Structure Database (LMSD)

Common Name
Piceatannol
Systematic Name
Synonyms
  • 3,3',4'5-tetrahydroxystilbene
LM ID
LMPK13090006
Formula
C14H12O4
Exact Mass
Calculate m/z
244.07356
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]

Biological Context

Piceatannol is a stilbene that has been found in red wine and an active metabolite of trans-resveratrol , a polyphenol with diverse biological activities.1 It is formed from trans-resveratrol by the cytochrome P450 (CYP) isoform CYP1B1.1,2 Piceatannol induces apoptosis in BJAB B cell lymphoma cells (EC50 = 25 µM).3 Dietary administration of piceatannol (0.025% w/w) improves intestinal epithelial barrier integrity, prevents decreases in colon length, and increases body weight in a mouse model of ulcerative colitis induced by dextran sodium sulfate (DSS).4

This information has been provided by Cayman Chemical

References

1. Potter, G.A., Patterson, L.H., Wanogho, E., et al. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYPIBI. Br. J. Cancer 86(5), 774-778 (2002).
2. Rotondo, S., Rajtar, G., Manarini, S., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. Br. J. Pharmacol. 123(8), 1691-1699 (1998).
3. Wieder, T., Prokop, A., Bagci, B., et al. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts. Leukemia 15(11), 1735-1742 (2001).
4. Lin, W.-S., Chueh, T.-L., Nagabhushanam, K., et al. Piceatannol and 3'-hydroxypterostilbene alleviate inflammatory bowel disease by maintaining intestinal epithelial integrity and regulating gut microbiota in mice. J. Agric. Food Chem. 71(4), 1994-2005 (2023).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Picea abies (#3329)
Pinopsida (#58019)
The constitution of piceatannol,
J Chem Soc, 1963

String Representations

InChiKey (Click to copy)
CDRPUGZCRXZLFL-OWOJBTEDSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
C1=C(O)C=C(/C=C/C2=CC(O)=C(O)C=C2)C=C1O

Other Databases

Wikipedia
Piceatannol
KEGG ID
C05901
HMDB ID
HMDB0004215
CHEBI ID
28814
PubChem CID
667639
Cayman ID
10009366
PDB ID
PIT

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 2
Aromatic Rings 2
Rotatable Bonds 2
Van der Waals Molecular Volume 220.92
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 2.68
Molar Refractivity 68.47

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Created at
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Updated at
5th Feb 2022