Molecule

Huperzine A

AlkaPlorer ID: AK014806

Synonym: '', '(-)-Huperzine A', 'Selagine', 'Huperzine A', 'Kimpukan A'

IUPAC Name: (1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

Structure

SMILES: C/C=C1\[C@H]2C=C(C)C[C@]1(N)C1=C(C2)NC(=O)C=C1

InChI: InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1

InChIKey: ZRJBHWIHUMBLCN-YQEJDHNASA-N

Reference

Malycorins A-C, New Lycopodium Alkaloids from Lycopodium phlegmaria

PubChem CID: 854026

LOTUS: LTS0153224

NPASS: NPC47298

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Huperzia serrata	Huperzia	Lycopodiaceae	Lycopodiales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Phlegmariurus squarrosus	Phlegmariurus	Lycopodiaceae	Lycopodiales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Alternaria sp.	Alternaria	Pleosporaceae	Pleosporales	Dothideomycetes	Ascomycota	Fungi	Eukaryota
Citrullus colocynthis	Citrullus	Cucurbitaceae	Cucurbitales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Huperzia selago	Huperzia	Lycopodiaceae	Lycopodiales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Berberis vulgaris	Berberis	Berberidaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 242.322

TPSA？: 58.88

MolLogP？: 1.9975

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Acetylcholinesterase	IC50	100.0	nM	10.1021/acs.jnatprod.9b00815
Canis lupus familiaris	Cholinesterase	IC50	10000000.0	nM	10.1016/j.bmcl.2020.126985
Electrophorus electricus	Acetylcholinesterase	IC50	5170.0	nM	10.1016/j.bmcl.2020.126985
Electrophorus electricus	Acetylcholinesterase	IC50	11000.0	nM	10.1021/acs.jnatprod.1c00600
Equus caballus	Cholinesterase	Inhibition	nan	%	10.1021/acs.jnatprod.1c00600
Homo sapiens	Acetylcholinesterase	IC50	33.0	nM	10.1021/acs.jnatprod.8b00592
Homo sapiens	Acetylcholinesterase	IC50	400.0	nM	10.1021/acs.jnatprod.8b00461
Homo sapiens	Acetylcholinesterase	IC50	600.0	nM	10.1021/acs.jnatprod.5b00600
Homo sapiens	Acetylcholinesterase	IC50	4300.0	nM	10.1021/acs.jnatprod.8b00705
Homo sapiens	Acetylcholinesterase	IC50	5280.0	nM	10.1016/j.bmcl.2022.128873
Homo sapiens	Acetylcholinesterase	K	0.003082	/s	10.1021/acs.jmedchem.0c01863
Homo sapiens	Acetylcholinesterase	K	1.81	/M/s	10.1021/acs.jmedchem.0c01863
Homo sapiens	Acetylcholinesterase	Kd	17.0	nM	10.1021/acs.jmedchem.0c01863
Homo sapiens	Acetyl-CoA acetyltransferase, mitochondrial	Inhibition	nan	%	10.1016/j.bmcl.2016.04.019
Homo sapiens	Butyrylcholinesterase	IC50	100000.0	nM	10.1021/acs.jnatprod.8b00592
Homo sapiens	Butyrylcholinesterase	IC50	10000000.0	nM	10.1016/j.bmcl.2022.128873
Homo sapiens	Glycogen synthase kinase-3 beta	Inhibition	nan	%	10.1021/acs.jnatprod.8b00592
Homo sapiens	Histone deacetylase 6	Inhibition	3.38	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	12.28	%	10.6019/CHEMBL4808148
Homo sapiens	Serotonin 1a (5-HT1a) receptor	EC50	nan	None	10.1016/j.bmc.2018.04.037
Rattus norvegicus	Acetylcholinesterase	IC50	82.0	nM	10.1016/j.bmc.2020.115820
Rattus norvegicus	Acetylcholinesterase	IC50	82.0	nM	10.1021/acs.jmedchem.6b00636
Rattus norvegicus	Acetylcholinesterase	IC50	98.0	nM	10.1016/j.ejmech.2017.08.025
Rattus norvegicus	Acetylcholinesterase	IC50	120.0	nM	10.1016/j.bmc.2018.04.037
Rattus norvegicus	Butyrylcholinesterase	IC50	36400.0	nM	10.1016/j.bmc.2018.04.037
Rattus norvegicus	Butyrylcholinesterase	IC50	36400.0	nM	10.1016/j.ejmech.2017.08.025
Rattus norvegicus	Butyrylcholinesterase	IC50	74430.0	nM	10.1016/j.bmc.2020.115820
Rattus norvegicus	Rattus norvegicus	Ratio	2.0	None	10.1016/j.bmc.2020.115820
Rattus norvegicus	Rattus norvegicus	Ratio	15.0	None	10.1016/j.bmc.2020.115820
Rattus norvegicus	Rattus norvegicus	Ratio	140.0	None	10.1016/j.bmc.2020.115820
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	0.2718	%	10.6019/CHEMBL4495564
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
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-5.72	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.1	%	10.6019/CHEMBL4495565
None	ADMET	LD50	2.0	mg.kg-1	10.1016/j.bmc.2020.115820
None	ADMET	LD50	4.0	mg.kg-1	10.1016/j.bmc.2020.115820
None	NON-PROTEIN TARGET	Activity	nan	None	10.1021/acs.jmedchem.6b00636
None	No relevant target	Activity	nan	None	10.1021/acs.jmedchem.6b00636
None	No relevant target	permeability	nan	None	10.1021/acs.jnatprod.8b00592
None	Unchecked	Ac50	11.22	uM	None
None	Unchecked	Ac50	44.67	uM	None
None	Unchecked	AC50	11220.2	nM	None
None	Unchecked	AC50	44668.4	nM	None
None	Unchecked	Activity	30.0	%	10.1016/j.bmc.2020.115820
None	Unchecked	Activity	85.0	%	10.1016/j.bmc.2020.115820
None	Unchecked	Activity	505.0	nM	10.1016/j.bmc.2020.115820
None	Unchecked	Activity	668.0	nM	10.1016/j.bmc.2020.115820
None	Unchecked	IC50	36400.0	nM	10.1021/acs.jmedchem.6b00636
None	Unchecked	Inhibition	16.0	%	10.1016/j.bmc.2020.115820
None	Unchecked	Inhibition	21.0	%	10.1016/j.bmc.2020.115820
None	Unchecked	Ki	5600.0	nM	10.1016/j.bmc.2020.115820
None	Unchecked	Ki	9500.0	nM	10.1016/j.bmc.2020.115820
None	Unchecked	Ratio IC50	15.1	None	10.1021/acs.jnatprod.8b00592
None	Unchecked	Ratio IC50	371.0	None	10.1016/j.ejmech.2017.08.025
None	Unchecked	Ratio IC50	444.0	None	10.1021/acs.jmedchem.6b00636