Details of the Drug

General Information of Drug (ID: DMYOP45)

Drug Name

Piceatannol

Synonyms

piceatannol; 10083-24-6; 3-Hydroxyresveratol; piceatanol; astringinin; 3,5,3',4'-Tetrahydroxystilbene; (E)-4-(3,5-dihydroxystyryl)benzene-1,2-diol; 3,3',4'5-Tetrahydroxystilbene; 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol; 3,3',4,5'-Tetrahydroxystilbene; UNII-6KS3LS0D4F; NSC 365798; NSC-365798; NSC 622471; 6KS3LS0D4F; CHEMBL69863; 3,3',4,5'-Stilbenetetrol; 4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,2-diol; 4339-71-3; CHEBI:28814; C14H12O4; NSC365798; NSC622471; 1,2-Benzenediol, 4-(2-(3,5-dihydroxyphenyl)ethenyl)-

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

244.24

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C14H12O4
IUPAC Name: 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Canonical SMILES: C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O)O)O)O
InChI: 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+
InChIKey: CDRPUGZCRXZLFL-OWOJBTEDSA-N

Cross-matching ID

PubChem CID: 667639
ChEBI ID: CHEBI:28814
CAS Number: 10083-24-6
DrugBank ID: DB08399
TTD ID: D0O0VZ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Interferon regulatory factor 3 (IRF3)	TTYR7OH	IRF3_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2)	OT02MSKN	3BHS2_HUMAN	Gene/Protein Processing	[2]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Protein Interaction/Cellular Processes	[3]
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[4]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[5]
Biotin--protein ligase (HLCS)	OTPDUX30	BPL1_HUMAN	Gene/Protein Processing	[6]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[7]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[8]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[8]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[9]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Inhibition of lipopolysaccharide-induced interferon regulatory factor 3 activation and protection from septic shock by hydroxystilbenes. Shock. 2004 May;21(5):470-5.
2	Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs. Prostate. 2014 Jun;74(8):839-51.
3	Resveratrol promotes clearance of Alzheimer's disease amyloid-beta peptides. J Biol Chem. 2005 Nov 11;280(45):37377-82.
4	Hydroxystilbenes and methoxystilbenes activate human aryl hydrocarbon receptor and induce CYP1A genes in human hepatoma cells and human hepatocytes. Food Chem Toxicol. 2017 May;103:122-132.
5	Induction of autophagy, apoptosis and aquisition of resistance in response to piceatannol toxicity in MOLT-4 human leukemia cells. Toxicol In Vitro. 2019 Sep;59:12-25. doi: 10.1016/j.tiv.2019.03.040. Epub 2019 Mar 30.
6	Resveratrol compounds inhibit human holocarboxylase synthetase and cause a lean phenotype in Drosophila melanogaster. J Nutr Biochem. 2015 Nov;26(11):1379-84. doi: 10.1016/j.jnutbio.2015.07.004. Epub 2015 Jul 26.
7	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. 2001 Nov;15(11):1735-42. doi: 10.1038/sj.leu.2402284.
8	Tumor-specificity and apoptosis-inducing activity of stilbenes and flavonoids. Anticancer Res. 2005 May-Jun;25(3B):2055-63.
9	Involvement of SIRT1 in hypoxic down-regulation of c-Myc and beta-catenin and hypoxic preconditioning effect of polyphenols. Toxicol Appl Pharmacol. 2012 Mar 1;259(2):210-8.
10	Natural products induce a G protein-mediated calcium pathway activating p53 in cancer cells. Toxicol Appl Pharmacol. 2015 Nov 1;288(3):453-62. doi: 10.1016/j.taap.2015.08.016. Epub 2015 Sep 1.