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Haemanthamine

AlkaPlorer ID: AK001685

Synonym: '', '(+)-Haemanthamine', '(3alpha,5alpha,11R,13beta,19alpha)-1, 2-Didehydro-3-methoxycrinan-11-ol', 'Crinamine', '(3beta,5alpha,11R,13beta,19alpha)-1,2-Didehydro-3-methoxycrinan-11-ol', 'Haemanthamine'

IUPAC Name: (1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

Structure

SMILES: CO[C@@H]1C=C[C@@]23C4=CC5=C(C=C4CN(C[C@@H]2O)[C@H]3C1)OCO5

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InChI: InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1

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InChIKey: YGPRSGKVLATIHT-HSHDSVGOSA-N

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Reference

Alkaloids from<i>Narcissus primigenius</i>

PubChem CID: 441593

CAS: 466-75-1

LOTUS: LTS0187515

SuperNatural Ⅲ: SN0449878-14

NPASS: NPC266176

data_source: manually

Properties Information

Molecule Weight: 301.34200000000004

TPSA？: 51.16000000000001

MolLogP？: 1.1866999999999996

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Entamoeba histolytica Entamoeba histolytica IC50 0.75 ug.mL-1 10.1016/j.bmcl.2019.126642
Homo sapiens 786-0 GI50 20090.93 nM None
Homo sapiens A2780 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens A549 GI50 23988.33 nM None
Homo sapiens A549 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens A549 IC50 2500.0 nM 10.1021/np3005425
Homo sapiens A549 IC50 3000.0 nM 10.1021/acs.jnatprod.9b00670
Homo sapiens A549 Ratio IC50 10.0 None 10.1021/np3005425
Homo sapiens Acetylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.9b00561
Homo sapiens Acetylcholinesterase IC50 452000.0 nM 10.1021/np0702077
Homo sapiens Acetylcholinesterase Inhibition 6.0 % 10.1021/acs.jnatprod.9b00561
Homo sapiens ACHN GI50 5128.61 nM None
Homo sapiens AGS IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens BT-549 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens Butyrylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.9b00561
Homo sapiens Butyrylcholinesterase Inhibition 13.0 % 10.1021/acs.jnatprod.9b00561
Homo sapiens CAKI-1 GI50 6223.0 nM None
Homo sapiens CCRF-CEM GI50 8336.81 nM None
Homo sapiens COLO 201 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens DLD-1 GI50 15275.66 nM None
Homo sapiens DMS-114 GI50 79615.94 nM None
Homo sapiens EKVX GI50 38018.94 nM None
Homo sapiens HCC 2998 GI50 15595.53 nM None
Homo sapiens HCT-15 GI50 17418.07 nM None
Homo sapiens HeLa IC50 1300.0 nM 10.1021/acs.jnatprod.9b00670
Homo sapiens HeLa S3 Inhibition nan % 10.1016/j.ejmech.2016.05.004
Homo sapiens HepG2 IC50 4800.0 nM 10.1021/np3005425
Homo sapiens HepG2 Ratio IC50 10.0 None 10.1021/np3005425
Homo sapiens HL-60 GI50 13963.68 nM None
Homo sapiens HL-60 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens HL-60 IC50 1400.0 nM 10.1021/np3005425
Homo sapiens HOP-18 GI50 21827.3 nM None
Homo sapiens HOP-92 GI50 14256.08 nM None
Homo sapiens HT-29 GI50 10423.17 nM None
Homo sapiens HT-29 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens HT-29 IC50 2100.0 nM 10.1021/np3005425
Homo sapiens HT-29 Ratio IC50 10.0 None 10.1021/np3005425
Homo sapiens IGROV-1 GI50 23120.65 nM None
Homo sapiens Jurkat IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens K562 GI50 7673.61 nM None
Homo sapiens K562 IC50 2500.0 nM 10.1021/np3005425
Homo sapiens K562 Ratio IC50 10.0 None 10.1021/np3005425
Homo sapiens KM12 GI50 13520.73 nM None
Homo sapiens KM-20L2 GI50 11694.99 nM None
Homo sapiens LOX IMVI GI50 6382.63 nM None
Homo sapiens LXFL 529 GI50 13614.45 nM None
Homo sapiens M14 GI50 5942.92 nM None
Homo sapiens M19-MEL GI50 16557.7 nM None
Homo sapiens Malme-3M GI50 14621.77 nM None
Homo sapiens MCF7 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens MDA-MB-231 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens MOLT-4 GI50 6471.43 nM None
Homo sapiens MOLT-4 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens NCI-H1299 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens NCI-H226 GI50 25409.73 nM None
Homo sapiens NCI-H23 GI50 23550.49 nM None
Homo sapiens NCI-H322M GI50 18238.96 nM None
Homo sapiens NCI-H460 GI50 15739.83 nM None
Homo sapiens NCI-H522 GI50 12050.36 nM None
Homo sapiens NHDF IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens OVCAR-3 GI50 46558.61 nM None
Homo sapiens OVCAR-4 GI50 3854.78 nM None
Homo sapiens OVCAR-5 GI50 41879.36 nM None
Homo sapiens OVCAR-8 GI50 27925.44 nM None
Homo sapiens PANC-1 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens RPMI-8226 GI50 29580.12 nM None
Homo sapiens RXF 393 GI50 18749.95 nM None
Homo sapiens SAOS-2 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens SF-268 GI50 29716.66 nM None
Homo sapiens SF-295 GI50 19054.61 nM None
Homo sapiens SF-539 GI50 28575.91 nM None
Homo sapiens SK-BR-3 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens SK-MEL-2 GI50 9162.2 nM None
Homo sapiens SK-MEL-28 GI50 18923.44 nM None
Homo sapiens SK-MEL-5 GI50 10000.0 nM None
Homo sapiens SK-OV-3 GI50 19453.6 nM None
Homo sapiens SK-OV-3 IC50 3700.0 nM 10.1021/acs.jnatprod.9b00670
Homo sapiens SN12C GI50 16143.59 nM None
Homo sapiens SNB-19 GI50 33342.64 nM None
Homo sapiens SNB-75 GI50 9057.33 nM None
Homo sapiens SNB-78 GI50 52480.75 nM None
Homo sapiens SR GI50 14996.85 nM None
Homo sapiens SW480 IC50 300.0 nM 10.1016/j.ejmech.2021.113839
Homo sapiens SW-620 GI50 15488.17 nM None
Homo sapiens TK-10 GI50 30831.88 nM None
Homo sapiens U-251 GI50 14996.85 nM None
Homo sapiens UACC-257 GI50 22646.44 nM None
Homo sapiens UACC-62 GI50 12882.5 nM None
Homo sapiens UO-31 GI50 16519.62 nM None
Homo sapiens XF498 GI50 16672.47 nM None
Leishmania donovani Leishmania donovani IC50 1.95 ug.mL-1 10.1016/j.bmcl.2019.126642
Plasmodium falciparum Plasmodium falciparum IC50 0.7 ug.mL-1 10.1016/j.bmc.2009.02.050
Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 0.49 ug.mL-1 10.1016/j.bmcl.2019.126642
Trypanosoma cruzi Trypanosoma cruzi IC50 1.8 ug.mL-1 10.1016/j.bmcl.2019.126642
None ADMET IC50 5000.0 nM 10.1021/np3005425
None No relevant target Peff nan None 10.1021/acs.jnatprod.9b00561
None Unchecked Inhibition 80.0 % 10.1016/j.bmcl.2018.01.041
None Unchecked Inhibition nan % 10.1016/j.bmcl.2018.01.041
None Unchecked Ratio IC50 10.0 None 10.1021/np3005425

Metabolism Information