piericidin a profile

piericidin A: pyridine-substituted fatty alcohol antibiotic; minor descriptor (75-85); on-line & Index Medicus search ANTIBIOTICS (75-85); RN given refers to (S-(R*,R*-(all-E)))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

piericidin A : A member of the class of monohydroxypyridines that acts as an irreversible mitochondrial Complex I inhibitor that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of NADH:ubiquinone oxidoreductase [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	6437838
CHEMBL ID	272733
CHEBI ID	138511
SCHEMBL ID	18941698
SCHEMBL ID	19717606
MeSH ID	M0263022

Synonym
NCGC00180489-01
MEGXM0_000313
ACON1_001455
ACON0_001227
2,6,9,11-tridecatetraen-4-ol, 13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-, (all-e)-(4r,5r)-
piericidin
piericidine a
shaoguanmycin b
4-pyridinol, 2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-, (r-(r,r-(all-e)))-
sn 198e
piericidin a1
piericidin a
brn 1555726
4-pyridinol, 2-((2e,5e,7e,9r,10r,11e)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-
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
CHEBI:138511
2-[(2e,5e,7e,11e)-10r-hydroxy-3,7,9r,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4-pyridinol
(+)-piericidin a1
2738-64-9
ar 054
2-[(2e,5e,7e,9r,10r,11e)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol
BRD-K73581776-001-01-6
CHEMBL272733 ,
unii-8vt513uj9r
8vt513uj9r ,
bdbm50411905
4-pyridinol, 2-((2e,5e,7e,9r,10r,11e)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl)-5,6-dimethoxy-3-methyl-
piericidin a, (+)-
sn-198e
piericidin a from streptomyces mobaraensis, >=90.0% (hplc), liquid, green-yellow
SCHEMBL18941698
J-016753
SCHEMBL19717606
DTXSID80880044
19855-42-6
HY-114936
Q7191888
CS-0064672
hqh ,
piericidina
2-((2e,5e,7e,9r,10r,11e)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl)-5,6-dimethoxy-3-methylpyridin-4-ol

Excerpt	Reference	Relevance
"Piericidin A is a prototypical member of the group of the piericidins, a class of biologically active natural complex I inhibitors, isolated from streptomyces spp."	( Piericidin A aggravates Tau pathology in P301S transgenic mice. Carlsson, T; De Andrade, A; Deck, R; Gad El Hak, SA; Goedert, M; Höglinger, GU; Höllerhage, M; Oertel, WH; Respondek, G; Rösler, TW; Salama, M; Xu, H; Yamada, ES, 2014)	2.57

Role	Description
mitochondrial respiratory-chain inhibitor	null
EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor	A respiratory-chain inhibitor that interferes with the action of the the enzyme NADH:ubiquinone reductase (H(+)-translocating), EC 1.6.5.3.
antimicrobial agent	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
bacterial metabolite	Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
monohydroxypyridine	A hydroxypyridine carrying a single hydroxy substituent.
methylpyridines	Any member of the class of pyridines that carries at least one methyl substituent.
aromatic ether	Any ether in which the oxygen is attached to at least one aryl substituent.
secondary allylic alcohol	An allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to one other carbon and one hydrogen.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
succinate to cytochrome bo oxidase electron transfer	8	31
NADH to cytochrome bd oxidase electron transfer II	4	18
NADH to cytochrome bo oxidase electron transfer II	5	26
D-lactate to cytochrome bo oxidase electron transfer	5	27
glycerol-3-phosphate to cytochrome bo oxidase electron transfer	5	29
proline to cytochrome bo oxidase electron transfer	5	31
succinate to cytochrome bd oxidase electron transfer	7	23
NADH to cytochrome bo oxidase electron transfer I	17	34
NADH to cytochrome bd oxidase electron transfer I	16	27
pyruvate to cytochrome bo oxidase electron transfer	5	35

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)	IC50 (µMol)	0.0045	0.0030	0.0115	0.0257	AID1102008; AID1105529
NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)	IC50 (µMol)	0.0050	0.0002	0.0022	0.0051	AID321744
Acyl carrier protein, mitochondrial	Bos taurus (cattle)	IC50 (µMol)	0.0050	0.0002	0.0022	0.0051	AID321744
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Peroxiredoxin-1	Homo sapiens (human)	Kd	2.6100	1.8300	2.2200	2.6100	AID1516530
Oxysterols receptor LXR-alpha	Homo sapiens (human)	Kd	3.2400	0.0924	3.1256	6.9700	AID1812739
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
mitochondrial respiratory chain complex I assembly	NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)
transmembrane transport	NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)
mitochondrial electron transport, NADH to ubiquinone	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
transmembrane transport	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
mitochondrial electron transport, NADH to ubiquinone	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
fatty acid biosynthetic process	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
mitochondrial respiratory chain complex I assembly	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
[2Fe-2S] cluster assembly	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
transmembrane transport	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
hydrogen peroxide catabolic process	Peroxiredoxin-1	Homo sapiens (human)
skeletal system development	Peroxiredoxin-1	Homo sapiens (human)
canonical NF-kappaB signal transduction	Peroxiredoxin-1	Homo sapiens (human)
cell population proliferation	Peroxiredoxin-1	Homo sapiens (human)
natural killer cell activation	Peroxiredoxin-1	Homo sapiens (human)
regulation of stress-activated MAPK cascade	Peroxiredoxin-1	Homo sapiens (human)
erythrocyte homeostasis	Peroxiredoxin-1	Homo sapiens (human)
natural killer cell mediated cytotoxicity	Peroxiredoxin-1	Homo sapiens (human)
hydrogen peroxide catabolic process	Peroxiredoxin-1	Homo sapiens (human)
fibroblast proliferation	Peroxiredoxin-1	Homo sapiens (human)
regulation of non-canonical NF-kappaB signal transduction	Peroxiredoxin-1	Homo sapiens (human)
removal of superoxide radicals	Peroxiredoxin-1	Homo sapiens (human)
cell redox homeostasis	Peroxiredoxin-1	Homo sapiens (human)
leukocyte activation	Peroxiredoxin-1	Homo sapiens (human)
response to oxidative stress	Peroxiredoxin-1	Homo sapiens (human)
cellular response to stress	Peroxiredoxin-1	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Oxysterols receptor LXR-alpha	Homo sapiens (human)
hormone-mediated signaling pathway	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of macrophage derived foam cell differentiation	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of triglyceride biosynthetic process	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of cholesterol efflux	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of cholesterol storage	Oxysterols receptor LXR-alpha	Homo sapiens (human)
intracellular receptor signaling pathway	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of lipid transport	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of cholesterol transport	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of transporter activity	Oxysterols receptor LXR-alpha	Homo sapiens (human)
response to progesterone	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of toll-like receptor 4 signaling pathway	Oxysterols receptor LXR-alpha	Homo sapiens (human)
phosphatidylcholine acyl-chain remodeling	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cholesterol homeostasis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
regulation of circadian rhythm	Oxysterols receptor LXR-alpha	Homo sapiens (human)
mRNA transcription by RNA polymerase II	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of macrophage activation	Oxysterols receptor LXR-alpha	Homo sapiens (human)
apoptotic cell clearance	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of fatty acid biosynthetic process	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of proteolysis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of DNA-templated transcription	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of lipid biosynthetic process	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of pinocytosis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of inflammatory response	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of lipoprotein lipase activity	Oxysterols receptor LXR-alpha	Homo sapiens (human)
positive regulation of protein metabolic process	Oxysterols receptor LXR-alpha	Homo sapiens (human)
lipid homeostasis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
sterol homeostasis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of type II interferon-mediated signaling pathway	Oxysterols receptor LXR-alpha	Homo sapiens (human)
triglyceride homeostasis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cellular response to lipopolysaccharide	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of pancreatic juice secretion	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of secretion of lysosomal enzymes	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of cold-induced thermogenesis	Oxysterols receptor LXR-alpha	Homo sapiens (human)
negative regulation of response to endoplasmic reticulum stress	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cell differentiation	Oxysterols receptor LXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
NADH dehydrogenase (ubiquinone) activity	NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)
NADH dehydrogenase (ubiquinone) activity	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
FMN binding	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
metal ion binding	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
NAD binding	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
4 iron, 4 sulfur cluster binding	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
fatty acid binding	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
NADH dehydrogenase (ubiquinone) activity	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
oxidoreductase activity	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
mitochondrial large ribosomal subunit binding	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
RNA binding	Peroxiredoxin-1	Homo sapiens (human)
peroxidase activity	Peroxiredoxin-1	Homo sapiens (human)
protein binding	Peroxiredoxin-1	Homo sapiens (human)
thioredoxin peroxidase activity	Peroxiredoxin-1	Homo sapiens (human)
identical protein binding	Peroxiredoxin-1	Homo sapiens (human)
cadherin binding	Peroxiredoxin-1	Homo sapiens (human)
transcription cis-regulatory region binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
transcription cis-regulatory region binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Oxysterols receptor LXR-alpha	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Oxysterols receptor LXR-alpha	Homo sapiens (human)
DNA binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
nuclear receptor activity	Oxysterols receptor LXR-alpha	Homo sapiens (human)
protein binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
zinc ion binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cholesterol binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
chromatin DNA binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
sterol response element binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Oxysterols receptor LXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mitochondrial inner membrane	NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)
respiratory chain complex I	NADH-ubiquinone oxidoreductase chain 1	Bos taurus (cattle)
mitochondrial inner membrane	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
respiratory chain complex I	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Bos taurus (cattle)
mitochondrial matrix	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
mitochondrial membrane	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
respiratory chain complex I	Acyl carrier protein, mitochondrial	Bos taurus (cattle)
extracellular space	Peroxiredoxin-1	Homo sapiens (human)
nucleus	Peroxiredoxin-1	Homo sapiens (human)
cytoplasm	Peroxiredoxin-1	Homo sapiens (human)
cytosol	Peroxiredoxin-1	Homo sapiens (human)
melanosome	Peroxiredoxin-1	Homo sapiens (human)
extracellular exosome	Peroxiredoxin-1	Homo sapiens (human)
cytosol	Peroxiredoxin-1	Homo sapiens (human)
nucleus	Oxysterols receptor LXR-alpha	Homo sapiens (human)
nucleoplasm	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cytoplasm	Oxysterols receptor LXR-alpha	Homo sapiens (human)
cytosol	Oxysterols receptor LXR-alpha	Homo sapiens (human)
RNA polymerase II transcription regulator complex	Oxysterols receptor LXR-alpha	Homo sapiens (human)
chromatin	Oxysterols receptor LXR-alpha	Homo sapiens (human)
receptor complex	Oxysterols receptor LXR-alpha	Homo sapiens (human)
nucleus	Oxysterols receptor LXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (132)

Assay ID	Title	Year	Journal	Article
AID1812661	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as decrease in FXR mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812691	Induction of apoptosis in human HepG2 cells assessed as change in caspase 3 protein expression at 1 to 5 uM after 48 hrs	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812702	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as fold increase in liver LDL-cholesterol level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812698	Toxicity in HCD-fed C57BL/6 mouse assessed as fold increase in ALT level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1105527	Inhibition of Solanum tuberosum (potato) inner mitochondrial membrane NDH2 assessed as deaminoNADH-DB reductase activity at 100 uM relative to control	1996	Biochimica et biophysica acta, Jan-11, Volume: 1273, Issue:1	Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases.
AID1490951	Antiproliferative activity against human SW480 cells after 48 hrs by MTT assay	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1812672	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as liver necrosis at 0.8 mg/kg, ip by histological analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516511	Down regulation of SLC2A1 mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812712	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as down regulation of Ost-alpha mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID610730	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using AzQ1 as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1812700	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as fold increase in liver total cholesterol level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812686	Induction of mitochondrial dysfunction in human HepG2 cells assessed as increase in ROS production at 0.1 to 5 uM after 48 hrs by flow cytometric analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812666	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on visceral coefficient of lung at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812681	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as change in IL-1beta level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812737	Down regulation of Cyp7a1 mRNA expression level in human HepG2 cells at 5 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516517	Antioxidant activity in human ACHN cells harboring shPRDX1 gene assessed as reduction in reactive oxygen species level at 25 to 50 nM measured after 24 hrs by Cell-rox reagent-based flow cytometry	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812722	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as decrease in Car mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812706	Reversal of HCD-induced LXRalpha activation in C57BL/6 mouse assessed as decrease in LXRalpha protein level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812743	Toxicity in mouse assessed as death at 10 mg/kg, po after 45 mins	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812718	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as change in Ugt1a1 mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812729	Down regulation of SHP mRNA level in human HepG2 cells at 5 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812726	Down regulation of FXR mRNA level in human HepG2 cells at 1 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516503	Cytotoxicity against human OS-RC2 cells assessed as reduction in cell viability measured after 72 hrs by CCK8 assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516508	Down regulation of SOD2 mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812665	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on visceral coefficient of spleen at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID610764	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using DMB as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1812736	Down regulation of Cyp7a1 mRNA expression level in human HepG2 cells at 1 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812671	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as white discoloration of liver at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812680	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as change in IL-6 level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812664	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on visceral coefficient of liver at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID321744	Inhibition of NADH-ubiquinone oxidoreductase assessed as NADH oxidase activity in bovine heart submitochondrial particles	2008	Bioorganic & medicinal chemistry, Feb-15, Volume: 16, Issue:4	Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.
AID1516512	Down regulation of LDHA mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812687	Induction of apoptosis in human HepG2 cells assessed as live cells at 5 uM measured after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 84.5 %)	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812732	Induction of LDLR mRNA level in human HepG2 cells assessed as fold increase in LDLR expression at 1 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812675	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as appearance of pyknotic nucleus at 0.8 mg/kg, ip by histological analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516533	Toxicity in Balb/c nu/nu mouse xenografted with human ACHN cells assessed as effect on survival at 0.8 mg/kg, ip administered once daily for 21 days	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID610765	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using DAzB as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1516510	Down regulation of HK2 mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812719	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as fold increase in LXRalpha mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812703	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as fold increase in plasma LDL-cholesterol level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1347682	Inhibition of wild-type Yersinia pseudotuberculosis T3SS-mediated YopE secretion at 71 uM after 2 hrs under low calcium medium by SDS-PAGE analysis relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Investigation of the Physical and Bioactive Properties of Bromo- and Iodo-Containing Sponge-Derived Compounds Possessing an Oxyphenylethanamine Core.
AID1105526	Inhibition of Escherichia coli GR19N NDH1 assessed as deaminoNADH-DB reductase activity	1996	Biochimica et biophysica acta, Jan-11, Volume: 1273, Issue:1	Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases.
AID1812668	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as fold increase in plasma ALT at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516526	Induction of apoptosis in human ACHN cells assessed as necrotic cells at 50 nM measured after 48 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812674	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as large scale necrotic foci at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516523	Induction of apoptosis in human ACHN cells assessed as viable cells at 50 nM measured after 48 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 99.9%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516502	Cytotoxicity against human ACHN cells assessed as reduction in cell viability measured after 72 hrs by CCK8 assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812705	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as fold increase in plasma total bile acid level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812707	Inhibition of FXR protein expression level in HCD-fed C57BL/6 mouse at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812693	Induction of calcium signal in human HepG2 cells at 5 uM by Fluo-4AM dye based fluorescence assay	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812673	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as lipid accumulation in liver at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812688	Induction of apoptosis in human HepG2 cells assessed as early apoptotic cells at 5 uM measured after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 15.5 %)	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516513	Down regulation of MET mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812667	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on visceral coefficient of kidney at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812679	Toxicity in renal carcinoma xenografted C57BL/6 mouse kidney assessed as change in BUN level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516514	Down regulation of HIF1A mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812710	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as reduction in Ntcp-mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812727	Down regulation of SHP mRNA level in human HepG2 cells at 1 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812663	Toxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on visceral coefficient of heart at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812740	Drug concentration in mouse liver at 10 mg/kg, po after 30 mins by LC-MS/MS analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516507	Down regulation of EGFR mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516504	Cytotoxicity against human 786-O cells assessed as reduction in cell viability measured after 72 hrs by CCK8 assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812725	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability at < 10 uM incubated for 48 hrs by MTT assay	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516515	Up regulation of PRDX1 mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516521	Induction of apoptosis in human ACHN cells assessed as late apoptotic cells at 50 nM measured after 24 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516539	Antitumor activity against human ACHN cells xenografted in Balb/c nu/nu mouse assessed as tumor growth inhibition at 0.8 mg/kg, ip administered once daily for 21 days measured post-last dose by TUNEL staining-based assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1490949	Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1516516	Activation of PRDX1 in human ACHN cells assessed as reduction in reactive oxygen species level at 25 to 50 nM measured after 24 hrs by Cell-rox reagent-based flow cytometry	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516524	Induction of apoptosis in human ACHN cells assessed as early apoptotic cells at 50 nM measured after 48 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812739	Binding affinity to full-length human LXRalpha by surface plasmon resonance assay	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812669	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as fold increase in plasma AST at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516505	Cytotoxicity against human HK2 cells assessed as reduction in cell viability measured after 72 hrs by CCK8 assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1424122	Inhibition of type 3 secretion system protein secretion in Yersinia pseudotuberculosis at 30 ug/ml incubated for 2 hrs by SDS-PAGE and densitometric analysis	2017	Journal of natural products, 04-28, Volume: 80, Issue:4	Antibacterial Compounds from Marine Bacteria, 2010-2015.
AID1516522	Induction of apoptosis in human ACHN cells assessed as necrotic cells at 50 nM measured after 24 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812682	Induction of Cholesterol accumulation in human HepG2 cells assessed as fold increase in LDL-cholesterol level at 5 uM after 48 hrs	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516538	Up regulation of PRDX1 mRNA expression in human ACHN cells xenografted Balb/c nu/nu mouse at 0.8 mg/kg, ip administered once daily for 21 days measured post-last dose by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1490954	Induction of autophagosome accumulation in human HeLa cells harboring RFP-GFP-LC3 assessed as GFP-LC3 puncta formation at 30 uM after 24 hrs by DAPI staining based fluorescence microscopic method	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1490953	Antiproliferative activity against human U2OS cells after 48 hrs by MTT assay	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1516509	Down regulation of ETS1 mRNA expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by qRT-PCR analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516529	Induction of PRDX1 nuclear translocation in human ACHN cells at 25 to 50 nM measured after 24 hrs by DAPI staining-based microscopic analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812689	Induction of apoptosis in human HepG2 cells assessed as late apoptotic cells at 5 uM measured after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 0 %)	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812694	Induction of hepatic pathological changes in normal chow diet fed C57BL/6 mouse at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812720	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as reversal of LXRbeta mRNA upregulation by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812723	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as change in Car protein expression	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812697	Toxicity in HCD-fed C57BL/6 mouse assessed as body weight loss at 0.8 mg/kg, ip measured on day 28	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516527	Selectivity ratio of IC50 for cytotoxicity against human ACHN cells harboring shPRDX1 gene to IC50 for Cytotoxicity against human ACHN cells	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516519	Induction of apoptosis in human ACHN cells assessed as viable cells at 50 nM measured after 24 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 100%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516535	Toxicity in Balb/c nu/nu mouse xenografted with human ACHN cells assessed as decrease in body weight at 0.8 mg/kg, ip administered once daily for 21 days	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516525	Induction of apoptosis in human ACHN cells assessed as late apoptotic cells at 50 nM measured after 48 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812716	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as inhibition of Cyp7a1 mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID610727	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using Q0 as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1490956	Induction of autophagosome accumulation in human HeLa cells harboring RFP-GFP-LC3 assessed as increase in LC3-2 level after 24 hrs by immunoblot method	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1812676	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as inflammatory infiltration at 0.8 mg/kg, ip by histological analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812670	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as liver swelling at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812677	Toxicity in renal carcinoma xenografted C57BL/6 mouse kidney assessed as change in CRE level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1490952	Antiproliferative activity against human HL60 cells after 48 hrs by EZ-Cytox cell viability assay	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1812685	Induction of mitochondrial dysfunction in human HepG2 cells assessed as decrease in TNFalpha level at 1 uM after 48 hrs	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1105525	Inhibition of Escherichia coli GR19N NDH2 assessed as deaminoNADH-DB reductase activity at 100 uM relative to control	1996	Biochimica et biophysica acta, Jan-11, Volume: 1273, Issue:1	Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases.
AID1516528	Up regulation of nuclear PRDX1 expression in human ACHN cells at 25 to 50 nM measured after 24 hrs by immunoblot analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1105528	Inhibition of Solanum tuberosum (potato) submitochondrial particle NDH1 assessed as deaminoNADH-DB reductase activity	1996	Biochimica et biophysica acta, Jan-11, Volume: 1273, Issue:1	Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases.
AID1812738	Cmax in mouse at 10 mg/kg, po by LC-MS/MS analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID321749	Cytotoxicity against mouse L929 fibroblasts	2008	Bioorganic & medicinal chemistry, Feb-15, Volume: 16, Issue:4	Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.
AID1812715	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as change in Mrp2 mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1490950	Antiproliferative activity against human HeLa cells after 48 hrs by MTT assay	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1516518	Antiproliferative activity against human ACHN cells assessed as inhibition of cell proliferation at 50 nM measured after 24 to 72 hrs by holographic microscopy	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1105529	Inhibition of Bos taurus (bovine) heart submitochondrial particle NDH1 assessed as NADH-DB reductase activity	1996	Biochimica et biophysica acta, Jan-11, Volume: 1273, Issue:1	Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases.
AID1516531	Antitumor activity against human ACHN cells xenografted in Balb/c nu/nu mouse assessed as tumor weight at 0.8 mg/kg, ip administered once daily for 21 days measured post-last dose by caliper method (Rvb = 0.55 +/- 0.13 g)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812699	Toxicity in HCD-fed C57BL/6 mouse assessed as fold increase in AST level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812711	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as down regulation of Oatp1 mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812714	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as change in Bsep mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516530	Binding affinity to full-length human PRDX1 by surface plasmon resonance analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812692	Induction of mitochondrial membrane potential loss in human HepG2 cells assessed as intact mitochondrial membrane potential at 5 uM after 48 hrs by TMRM dye based flow cytometric analysis (Rvb = 74.2%)	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516520	Induction of apoptosis in human ACHN cells assessed as early apoptotic cells at 50 nM measured after 24 hrs by Annexin V-FITC/propidium iodide staining based flow cytometry (Rvb = 0%)	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1516506	Cytotoxicity against human ACHN cells harboring shPRDX1 gene assessed as reduction in cell viability measured after 72 hrs by CCK8 assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID610729	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using Q1 as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1812724	Effect on bile acid homeostasis in Chow diet-fed C57BL/6 mouse assessed as change in Car protein expression	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1490948	Inhibition of ascorbic acid/methylene blue activated recombinant human IDO expressed in Escherichia coli up to 10 uM using L-Tryptophan as substrate after 60 mins by spectrophotometric method relative to control	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1812695	Induction of histopathological changes in HCD-fed C57BL/6 mouse assessed as striking subcapsular foci at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812696	Induction of histopathological changes in HCD-fed C57BL/6 mouse assessed as swelling gallbladder size at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812733	Induction of LDLR mRNA level in human HepG2 cells assessed as fold increase in LDLR expression at 5 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812690	Induction of apoptosis in human HepG2 cells assessed as necrotic cells at 5 uM measured after 48 hrs by Annexin-V-FITC/propidium iodide staining based flow cytometry (Rvb = 0 %)	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812701	Induction of HCD-induced cholestasis in C57BL/6 mouse assessed as fold increase in liver total bile acid level at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812721	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as change in Ppar-alpha mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1516540	Antitumor activity against human ACHN cells xenografted in Balb/c nu/nu mouse assessed as tumor growth inhibition at 0.8 mg/kg, ip administered once daily for 21 days measured post-last dose by H and E staining-based assay	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1812678	Induction of histopathological changes in HCD-fed C57BL/6 mouse assessed as white discoloration of liver at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812662	Hepatotoxicity in renal carcinoma xenografted C57BL/6 mouse assessed as effect on body weight at 0.8 mg/kg, ip	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1812717	Effect on bile acid homeostasis in HCD-fed C57BL/6 mouse assessed as inhibition of Cyp8b1 mRNA expression by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID610728	Inhibition of Rhodobacter capsulatus NADH-ubiquinone oxidoreductase using AzQ0 as substrate	2010	Bioorganic & medicinal chemistry, May-15, Volume: 18, Issue:10	Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.
AID1812728	Down regulation of FXR mRNA level in human HepG2 cells at 5 uM by RT-qPCR analysis	2021	Journal of medicinal chemistry, 07-22, Volume: 64, Issue:14	LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.
AID1490955	Induction of autophagosome accumulation in human HeLa cells harboring RFP-GFP-LC3 assessed as increase in p62 level after 24 hrs by immunoblot method	2017	Journal of natural products, 05-26, Volume: 80, Issue:5	Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
AID1516537	Up regulation of PRDX1 expression in human ACHN cells xenografted Balb/c nu/nu mouse at 0.8 mg/kg, ip administered once daily for 21 days measured post-last dose by immunoblot analysis	2019	Journal of medicinal chemistry, 08-08, Volume: 62, Issue:15	Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.
AID1102008	Inhibition of Bos taurus (bovine) mitochondrial complex 1 assessed as reduction in enzyme activity by NADH-HU oxidoreductase assay	2002	Biochimica et biophysica acta, Dec-02, Volume: 1556, Issue:2-3	Hybrid ubiquinone: novel inhibitor of mitochondrial complex I.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	7 (10.29)	18.7374
1990's	15 (22.06)	18.2507
2000's	17 (25.00)	29.6817
2010's	25 (36.76)	24.3611
2020's	4 (5.88)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (4.41%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	65 (95.59%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	2.03	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.13	1	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.08	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.41	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	7.05	1	metal allergen; nickel group element atom	epitope; micronutrient
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.08	1	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	1.95	1	barbiturates
2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone: ubiquinol analog. 6-decylubiquinone : A member of the class of 1,4-benzoquinones that is 2,3-dimethoxybenzoquinone which has been substituted at positions 5 and 6 by decyl and methyl groups.	2.05	1	1,4-benzoquinones	cofactor
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.15	1	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.41	1	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
nalidixic acid [no description available]	3.25	1	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
ubiquinone q1 Ubiquinone Q1: interacts with iron atom to form acceptor quinone complex. ubiquinone-1 : A compound composed of the standard 2,3-dimethoxy-5-methylbenzoquinone nucleus common to ubiquinones; and a side chain of a single isoprenoid unit.	2.47	2	ubiquinones
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.42	2	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
thenoyltrifluoroacetone Thenoyltrifluoroacetone: Chelating agent and inhibitor of cellular respiration.	8.48	2
adrenochrome Adrenochrome: Pigment obtained by the oxidation of epinephrine.	1.98	1	indoles
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	1.96	1	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.15	1	kanamycins	bacterial metabolite
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	3.25	1	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	5.36	22	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
phenformin Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis.	2.41	1	biguanides	antineoplastic agent; geroprotector; hypoglycemic agent
lauric acid diethanolamide lauric acid diethanolamide: component of shampoo implicated in contact dermatitis	3.25	1	fatty amide
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.17	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.45	2	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
rhein [no description available]	1.95	1	dihydroxyanthraquinone
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	1.98	1	dialdehyde	biomarker
galegine galegine: structure given in first source; from Verbesina encelioides and Gelega oficinalis plants; toxic to livestock	2.41	1	guanidines
2-methyl-1,4-benzoquinone cresoquinone: no further information available 6/2003	1.99	1
2,6-dichloro-4-nitrophenol [no description available]	1.99	1
carboxin Carboxin: A systemic agricultural fungicide and seed treatment agent.. carboxin : An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid. A fungicide for control of bunts and smuts that is normally used as a seed treatment.	3.05	1	anilide fungicide; anilide; enamide; organosulfur heterocyclic compound; oxacycle; secondary carboxamide	antifungal agrochemical; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor
tellurous acid tellurous acid: tellurite anion inhibits oxidation of NAD-linked substrates in kidney & liver mitochondria; RN given refers to parent cpd	1.95	1	tellurium oxoacid
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.13	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.96	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.17	1	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
etoposide [no description available]	7.04	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	7.67	3	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
atorvastatin [no description available]	2.31	1	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	1.97	1	D-glucopyranose	epitope; mouse metabolite
2,6-dimethyl-1,4-benzoquinone [no description available]	2.42	2
ubiquinone-o 2,3-dimethoxy-5-methyl-p-benzoquinone: from solid-cultured Antrodia camphorata; structure in first source. ubiquinone-0 : A derivative of benzoquinone carrying a 5-methyl substituent; and methoxy substituents at positions 2 and 3. The core structure of the ubiquinone group of compounds.	2.05	1	ubiquinones	Escherichia coli metabolite; human metabolite
coenzyme a [no description available]	2.13	1	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether: structure CF2=C(CF3)OCH2F; a vinyl ether	2.02	1	organofluorine compound
4-hydroxy-25-desoxyneorollinicin 4-hydroxy-25-desoxyneorollinicin: isol from Rollina papilionella; structure given in first source	3.25	6
actinopyrone a actinopyrone A: from Streptomyces; structure given in second source	1.96	1
sorafenib [no description available]	2.66	2	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
1',2'-dihydrorotenone 1',2'-dihydrorotenone: RN given refers to (2R-(2alpha,6aalpha,12aalpha))-isomer; structure given in first source	2	1
deoxynyboquinone deoxynyboquinone: structure in first source	3.25	1
squamocin squamocin: from seeds of Annona squamosa; a trihydroxy-bis-tetrahydrofuran fatty acid lactone; inhibits E. coli NADH:quinone oxidoreductase (NDH-1); structure given in first source	1.98	1	polyketide
gw 3965 GW 3965: a liver X receptor ligand	2.31	1	diarylmethane
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	3.25	1	actinomycin	mutagen
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	2.25	1	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	3.32	2	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
nadp [no description available]	2.43	2
8-azidoadenosine 5'-triphosphate [no description available]	1.96	1
methyl radical [no description available]	2.03	1	organic radical
brefeldin a [no description available]	2.13	1	macrolide antibiotic	Penicillium metabolite
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	1.95	1	chalcogen; metalloid atom
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	4.02	4	amidobenzoic acid
myxothiazol myxothiazol: strobilurin analogue; methoxyacrylamide derivative; antifungal antibiotic from Myxococcus fulvus; structure given in first source. myxothiazol : A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.	2.45	2
napyradiomycin a1 napyradiomycin A1: from culture broth Chainia rubra MG802-AF1; structure given in first source	3.25	1	menaquinones
fenpyroximate fenpyroximate: structure in first source	2.9	1	pyrazole acaricide; tert-butyl ester	mitochondrial NADH:ubiquinone reductase inhibitor
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.29	6	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.01	1	chlorophyll; methyl ester	cofactor
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	4.35	6
glucopiericidin a glucopiericidin A: from Streptomyces pactum S48727 as co-metabolite of piericidin A(1); structure given in first source; glycoside antibiotic	3.16	5
streptochlorin streptochlorin: inhibits both NF-kappaB activation and angiogenesis; isolated from marine Streptomyces; structure in first source	2.17	1
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	3.25	1	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	3.25	1
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	1.96	1
ikarugamycin ikarugamycin: structure given in first source; an antiprotozoal antibiotic isolated from Streptomyces phaeochromogenes ikaruganensis; inhibits the uptake of oxidized LDL in macrophage J774. ikarugamycin : A polyketide macrolactam containing a tetramic acid (pyrrolidine-2,4-dione) ring system. It is isolated from Streptomyces as an antibiotic with antiprotozoal and cytotoxic activities.	3.25	1
antimycin [no description available]	2.02	1
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.99	1
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.01	1
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	2.11	1
iodinin iodinin: antibiotic pigment from Chromobacterium iodinum; structure	3.25	1
aurodox Aurodox: Antibiotic obtained from a Streptomyces variant considered as possibly effective against Streptococcus pyogenes infections. It may promote growth in poultry.	2.1	1

Condition	Relationship Strength	Studies
Adenocarcinoma Of Kidney [description not available]	2.21	1
Cancer of Kidney [description not available]	2.21	1
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.21	1
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.21	1
Pleuropericarditis Inflammation of both the PERICARDIUM and the PLEURA.	2.31	1
Pericarditis Inflammation of the PERICARDIUM from various origins, such as infection, neoplasm, autoimmune process, injuries, or drug-induced. Pericarditis usually leads to PERICARDIAL EFFUSION, or CONSTRICTIVE PERICARDITIS.	2.31	1
Chronic Lung Injury [description not available]	2.08	1
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.1	1
Hereditary Optic Neuroretinopathy [description not available]	2.13	1
Optic Atrophy, Hereditary, Leber A maternally linked genetic disorder that presents in mid-life as acute or subacute central vision loss leading to central scotoma and blindness. The disease has been associated with missense mutations in the mtDNA, in genes for Complex I, III, and IV polypeptides, that can act autonomously or in association with each other to cause the disease. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/Omim/, MIM#535000 (April 17, 2001))	2.13	1
Carcinoma, Thymic [description not available]	2.01	1
Thymoma A neoplasm originating from thymic tissue, usually benign, and frequently encapsulated. Although it is occasionally invasive, metastases are extremely rare. It consists of any type of thymic epithelial cell as well as lymphocytes that are usually abundant. Malignant lymphomas that involve the thymus, e.g., lymphosarcoma, Hodgkin's disease (previously termed granulomatous thymoma), should not be regarded as thymoma. (From Stedman, 25th ed)	2.01	1
Cancer of Colon [description not available]	2.04	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.04	1

piericidin a

Description

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Overview

Roles (4)

Drug Classes (4)

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Protein Targets (5)

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Biological Processes (57)

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Studies (68)

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Research Demand Index: 32.98

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piericidin a

Description

Cross-References

Synonyms (41)

Research Excerpts

Overview

Roles (4)

Drug Classes (4)

Pathways (10)

Protein Targets (5)

Inhibition Measurements

Activation Measurements

Biological Processes (57)

Molecular Functions (24)

Ceullar Components (14)

Bioassays (132)

Research

Studies (68)

Market Indicators

Research Demand Index: 32.98

Study Types

Related Drugs (76)

Related Conditions (14)