Molecule

Piericidin A

AlkaPlorer ID: AK023796

Synonym: None

IUPAC Name: 2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one

Structure

SMILES: C/C=C(\C)[C@H](O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/CC1=C(C)C(O)=C(OC)C(OC)=N1

InChI: InChI=1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1

InChIKey: BBLGCDSLCDDALX-LKGBESRRSA-N

Reference

Efficacies of quorum sensing inhibitors, piericidin A and glucopiericidin A, produced by Streptomyces xanthocidicus KPP01532 for the control of potato soft rot caused by Erwinia carotovora subsp. atroseptica

PubChem CID: 6437838

CAS: 19855-42-6

LOTUS: LTS0052364

SuperNatural Ⅲ: SN0021048-06

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces mobaraensis	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 415.5740000000002

TPSA？: 71.81

MolLogP？: 5.457420000000006

Number of H-Donors: 2

Number of H-Acceptors: 5

RingCount: 1

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Mitochondrial complex I; NADH oxidoreductase	IC50	5.0	nM	10.1016/j.bmc.2007.11.023
Bos taurus	NADH-ubiquinone oxidoreductase chain 1	IC50	3.0	nM	10.1016/s0005-2728(02)00341-9
Bos taurus	NADH-ubiquinone oxidoreductase chain 1	IC50	6.026	nM	10.1016/0005-2728(95)00131-x
Homo sapiens	786-0	IC50	30000.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	0.28	g	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	0.9	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	1.1	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	1.3	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	7.4	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	15.9	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	75.6	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	81.9	%	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Activity	nan	None	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	IC50	400.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	IC50	1600.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	Ratio IC50	4.0	None	10.1021/acs.jmedchem.9b00598
Homo sapiens	ACHN	TGI	nan	None	10.1021/acs.jmedchem.9b00598
Homo sapiens	HeLa	Activity	nan	None	10.1021/acs.jnatprod.6b01059
Homo sapiens	HeLa	IC50	84900.0	nM	10.1021/acs.jnatprod.6b01059
Homo sapiens	HepG2	Activity	0.0	%	10.1021/acs.jmedchem.1c00175
Homo sapiens	HepG2	Activity	24.6	%	10.1021/acs.jmedchem.1c00175
Homo sapiens	HepG2	Activity	26.4	%	10.1021/acs.jmedchem.1c00175
Homo sapiens	HepG2	Activity	54.0	%	10.1021/acs.jmedchem.1c00175
Homo sapiens	HepG2	Activity	75.4	%	10.1021/acs.jmedchem.1c00175
Homo sapiens	HepG2	Activity	nan	None	10.1021/acs.jmedchem.1c00175
Homo sapiens	HK-2	IC50	100000.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	HL-60	IC50	82100.0	nM	10.1021/acs.jnatprod.6b01059
Homo sapiens	Indoleamine 2,3-dioxygenase	Inhibition	50.0	%	10.1021/acs.jnatprod.6b01059
Homo sapiens	LXR-alpha	Kd	3240.0	nM	10.1021/acs.jmedchem.1c00175
Homo sapiens	MDA-MB-231	IC50	100000.0	nM	10.1021/acs.jnatprod.6b01059
Homo sapiens	OS-RC-2	IC50	5200.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	Peroxiredoxin-1	Activity	nan	None	10.1021/acs.jmedchem.9b00598
Homo sapiens	Peroxiredoxin-1	Kd	2610.0	nM	10.1021/acs.jmedchem.9b00598
Homo sapiens	SW480	IC50	82100.0	nM	10.1021/acs.jnatprod.6b01059
Homo sapiens	U2OS	IC50	91500.0	nM	10.1021/acs.jnatprod.6b01059
Mus musculus	L929	IC50	0.43	nM	10.1016/j.bmc.2007.11.023
Mus musculus	Mus musculus	Activity	72.0	%	10.1021/acs.jmedchem.1c00175
Mus musculus	Mus musculus	Activity	nan	None	10.1021/acs.jmedchem.1c00175
Mus musculus	Mus musculus	Activity	nan	None	10.1021/acs.jmedchem.9b00598
Mus musculus	Mus musculus	FC	2.2	None	10.1021/acs.jmedchem.1c00175
Mus musculus	Mus musculus	FC	2.6	None	10.1021/acs.jmedchem.1c00175
Mus musculus	Mus musculus	FC	2.7	None	10.1021/acs.jmedchem.1c00175
Mus musculus	Mus musculus	FC	2.8	None	10.1021/acs.jmedchem.1c00175
None	ADMET	Activity	nan	None	10.1021/acs.jmedchem.1c00175
None	ADMET	Activity	nan	None	10.1021/acs.jmedchem.9b00598
None	ADMET	Cmax	36.94	nM	10.1021/acs.jmedchem.1c00175
None	ADMET	Drug uptake	443.45	ng/ml	10.1021/acs.jmedchem.1c00175
None	ADMET	FC	1.6	None	10.1021/acs.jmedchem.1c00175
None	ADMET	FC	2.3	None	10.1021/acs.jmedchem.1c00175
None	ADMET	FC	2.6	None	10.1021/acs.jmedchem.1c00175
None	ADMET	FC	3.7	None	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	2.8	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	10.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	14.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	26.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	27.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	30.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	34.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	50.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	55.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	56.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	58.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	60.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	66.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	72.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Activity	nan	None	10.1021/acs.jmedchem.1c00175
None	Unchecked	FC	1.3	None	10.1021/acs.jmedchem.1c00175
None	Unchecked	FC	2.7	None	10.1021/acs.jmedchem.1c00175
None	Unchecked	FC	3.1	None	10.1021/acs.jmedchem.1c00175
None	Unchecked	IC50	15.14	nM	10.1016/0005-2728(95)00131-x
None	Unchecked	IC50	234.42	nM	10.1016/0005-2728(95)00131-x
None	Unchecked	Imax	68.0	%	10.1016/j.bmc.2010.03.075
None	Unchecked	Imax	71.0	%	10.1016/j.bmc.2010.03.075
None	Unchecked	Imax	73.0	%	10.1016/j.bmc.2010.03.075
None	Unchecked	Imax	75.0	%	10.1016/j.bmc.2010.03.075
None	Unchecked	Imax	79.0	%	10.1016/j.bmc.2010.03.075
None	Unchecked	Inhibition	50.0	%	10.1016/0005-2728(95)00131-x
None	Unchecked	Inhibition	50.0	%	10.1021/acs.jnatprod.7b00694
None	Unchecked	Inhibition	65.0	%	10.1021/acs.jnatprod.6b00235
None	Unchecked	Inhibition	79.0	%	10.1021/acs.jmedchem.1c00175
None	Unchecked	Inhibition	nan	%	10.1016/0005-2728(95)00131-x