Molecule

Sinomenine

AlkaPlorer ID: AK001978

Synonym: None

IUPAC Name: (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one

Structure

SMILES: COC1=C[C@@H]2[C@@H]3CC4=C(C(O)=C(OC)C=C4)[C@]2(CCN3C)CC1=O

InChI: InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1

InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N

Reference

Alkaloidal Constituents of the Tubers of Stephania cepharantha Cultivated in Japan: Structure of 3,4-Dehydrocycleanine, a New Bisbenzylisoquinoline Alkaloid.

PubChem CID: 5459308

CAS: 115-53-7

LOTUS: LTS0113046

SuperNatural Ⅲ: SN0150636-03

NPASS: NPC298339

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Brachylaena neriifolia	Brachylaena	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Stephania tetrandra	Stephania	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Sinomenium acutum	Sinomenium	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 329.39600000000013

TPSA？: 59.0

MolLogP？: 2.0181

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	Inhibition	4.63	%	10.1016/j.bmc.2012.09.040
Entamoeba histolytica	Entamoeba histolytica	IC50	18.49	ug.mL-1	10.1007/s00044-011-9767-1
Entamoeba histolytica	Entamoeba histolytica	IC50	56200.0	nM	10.1021/np000144r
Equus caballus	Cholinesterase	Inhibition	5.14	%	10.1016/j.bmc.2012.09.040
Homo sapiens	Cyclin-dependent kinase 2	IC50	50000.0	nM	10.1016/j.bmcl.2010.01.007
Homo sapiens	Histone deacetylase 6	Inhibition	-32.75	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	1.08	%	10.6019/CHEMBL4808148
Homo sapiens	KB	IC50	759000.0	nM	10.1021/np000144r
Homo sapiens	MCF7	Activity	nan	None	10.1016/j.bmc.2020.115986
Homo sapiens	MCF7	Inhibition	nan	%	10.1016/j.bmc.2020.115986
Homo sapiens	MDA-MB-231	Activity	nan	None	10.1016/j.bmc.2020.115986
Homo sapiens	MDA-MB-231	Inhibition	nan	%	10.1016/j.bmc.2020.115986
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	105.48	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	68.46	%	10.1124/mol.112.084152
Homo sapiens	TNF-alpha	Inhibition	nan	%	10.1016/j.ejmech.2012.12.051
Mus musculus	NIH3T3	IC50	100000.0	nM	10.1016/j.ejmech.2012.12.051
Mus musculus	Peritoneal macrophage	Inhibition	1.3	%	10.1016/j.ejmech.2021.113791
Mus musculus	Peritoneal macrophage	Inhibition	7.5	%	10.1016/j.ejmech.2021.113791
Mus musculus	RAW264.7	IC50	100000.0	nM	10.1016/j.bmc.2011.04.006
Mus musculus	RAW264.7	IC50	200000.0	nM	10.1016/j.ejmech.2012.01.036
Mus musculus	RAW264.7	Inhibition	-3.0	%	10.1016/j.bmc.2011.04.006
Mus musculus	RAW264.7	Inhibition	0.1	%	10.1016/j.bmc.2011.04.006
Mus musculus	RAW264.7	Inhibition	12.8	%	10.1016/j.bmc.2011.04.006
Mus musculus	RAW264.7	Inhibition	nan	%	10.1016/j.bmc.2011.04.006
Mus musculus	RAW264.7	Inhibition	nan	%	10.1016/j.ejmech.2012.01.036
Plasmodium falciparum	Plasmodium falciparum	IC50	152000.0	nM	10.1021/np000144r
Rattus norvegicus	Rattus norvegicus	Activity	nan	None	10.1016/j.ejmech.2020.112722
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	-0.1311	%	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	-7.02	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.13	%	10.6019/CHEMBL4495565
None	ADMET	LD50	1.1	g/Kg	10.1016/j.ejmech.2021.113791
None	Unchecked	Activity	nan	None	10.1016/j.bmc.2020.115986
None	Unchecked	Inhibition	2.8	%	10.1016/j.ejmech.2021.113791
None	Unchecked	Inhibition	nan	%	10.1016/j.bmc.2020.115986
None	Unchecked	Ka	0.68	10^3/M	10.1016/j.bmcl.2006.12.069
None	Unchecked	Ratio	4.41	None	10.1016/j.bmcl.2012.07.087