Page last updated: 2024-12-07

picein

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Picein is a natural phenolic compound found in various plants, notably grapevine, blueberry, and hawthorn. It is a glycosylated derivative of resveratrol, a well-known polyphenol with antioxidant and anti-inflammatory properties. Picein is characterized by its high antioxidant activity, which is attributed to its ability to scavenge free radicals and inhibit oxidative stress. Research suggests that picein possesses a range of biological effects, including anti-inflammatory, anti-cancer, neuroprotective, and cardioprotective activities. It is being studied for its potential therapeutic applications in various diseases, such as cardiovascular disease, diabetes, and neurodegenerative disorders. Picein is synthesized through the glycosylation of resveratrol, a process that involves the attachment of a sugar molecule to the resveratrol molecule. The glycosylation process enhances the water solubility and bioavailability of picein, making it more readily absorbed and utilized by the body. The importance of picein lies in its potential to offer a natural and safe alternative to synthetic drugs for the treatment of various diseases. Its wide range of biological activities and its natural origin make it an attractive target for research and development.'

picein: RN given refers to (beta-D)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID92123
CHEMBL ID1512620
CHEBI ID8199
SCHEMBL ID467772
MeSH IDM0145041

Synonyms (50)

Synonym
ameliaroside
picein
530-14-3
smr001397077
MLS002472970
1-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
NCGC00247461-01
chebi:8199 ,
CHEMBL1512620
1-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]ethanone
A829354
HMS2192O04
1-(4-(beta-d-glucopyranosyloxy)phenyl)ethan-1-one
2h3act49cq ,
unii-2h3act49cq
einecs 208-473-7
l-picein
salicinerein
salinigrin
p-hydroxyacetophenone-d-glucoside
piceoside
4-acetylphenyl beta-d-glucopyranoside
SCHEMBL467772
W-203003
4-acetylphenyl-b-d-glucopyranoside
GOZCEKPKECLKNO-RKQHYHRCSA-N
ethanone, 1-[4-(.beta.-d-glucopyranosyloxy)phenyl]-
p-acetylphenyl-.beta.-d-glucoside
piccin
1194723-63-1
ethanone, 1-(4-(.beta.-d-glucopyranosyloxy)phenyl)-
4-acetylphenyl .beta.-d-glucopyranoside
picein [mi]
1-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]ethanone
mfcd00016916
picein, analytical standard
1-[4-(beta-d-glucopyranosyloxy)phenyl]ethanone
AKOS027446727
1192351-89-5
NCGC00247461-02
1-(4-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)phenyl)ethanone
Q7190609
1-(4-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)phenyl)ethanone
4-acetylphenyl ?-d-glucopyranoside
4-acetylphenyl beta -d-glucopyranoside
1-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethan-1-one
HY-N8698
CS-0148944
DTXSID201031535
FS-6834

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[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]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
chromobox protein homolog 1Homo sapiens (human)Potency3.16230.006026.168889.1251AID540317
eyes absent homolog 2 isoform aHomo sapiens (human)Potency11.22021.199814.641950.1187AID488837
gemininHomo sapiens (human)Potency0.00520.004611.374133.4983AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID1193392Cytotoxicity against human HepG 2.2.15 cells by MTT assay2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
AID1101815Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of seed respiration during germination after 24 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101840Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of seed germination after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1193397Antiviral activity against hepatitis B viral in human HepG2.2.15 cells assessed as decrease in viral DNA replication treated for 7 days by real time PCR analysis2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
AID1101816Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of seed respiration during germination after 24 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101834Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of shoot development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101833Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of root development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101806Inhibition of H+ uptake in Spinacia oleracea (spinach) chloroplasts2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101803Antioxidant activity assessed as DPPH free radical scavenging activity after 30 min by TLC autographic assay2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101827Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of seed germination at > 500 uM after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101823Increase of shoot development during seeding stage in Trifolium pratense (red clover) at 200 uM after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101809Increase of seed respiration during germination in Lolium multiflorum (Italian ryegrass)at 30 uM2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101835Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of root development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101812Phytotoxicity against Physalis ixocarpa assessed as inhibition of seed respiration during germination after 24 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101821Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of seed germination at 500 uM after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101829Phytotoxicity against Trifolium pratense (red clover) assessed as inhibition of root development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101832Phytotoxicity against Physalis ixocarpa assessed as inhibition of shoot development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101831Phytotoxicity against Physalis ixocarpa assessed as inhibition of root development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101824Increase of shoot development during seeding stage in Physalis ixocarpa up to 50 uM after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101839Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of seed germination after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1193393Antiviral activity against hepatitis B viral in human HepG2.2.15 cells assessed as surface antigen HBsAg secretion after 72 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
AID1193395Antiviral activity against hepatitis B viral in human HepG2.2.15 cells assessed as surface antigen HBeAg secretion after 72 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
AID1101836Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of shoot development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101830Phytotoxicity against Trifolium pratense (red clover) assessed as inhibition of shoot development during seeding stage after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101837Phytotoxicity against Trifolium pratense (red clover) assessed as inhibition of seed germination after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101828Phytotoxicity against Lactuca sativa (lettuce) assessed as inhibition of seed germination at > 500 uM after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101808Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of seed respiration during germination at 300 to 500 uM after 24 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101826Increase of root development during seeding stage in Lactuca sativa (lettuce) at 50 to 300 uM after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID614278Antiinflammatory activity in rat HAPI cells assessed as inhibition of LPS-induced iNOS mRNA expression at 50 uM treated 30 mins before LPS challenge measured after 6 hrs by RT-PCR analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Inhibitory effects of chalcone glycosides isolated from Brassica rapa L. 'hidabeni' and their synthetic derivatives on LPS-induced NO production in microglia.
AID1101838Phytotoxicity against Physalis ixocarpa assessed as inhibition of seed germination after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101825Increase of root development during seeding stage in Trifolium pratense (red clover) at 50 to 300 uM after 120 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1193398Selectivity index, ratio of CC50 for human HepG2.2.15 cells to IC50 for decrease in hepatitis B viral DNA replication in human HepG2(2.2.15) cells2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
AID1101822Phytotoxicity against Lolium multiflorum (Italian ryegrass) assessed as inhibition of seed germination at 500 uM after 48 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID1101810Phytotoxicity against Trifolium pratense (red clover) assessed as inhibition of seed respiration during germination after 24 hr2002Journal of agricultural and food chemistry, Apr-10, Volume: 50, Issue:8
Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.67)18.7374
1990's2 (13.33)18.2507
2000's1 (6.67)29.6817
2010's7 (46.67)24.3611
2020's4 (26.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.60

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.60 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index5.19 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]