Molecule

Febrifugine

AlkaPlorer ID: AK026231

Synonym: None

IUPAC Name: 3-[3-[(2S,3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one

Structure

SMILES: O=C(C[C@@H]1NCCC[C@H]1O)CN1C=NC2=CC=CC=C2C1=O

InChI: InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m0/s1

InChIKey: FWVHWDSCPKXMDB-LSDHHAIUSA-N

Reference

Seasonal variation in the content of a febrifugine and isofebrifugine alkaloid mixture in aerial parts of Hydrangea macrophylla var. Otaksa, with special reference to its antimalarial activity

PubChem CID: 63224

CAS: 24159-07-7

LOTUS: LTS0038691

SuperNatural Ⅲ: SN0097661-04

NPASS: NPC113056

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Hydrangea chinensis	Hydrangea	Hydrangeaceae	Cornales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 301.34600000000006

TPSA？: 84.22

MolLogP？: 0.4685999999999995

Number of H-Donors: 2

Number of H-Acceptors: 6

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	NUGC	Activity	nan	None	10.1021/np010091t
Mus musculus	FM3A	EC50	170.0	nM	10.1021/jm010448q
Mus musculus	FM3A	EC50	170.0	nM	10.1021/jm0302086
Mus musculus	FM3A	EC50	170.0	nM	10.1021/jm990131e
Mus musculus	FM3A	Selectivity	243.0	None	10.1021/jm010448q
Mus musculus	L929	EC50	0.167	ug.mL-1	10.1021/jm0601809
Mus musculus	L929	Ratio EC50	118.0	None	10.1021/jm0601809
Mus musculus	Monoamine oxidase A	Activity	nan	None	10.1021/jm800656v
Mus musculus	Monoamine oxidase B	Activity	nan	None	10.1021/jm800656v
Mus musculus	Mus musculus	Activity	378000000.0	None	10.1021/np970433o
Mus musculus	Mus musculus	Activity	nan	None	10.1021/np970433o
Mus musculus	Mus musculus	ED50	1.0	umol.kg-1	10.1021/jm990131e
Mus musculus	Mus musculus	ED90	5.0	uM kg-1	10.1021/jm990131e
Mus musculus	Mus musculus	LD50	7.1	mg.kg-1	10.1021/jm0601809
Mus musculus	Mus musculus	MTD	35.0	mg kg-1	10.1016/j.bmc.2009.05.011
Plasmodium berghei	Plasmodium berghei	ED50	0.3	mg.kg-1	10.1021/jm0302086
Plasmodium berghei	Plasmodium berghei	ED50	0.41	mg.kg-1	10.1021/jm0601809
Plasmodium berghei	Plasmodium berghei	ED50	0.6	mg/kg/day	10.1016/j.bmc.2014.02.040
Plasmodium berghei	Plasmodium berghei	ED50	1.0	umol.kg-1	10.1021/jm010448q
Plasmodium berghei	Plasmodium berghei	ED50	2.3	mg.kg-1	10.1016/j.bmc.2009.05.011
Plasmodium berghei	Plasmodium berghei	ED50	2.3	mg.kg-1	10.1016/j.bmc.2011.11.053
Plasmodium berghei	Plasmodium berghei	ED90	1.5	mg kg-1	10.1021/jm0302086
Plasmodium berghei	Plasmodium berghei	ED90	5.0	uM kg-1	10.1021/jm010448q
Plasmodium berghei	Plasmodium berghei	MCD	12.0	mg kg-1	10.1016/j.bmc.2009.05.011
Plasmodium berghei	Plasmodium berghei	MCD	12.0	mg kg-1	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	EC50	0.0014	ug.mL-1	10.1021/jm0601809
Plasmodium falciparum	Plasmodium falciparum	EC50	0.00142	ug.mL-1	10.1021/jm0601809
Plasmodium falciparum	Plasmodium falciparum	EC50	0.076	nM	10.1016/j.bmc.2014.02.040
Plasmodium falciparum	Plasmodium falciparum	EC50	0.7	nM	10.1016/j.bmc.2014.02.040
Plasmodium falciparum	Plasmodium falciparum	EC50	0.7	nM	10.1021/jm0302086
Plasmodium falciparum	Plasmodium falciparum	EC50	0.7	nM	10.1021/jm990131e
Plasmodium falciparum	Plasmodium falciparum	EC50	1.2	nM	10.1021/jm990131e
Plasmodium falciparum	Plasmodium falciparum	EC50	200.0	nM	10.1016/j.bmc.2014.02.040
Plasmodium falciparum	Plasmodium falciparum	IC50	0.00076	ug.mL-1	10.1016/j.bmc.2009.05.011
Plasmodium falciparum	Plasmodium falciparum	IC50	1.6	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	1.6	nM	10.1016/j.bmcl.2006.01.009
Plasmodium falciparum	Plasmodium falciparum	IC50	1.9	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	1.9	nM	10.1016/j.bmcl.2006.01.009
Plasmodium falciparum	Plasmodium falciparum	IC50	2.0	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	2.1	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	3.1	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	4.2	nM	10.1016/j.bmc.2011.11.053
Plasmodium falciparum	Plasmodium falciparum	IC50	5.4	nM	10.1016/j.bmc.2011.11.053
Rattus norvegicus	Rattus norvegicus	MTD	35.0	mg kg-1	10.1016/j.bmc.2011.11.053
None	ADMET	Activity	10.0	%	10.1021/np970433o
None	ADMET	Activity	90.0	%	10.1021/np970433o
None	ADMET	Ratio LD50/ED50	17.0	None	10.1021/jm0601809
None	ADMET	TI	3.0	None	10.1016/j.bmc.2009.05.011
None	ADMET	TI	3.0	None	10.1016/j.bmc.2011.11.053
None	Hepatocyte	IC50	169.0	nM	10.1016/j.bmcl.2006.01.009
None	Macrophage	Activity	nan	None	10.1021/np970433o
None	Molecular identity unknown	Activity	91.0	%	10.1021/np970433o
None	Molecular identity unknown	Activity	nan	None	10.1021/np970433o
None	NON-PROTEIN TARGET	Activity	nan	None	10.1021/np010091t
None	NON-PROTEIN TARGET	Ratio	243.0	None	10.1021/jm0302086
None	NON-PROTEIN TARGET	Selectivity	142.0	None	10.1021/jm990131e
None	NON-PROTEIN TARGET	Selectivity	243.0	None	10.1021/jm990131e
None	Unchecked	EC50	700.0	nM	10.1021/jm010448q