homo sapiens P-glycoprotein 1 Activity 2.4 fold 10.1097/00001813-199803000-00008
Homo sapiens P-glycoprotein 1 Inhibition nan % 10.1016/j.bmc.2020.115553
Homo sapiens RPMI-8226 GI50 8912.51 nM None
Homo sapiens RXF 393 GI50 16519.62 nM None
Homo sapiens SF-268 GI50 30199.52 nM None
Homo sapiens SF-295 GI50 16904.41 nM None
Homo sapiens SF-539 GI50 20276.83 nM None
Homo sapiens SK-MEL-2 GI50 26546.06 nM None
Homo sapiens SK-MEL-28 GI50 21777.1 nM None
Homo sapiens SK-MEL-5 GI50 13645.83 nM None
Homo sapiens SK-OV-3 GI50 28444.61 nM None
Homo sapiens SMMC-7721 IC50 10000.0 nM 10.1021/np400084t
Homo sapiens SN12C GI50 38815.04 nM None
Homo sapiens SN12K1 GI50 18323.14 nM None
Homo sapiens SNB-19 GI50 43752.21 nM None
Homo sapiens SNB-75 GI50 28707.81 nM None
Homo sapiens SNB-78 GI50 40738.03 nM None
Homo sapiens SW480 IC50 10000.0 nM 10.1021/np400084t
Homo sapiens SW-620 GI50 15031.42 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 8199.5 nM None
Homo sapiens U-251 GI50 27164.39 nM None
Homo sapiens U-937 Activity 102.0 % 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 FC 2.0 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 25.0 uM 10.1016/j.bmc.2012.06.017
Homo sapiens UACC-257 GI50 9484.18 nM None
Homo sapiens UACC-62 GI50 20749.14 nM None
Homo sapiens UO-31 GI50 25527.01 nM None
Homo sapiens XF498 GI50 27352.69 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 12589.3 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 35481.3 nM None
Mus musculus P388 GI50 1995.26 nM None
Mus musculus P388/ADR GI50 2582.26 nM None
Plasmodium falciparum Plasmodium falciparum IC50 179.0 nM 10.1021/np980144f
Plasmodium falciparum Plasmodium falciparum IC50 306.0 nM 10.1021/np980144f
Plasmodium falciparum Plasmodium falciparum Potency 1852.6 nM None
Plasmodium falciparum Plasmodium falciparum Potency 2936.2 nM None
Rattus norvegicus INS1 AC50 5844.0 nM None
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Activity nan None 10.1021/acs.jnatprod.3c00159
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 193.0 nM 10.1021/acs.jnatprod.3c00159
Staphylococcus aureus Staphylococcus aureus MIC 6.0 ug.mL-1 10.1016/j.bmc.2019.07.023
Staphylococcus aureus Staphylococcus aureus MIC 256.0 ug.mL-1 10.1016/j.bmc.2019.07.023
None NON-PROTEIN TARGET IC50 10000.0 nM 10.1021/np400084t
None Unchecked Activity nan None 10.1021/acs.jnatprod.3c00159
None Unchecked IC50 20000.0 nM 10.1016/j.ejmech.2019.111898
None Unchecked Inhibition 82.4 % 10.1021/np50075a001
None Unchecked Potency 7079.5 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 12589.3 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 18356.4 nM None
None Unchecked Potency 20596.2 nM None
None Unchecked Selectivity Index 30.0 None 10.1021/np980144f
None Unchecked Selectivity Index 51.0 None 10.1021/np980144f

Metabolism Information