MiMeDB: Showing metabocard for Piceatannol (MMDBc0033705)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:59:43 UTC

Update Date

2022-08-31 22:37:54 UTC

Metabolite ID

MMDBc0033705

Metabolite Identification

Common Name

Piceatannol

Description

3,3',4'5-Tetrahydroxystilbene (or Piceatannol) is a phenolic stilbenoid. It is a metabolite of resveratrol found in red wine. A viral protein-tyrosine kinase (LMP2A) implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus, was recently found to be blocked by picetannol in vitro (PMID 2590224 ). Therefore there is research interest in piceatannol as an anti-cancer and anti-EBV drug. Piceatannol can also act as an agonist for estrogen receptor alpha in human breast cancer cells (PMID: 16216908 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₄H₁₂O₄

Average Mass

244.246

Monoisotopic Mass

244.073558866

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

10083-24-6

SMILES

Not Available

InChI Identifier

InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

InChI Key

CDRPUGZCRXZLFL-OWOJBTEDSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Placenta
Platelet

Tissue Locations

Placenta
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo_sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

Not Available

General References

Geahlen RL, McLaughlin JL: Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem Biophys Res Commun. 1989 Nov 30;165(1):241-5. doi: 10.1016/0006-291x(89)91060-7. [PubMed:2590224 ]
Palmieri L, Mameli M, Ronca G: Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. Drugs Exp Clin Res. 1999;25(2-3):79-85. [PubMed:10370868 ]
Minuz P, Gaino S, Zuliani V, Tommasoli RM, Benati D, Ortolani R, Zancanaro C, Berton G, Santonastaso CL: Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha. Thromb Haemost. 2002 May;87(5):888-98. [PubMed:12038794 ]
Maggiolini M, Recchia AG, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S: The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells. J Mol Endocrinol. 2005 Oct;35(2):269-81. doi: 10.1677/jme.1.01783. [PubMed:16216908 ]

Showing metabocard for Piceatannol (MMDBc0033705)

MOL for #<Metabolite:0x00007f121128b2a0>

3D MOL for #<Metabolite:0x00007f121128b2a0>

3D SDF for #<Metabolite:0x00007f121128b2a0>

3D-SDF for #<Metabolite:0x00007f121128b2a0>

PDB for #<Metabolite:0x00007f121128b2a0>

3D PDB for #<Metabolite:0x00007f121128b2a0>

SMILES for #<Metabolite:0x00007f121128b2a0>

INCHI for #<Metabolite:0x00007f121128b2a0>

Structure for #<Metabolite:0x00007f121128b2a0>

3D Structure for #<Metabolite:0x00007f121128b2a0>