Molecule

Cinchonine

AlkaPlorer ID: AK002036

Synonym: None

IUPAC Name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol

Structure

SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)C1=CC=NC2=CC=CC=C12

InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1

InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N

Reference

Inhibitory Effects of Plant Secondary Metabolites on Cytotoxic Activity of Polymorphonuclear Leucocytes

PubChem CID: 90454

LOTUS: LTS0125043

SuperNatural Ⅲ: SN0189705-12

NPASS: NPC150048

{

NPAtlas: NPA001936

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Cinchona calisaya	Cinchona	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Diaporthe sp.	Diaporthe	Diaporthaceae	Diaporthales	Sordariomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 294.398

TPSA？: 36.36

MolLogP？: 3.164600000000002

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	Inhibition	5.94	%	10.1016/j.bmc.2012.09.040
Equus caballus	Cholinesterase	Inhibition	9.07	%	10.1016/j.bmc.2012.09.040
Homo sapiens	786-0	GI50	100000.0	nM	None
Homo sapiens	A498	GI50	62950.62	nM	None
Homo sapiens	A549	GI50	100000.0	nM	None
Homo sapiens	ACHN	GI50	100000.0	nM	None
Homo sapiens	BT-549	GI50	100000.0	nM	None
Homo sapiens	CAKI-1	GI50	100000.0	nM	None
Homo sapiens	COLO 205	GI50	100000.0	nM	None
Homo sapiens	Cytochrome P450 2D6	IC50	1800.0	nM	10.1021/jm049934e
Homo sapiens	Cytochrome P450 2D6	Ki	21000.0	nM	10.1021/jm049934e
Homo sapiens	DU-145	GI50	100000.0	nM	None
Homo sapiens	EKVX	GI50	73282.45	nM	None
Homo sapiens	Geminin	Potency	130.0	nM	None
Homo sapiens	Glucose transporter	Inhibition	-1.24	%	10.6019/CHEMBL3433997
Homo sapiens	HCT-116	GI50	100000.0	nM	None
Homo sapiens	HCT-15	GI50	100000.0	nM	None
Homo sapiens	HeLa	EC50	697.0	ug.mL-1	10.1016/j.bmcl.2012.06.062
Homo sapiens	HepG2	Inhibition	0.0	%	10.1038/nature09107
Homo sapiens	Histone deacetylase 6	Inhibition	-3.53	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	6.91	%	10.6019/CHEMBL4808148
Homo sapiens	HL-60	GI50	100000.0	nM	None
Homo sapiens	HOP-62	GI50	89949.76	nM	None
Homo sapiens	Hs-578T	GI50	1258.93	nM	None
Homo sapiens	HT-29	GI50	46773.51	nM	None
Homo sapiens	Huh-7	CC50	6250.0	nM	10.1073/pnas.0802982105
Homo sapiens	IGROV-1	GI50	19588.45	nM	None
Homo sapiens	K562	GI50	55207.74	nM	None
Homo sapiens	KM12	GI50	100000.0	nM	None
Homo sapiens	LOX IMVI	GI50	5395.11	nM	None
Homo sapiens	M14	GI50	38106.58	nM	None
Homo sapiens	Malme-3M	GI50	100000.0	nM	None
Homo sapiens	MCF7	GI50	100000.0	nM	None
Homo sapiens	MDA-MB-231	GI50	100000.0	nM	None
Homo sapiens	MDA-MB-435	GI50	100000.0	nM	None
Homo sapiens	MDA-N	GI50	100000.0	nM	None
Homo sapiens	MOLT-4	GI50	100000.0	nM	None
Homo sapiens	NCI/ADR-RES	GI50	100000.0	nM	None
Homo sapiens	NCI-H226	GI50	100000.0	nM	None
Homo sapiens	NCI-H23	GI50	100000.0	nM	None
Homo sapiens	NCI-H322M	GI50	100000.0	nM	None
Homo sapiens	NCI-H460	GI50	100000.0	nM	None
Homo sapiens	NCI-H522	GI50	100000.0	nM	None
Homo sapiens	Nuclear factor erythroid 2-related factor 2	Potency	32642.7	nM	None
Homo sapiens	OVCAR-3	GI50	100000.0	nM	None
Homo sapiens	OVCAR-4	GI50	58613.82	nM	None
Homo sapiens	OVCAR-5	GI50	100000.0	nM	None
Homo sapiens	OVCAR-8	GI50	100000.0	nM	None
Homo sapiens	PC-3	GI50	100000.0	nM	None
Homo sapiens	RPMI-8226	GI50	22908.68	nM	None
Homo sapiens	RXF 393	GI50	100000.0	nM	None
Homo sapiens	SF-268	GI50	100000.0	nM	None
Homo sapiens	SF-295	GI50	100000.0	nM	None
Homo sapiens	SF-539	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-2	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-28	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-5	GI50	100000.0	nM	None
Homo sapiens	SK-OV-3	GI50	100000.0	nM	None
Homo sapiens	SN12C	GI50	100000.0	nM	None
Homo sapiens	SNB-19	GI50	100000.0	nM	None
Homo sapiens	SNB-75	GI50	22803.42	nM	None
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	122.27	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	105.27	%	10.1124/mol.112.084152
Homo sapiens	SW-620	GI50	100000.0	nM	None
Homo sapiens	T47D	GI50	100000.0	nM	None
Homo sapiens	TK-10	GI50	100000.0	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	12995.3	nM	None
Homo sapiens	U-251	GI50	100000.0	nM	None
Homo sapiens	UACC-257	GI50	100000.0	nM	None
Homo sapiens	UACC-62	GI50	100000.0	nM	None
Homo sapiens	UO-31	GI50	52722.99	nM	None
Homo sapiens	WI-38	IC50	20.0	ug.mL-1	10.1016/j.ejmech.2013.06.004
Human immunodeficiency virus 1	Human immunodeficiency virus type 1 reverse transcriptase	IC50	200.0	ug.mL-1	10.1021/np50073a012
Leishmania mexicana	Glucose transporter	Inhibition	0.13	%	10.6019/CHEMBL3433997
Leishmania mexicana mexicana	Leishmania mexicana mexicana	IC50	20.0	ug.mL-1	10.1016/j.ejmech.2013.06.004
Plasmodium falciparum	Hexose transporter 1	Inhibition	1.12	%	10.6019/CHEMBL3433997
Plasmodium falciparum	Plasmodium falciparum	EC50	95.3	nM	10.1073/pnas.0802982105
Plasmodium falciparum	Plasmodium falciparum	EC50	110.0	nM	10.1073/pnas.0802982105
Plasmodium falciparum	Plasmodium falciparum	IC50	0.09	ug.mL-1	10.1016/j.ejmech.2013.06.004
Plasmodium falciparum	Plasmodium falciparum	IC50	5.0	nM	10.1128/aac.00431-10
Plasmodium falciparum	Plasmodium falciparum	IC50	21.0	nM	10.1007/s00044-007-9025-8
Plasmodium falciparum	Plasmodium falciparum	IC50	22.0	nM	10.1016/j.bmc.2012.03.042
Plasmodium falciparum	Plasmodium falciparum	IC50	51.0	nM	10.1016/s0960-894x(02)00173-7
Plasmodium falciparum	Plasmodium falciparum	IC50	56.0	nM	10.1007/s00044-007-9025-8
Plasmodium falciparum	Plasmodium falciparum	IC50	82.0	nM	10.1016/j.bmc.2012.03.042
Plasmodium falciparum	Plasmodium falciparum	IC50	220.0	nM	10.1016/s0960-894x(02)00173-7
Plasmodium falciparum	Plasmodium falciparum	IC50	292.5	nM	10.1016/j.ejmech.2015.05.044
Plasmodium falciparum	Plasmodium falciparum	IC50	23000.0	nM	10.1016/j.bmc.2010.01.068
Plasmodium falciparum	Plasmodium falciparum	Inhibition	2.0	%	10.1038/nature09107
Plasmodium falciparum	Plasmodium falciparum	Inhibition	3.0	%	10.1038/nature09107
Plasmodium falciparum	Plasmodium falciparum	Inhibition	100.0	%	10.1038/nature09107
Plasmodium falciparum	Plasmodium falciparum	Potency	4.1	nM	None
Plasmodium falciparum	Plasmodium falciparum	Potency	32.9	nM	None
Plasmodium falciparum	Plasmodium falciparum	XC50	766.16	nM	10.1038/nature09107
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	18.79	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-20.44	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.15	%	10.6019/CHEMBL4495565
Trichomonas vaginalis	Trichomonas vaginalis	MIC	nan	None	10.1016/j.bmcl.2012.06.062
Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	20.0	ug.mL-1	10.1016/j.ejmech.2013.06.004
Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	68030.0	nM	10.1016/j.ejmech.2015.05.044
None	ADMET	EC50	428.0	ug.mL-1	10.1016/j.bmcl.2012.06.062
None	ADMET	IC50	68030.0	nM	10.1016/j.ejmech.2015.05.044
None	Heme	IC50	23000.0	nM	10.1007/s00044-007-9025-8
None	Spermatozoa	Activity	0.5	%	10.1016/j.bmcl.2012.06.062
None	Unchecked	IC50	170000.0	nM	10.1016/j.bmc.2012.03.042
None	Unchecked	IC50	370000.0	nM	10.1016/j.bmc.2012.03.042
None	Unchecked	IC50	370000.0	nM	10.1016/j.bmcl.2004.05.031
None	Unchecked	IFI	0.73	%	10.1038/nature09107
None	Unchecked	IFI	4.688	%	10.1073/pnas.0802982105
None	Unchecked	Potency	199.5	nM	None
None	Unchecked	Potency	251.2	nM	None
None	Unchecked	Potency	920.0	nM	None
None	Unchecked	Ratio IC50	222.0	None	10.1016/j.ejmech.2013.06.004
None	Unchecked	Ratio IC50	222.0	None	10.1016/j.ejmech.2015.05.044
None	Unchecked	Ratio IC50	nan	None	10.1016/j.ejmech.2013.06.004
None	Unchecked	Ratio IC50	nan	None	10.1016/j.ejmech.2015.05.044