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Cephaeline

AlkaPlorer ID: AK004465

Synonym: None

IUPAC Name: (1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

Structure

SMILES: CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1C[C@H]1NCCC2=CC(O)=C(OC)C=C21

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InChI: InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1

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InChIKey: DTGZHCFJNDAHEN-OZEXIGSWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Mentha aquatica Mentha Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Osteospermum jucundum Osteospermum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alangium villosum Alangium Cornaceae Cornales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helichrysum heterolasium Helichrysum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Clonostachys rosea Clonostachys Bionectriaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Amauroascus aureus Amauroascus Onygenaceae Onygenales Eurotiomycetes Ascomycota Fungi Eukaryota
Cedrus deodara Cedrus Pinaceae Pinales Pinopsida Streptophyta Viridiplantae Eukaryota
Carapichea ipecacuanha Carapichea Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hirsutella nivea Hirsutella Ophiocordycipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Ascochyta caulina Ascochyta Didymellaceae Pleosporales Dothideomycetes Ascomycota Fungi Eukaryota
Tragopogon porrifolius Tragopogon Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coryphantha elephantidens Coryphantha Cactaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces avidinii Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Acodontaster conspicuus Acodontaster Odontasteridae Valvatida Asteroidea Echinodermata Metazoa Eukaryota
Alangium salviifolium Alangium Cornaceae Cornales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helichrysum revolutum Helichrysum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 466.6220000000003

TPSA？: 63.19000000000001

MolLogP？: 4.640400000000005

Number of H-Donors: 2

Number of H-Acceptors: 6

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero IC50 5.3 ug.mL-1 10.1021/np030086k
Entamoeba histolytica Entamoeba histolytica IC50 3.26 ug.mL-1 10.1007/s00044-011-9767-1
Homo sapiens A549 IC50 3000.0 nM 10.1021/acs.jnatprod.9b00670
Homo sapiens BT-549 IC50 0.86 ug.mL-1 10.1021/np030086k
Homo sapiens BXPC-3 Activity 0.024 ug ml-1 10.1021/np700738k
Homo sapiens DU-145 Activity 0.0098 ug ml-1 10.1021/np700738k
Homo sapiens HeLa IC50 7600.0 nM 10.1021/acs.jnatprod.9b00670
Homo sapiens HL-60 IC50 14.9 ug.mL-1 10.1021/np030086k
Homo sapiens KB IC50 0.33 ug.mL-1 10.1021/np030086k
Homo sapiens KM-20L2 Activity 0.022 ug ml-1 10.1021/np700738k
Homo sapiens Leukocyte adhesion glycoprotein LFA-1 alpha IC50 10.0 ug.mL-1 10.1021/np030086k
Homo sapiens Leukocyte adhesion glycoprotein LFA-1 alpha MIC 6.9 ug.mL-1 10.1021/np030086k
Homo sapiens NCI-H460 Activity 0.022 ug ml-1 10.1021/np700738k
Homo sapiens OVCAR-3 Activity 0.032 ug ml-1 10.1021/np700738k
Homo sapiens SF-295 Activity 0.018 ug ml-1 10.1021/np700738k
Homo sapiens SK-MEL IC50 0.25 ug.mL-1 10.1021/np030086k
Homo sapiens SK-OV-3 IC50 0.18 ug.mL-1 10.1021/np030086k
Homo sapiens SK-OV-3 IC50 100.0 nM 10.1021/acs.jnatprod.9b00670
Leishmania donovani Leishmania donovani IC50 0.03 ug.mL-1 10.1021/np030086k
Leishmania donovani Leishmania donovani IC90 1.5 ug.mL-1 10.1021/np030086k
Mus musculus P388 Activity 0.0027 ug ml-1 10.1021/np700738k
Plasmodium falciparum Plasmodium falciparum IC50 0.0277 ug.mL-1 10.1021/np030086k
Plasmodium falciparum Plasmodium falciparum IC50 0.038 ug.mL-1 10.1021/np030086k
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None Unchecked Ratio 2.17 None 10.1021/np030086k
None Unchecked Ratio IC50 132.0 None 10.1021/np030086k
None Unchecked Ratio IC50 193.0 None 10.1021/np030086k

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010234 CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(O)c(O)cc21.C[SAH]>>CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(O)c(OC)cc21 R11685
AKRT010235 CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(O)c(OC)cc21.C[SAH]>>CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(OC)c(OC)cc21 RXN-13796