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Cryptopleurine

AlkaPlorer ID: AK026624

Synonym: None

IUPAC Name: (14aR)-2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine

Structure

SMILES: COC1=CC=C2C3=C(C[C@H]4CCCCN4C3)C3=CC(OC)=C(OC)C=C3C2=C1

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InChI: InChI=1S/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1

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InChIKey: RSHYSOGXGSUUIJ-OAHLLOKOSA-N

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Properties Information

Molecule Weight: 377.4840000000001

TPSA？: 30.930000000000003

MolLogP？: 4.9294000000000056

Number of H-Donors: 0

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Entamoeba histolytica Entamoeba histolytica IC50 0.031 ug.mL-1 10.1007/s00044-011-9767-1
Hepacivirus hominis Hepatitis C virus EC50 0.6 nM 10.1016/j.bmc.2017.12.027
Hepatitis B virus Hepatitis B virus EC10 30.0 nM 10.1016/j.bmc.2017.12.027
Homo sapiens A-375 IC50 1.2 nM 10.1016/j.bmcl.2014.11.086
Homo sapiens A-375 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens A-431 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens A498 GI50 5.0 nM None
Homo sapiens A549 Activity nan None 10.1021/jm3001218
Homo sapiens A549 GI50 1.0 nM 10.1016/j.ejmech.2012.02.048
Homo sapiens A549 GI50 1.38 nM 10.1021/jm200330s
Homo sapiens A549 GI50 5.0 nM None
Homo sapiens A549 IC50 0.94 nM 10.1021/acs.jmedchem.5b00764
Homo sapiens A549 IC50 1.38 nM 10.1021/jm3001218
Homo sapiens A549 IC50 1.9 nM 10.1016/j.bmcl.2014.11.086
Homo sapiens A549 IC50 1.9 nM 10.1021/jm3001218
Homo sapiens A549 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens AGS Activity nan None 10.1021/np060081y
Homo sapiens Aryl hydrocarbon receptor nuclear translocator Activity nan None 10.1021/np060081y
Homo sapiens BT-20 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens BUD-8 IC50 6.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens CAKI-1 Activity 1.1 % 10.1021/acs.jmedchem.5b00764
Homo sapiens CAKI-1 Activity 8.1 % 10.1021/acs.jmedchem.5b00764
Homo sapiens CAKI-1 Activity 24.3 % 10.1021/acs.jmedchem.5b00764
Homo sapiens CAKI-1 Activity 66.5 % 10.1021/acs.jmedchem.5b00764
Homo sapiens CAKI-1 GI50 5.0 nM None
Homo sapiens CAKI-1 IC50 0.86 nM 10.1021/acs.jmedchem.5b00764
Homo sapiens CCRF-CEM GI50 5.0 nM None
Homo sapiens COLO 205 GI50 5.0 nM None
Homo sapiens Daudi IC50 2.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens DLD-1 GI50 5.0 nM None
Homo sapiens DMS-114 GI50 5.0 nM None
Homo sapiens DMS-273 GI50 5.0 nM None
Homo sapiens DU-145 GI50 1.59 nM 10.1021/jm200330s
Homo sapiens DU-145 IC50 1.59 nM 10.1021/jm3001218
Homo sapiens EKVX GI50 5.0 nM None
Homo sapiens HCC 2998 GI50 5.0 nM None
Homo sapiens HCT-116 GI50 5.0 nM None
Homo sapiens HCT-116 IC50 1.04 nM 10.1021/acs.jmedchem.5b00764
Homo sapiens HCT-15 GI50 18.62 nM None
Homo sapiens HCT-15 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens HCT-8 GI50 1.09 nM 10.1021/jm200330s
Homo sapiens HCT-8 IC50 1.91 nM 10.1021/jm3001218
Homo sapiens Heat shock cognate 71 kDa protein Activity nan None 10.1016/j.bmc.2017.12.027
Homo sapiens HEK293 IC50 nan None 10.1016/j.bmcl.2005.09.032
Homo sapiens HepG2 IC50 nan None 10.1016/j.bmcl.2005.09.032
Homo sapiens HepG2 2.2.15 Activity nan None 10.1016/j.bmc.2017.12.027
Homo sapiens HepG2 2.2.15 IC50 6.3 nM 10.1016/j.bmc.2017.12.027
Homo sapiens HL-60 GI50 1.0 nM 10.1016/j.ejmech.2012.02.048
Homo sapiens HL-60 GI50 5.0 nM None
Homo sapiens HOP-18 GI50 5.0 nM None
Homo sapiens HOP-62 GI50 5.0 nM None
Homo sapiens HOP-92 GI50 5.0 nM None
Homo sapiens HT-1376 IC50 4.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens HT-29 GI50 5.0 nM None
Homo sapiens HUVEC GI50 11.0 nM 10.1021/jm200330s
Homo sapiens Hypoxia-inducible factor 1 alpha Activity nan None 10.1021/np060081y
Homo sapiens Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Activity nan None 10.1021/np060081y
Homo sapiens Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha IC50 8.7 nM 10.1021/np060081y
Homo sapiens IGROV-1 GI50 5.0 nM None
Homo sapiens K562 GI50 5.0 nM None
Homo sapiens KB GI50 1.51 nM 10.1021/jm200330s
Homo sapiens KB IC50 1.51 nM 10.1021/jm3001218
Homo sapiens KHOS/NP IC50 10.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens KM12 GI50 5.0 nM None
Homo sapiens KM-20L2 GI50 5.0 nM None
Homo sapiens LOX IMVI GI50 5.0 nM None
Homo sapiens M19-MEL GI50 5.0 nM None
Homo sapiens Malme-3M GI50 5.0 nM None
Homo sapiens MCF7 GI50 5.0 nM None
Homo sapiens MCF7 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens MDA-MB-231 IC50 0.89 nM 10.1021/acs.jmedchem.5b00764
Homo sapiens MES-SA IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens MES-SA/Dx5 IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens MOLT-4 GI50 5.0 nM None
Homo sapiens MRC5 IC50 14.0 nM 10.1021/jm3001218
Homo sapiens NCI/ADR-RES GI50 5.0 nM None
Homo sapiens NCI-H226 GI50 5.0 nM None
Homo sapiens NCI-H23 GI50 1.637 nM None
Homo sapiens NCI-H322M GI50 5.0 nM None
Homo sapiens NCI-H460 GI50 5.0 nM None
Homo sapiens NCI-H522 GI50 1.718 nM None
Homo sapiens OVCAR-3 GI50 5.0 nM None
Homo sapiens OVCAR-4 GI50 5.0 nM None
Homo sapiens OVCAR-5 GI50 23.23 nM None
Homo sapiens OVCAR-8 GI50 5.0 nM None
Homo sapiens PA-1 IC50 2.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens PC-3 IC50 2.55 nM 10.1021/acs.jmedchem.5b00764
Homo sapiens PC-9 IC50 5.5 nM 10.1021/jm3001218
Homo sapiens Ramos IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
Homo sapiens RPMI-8226 GI50 5.0 nM None
Homo sapiens RXF 393 GI50 1.472 nM None
Homo sapiens SF-268 GI50 1.671 nM None
Homo sapiens SF-295 GI50 5.0 nM None
Homo sapiens SF-539 GI50 5.0 nM None
Homo sapiens SK-MEL-2 GI50 5.0 nM None
Homo sapiens SK-MEL-28 GI50 1.69 nM None
Homo sapiens SK-MEL-5 GI50 5.0 nM None
Homo sapiens SK-OV-3 GI50 5.0 nM None
Homo sapiens SN12C GI50 50.0 nM None
Homo sapiens SN12K1 GI50 5.0 nM None
Homo sapiens SNB-19 GI50 5.0 nM None
Homo sapiens SNB-75 GI50 1.607 nM None
Homo sapiens SNB-78 GI50 5.0 nM None
Homo sapiens SW-620 GI50 7.345 nM None
Homo sapiens TF-1 IC50 nan None 10.1016/j.bmcl.2005.09.032
Homo sapiens U-251 GI50 5.0 nM None
Homo sapiens UACC-257 GI50 16.14 nM None
Homo sapiens UACC-62 GI50 5.0 nM None
Homo sapiens UO-31 GI50 5.0 nM None
Homo sapiens XF498 GI50 23.23 nM None
Mus musculus CTLL IC50 nan None 10.1016/j.bmcl.2005.09.032
Mus musculus Mus musculus AUC 52.7 ng.hr.mL-1 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus AUC 53.2 ng.hr.mL-1 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus beta t1/2 nan None 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus CL 316.67 mL.min-1.kg-1 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus Cmax 200.81 nM 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus F 9.9 % 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus T1/2 0.9 hr 10.1021/acs.jmedchem.5b00764
Mus musculus Mus musculus Vdss 16.3 L.kg-1 10.1021/acs.jmedchem.5b00764
Mus musculus P388 GI50 5.0 nM None
Mus musculus P388/ADR GI50 5.0 nM None
Rattus norvegicus MAT-Ly-Lu IC50 3.0 nM 10.1016/j.bmcl.2005.09.032
None ADMET Ratio IC50/EC50 3.33 None 10.1016/j.bmc.2017.12.027
None NON-PROTEIN TARGET IC50 0.7 nM 10.1016/j.bmcl.2014.11.086
None NON-PROTEIN TARGET IC50 0.83 nM 10.1021/acs.jmedchem.5b00764
None NON-PROTEIN TARGET IC50 1.26 nM 10.1021/acs.jmedchem.5b00764
None NON-PROTEIN TARGET IC50 1.8 nM 10.1021/jm3001218
None NON-PROTEIN TARGET IC50 2.6 nM 10.1016/j.bmcl.2014.11.086
None NON-PROTEIN TARGET IC50 5.0 nM 10.1021/jm3001218
None NON-PROTEIN TARGET IC50 6.8 nM 10.1021/jm3001218
None No relevant target Solubility 1.0 ug.mL-1 10.1021/acs.jmedchem.5b00764
None No relevant target Solubility 160.0 ug.mL-1 10.1021/acs.jmedchem.5b00764
None Unchecked Activity nan None 10.1016/j.bmc.2017.12.027
None Unchecked IC50 2.0 nM 10.1016/j.bmc.2017.12.027

Metabolism Information