NAV

Piceatannol

Identification

Generic Name
Piceatannol
DrugBank Accession Number
DB08399
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 244.246
Monoisotopic: 244.073558866
Chemical Formula
C14H12O4
Synonyms
  • 3-hydroxyresveratol
  • 3,3',4,5'-Tetrahydroxystilbene
  • 3,3',4'5-Tetrahydroxystilbene
  • 3,5,3',4'-tetrahydroxystilbene
  • 4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,2-diol
  • Piceatannol
External IDs
  • C05901
  • DB08399
  • J61.264B
  • NSC-365798
  • NSC-622471
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UATP synthase subunit alpha, mitochondrialNot AvailableHumans
UATP synthase subunit beta, mitochondrialNot AvailableHumans
UATP synthase subunit gamma, mitochondrialNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Piceatannol.
CarbimazoleThe therapeutic efficacy of Carbimazole can be decreased when used in combination with Piceatannol.
FollitropinThe therapeutic efficacy of Follitropin can be decreased when used in combination with Piceatannol.
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Piceatannol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Piceatannol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Styrenes / Resorcinols / Catechols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Catechol / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Phenol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
stilbenol (CHEBI:28814) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes, Stilbenes (C05901) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090006)
Affected organisms
Not Available

Chemical Identifiers

UNII
6KS3LS0D4F
CAS number
10083-24-6
InChI Key
CDRPUGZCRXZLFL-OWOJBTEDSA-N
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+
IUPAC Name
4-[(1E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
SMILES
OC1=CC(\C=C\C2=CC=C(O)C(O)=C2)=CC(O)=C1

References

Synthesis Reference

Alain Schouteeten, Sebastien Jus, Jean-Claude Vallejos, "Novel Process For The Synthesis Of (E)-Stilbene Derivatives Which Makes It Possible To Obtain Resveratrol And Piceatannol." U.S. Patent US20100004483, issued January 07, 2010.

US20100004483
General References
Not Available
Human Metabolome Database
HMDB0004215
KEGG Compound
C05901
PubChem Compound
667639
PubChem Substance
99444870
ChemSpider
581006
BindingDB
50045936
ChEBI
28814
ChEMBL
CHEMBL69863
ZINC
ZINC000000014036
PDBe Ligand
PIT
Wikipedia
Piceatannol
PDB Entries
2jj1 / 4hd8 / 5u97 / 7ccv / 8w43 / 8w48 / 8wrk

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Not Yet RecruitingTreatmentAcute Respiratory Distress Syndrome (ARDS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.097 mg/mLALOGPS
logP2.12ALOGPS
logP3.1Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.41Chemaxon
pKa (Strongest Basic)-6.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area80.92 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity69.44 m3·mol-1Chemaxon
Polarizability25.46 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9526
Blood Brain Barrier-0.5495
Caco-2 permeable+0.5789
P-glycoprotein substrateNon-substrate0.5669
P-glycoprotein inhibitor INon-inhibitor0.9237
P-glycoprotein inhibitor IINon-inhibitor0.9761
Renal organic cation transporterNon-inhibitor0.9072
CYP450 2C9 substrateNon-substrate0.7658
CYP450 2D6 substrateNon-substrate0.9068
CYP450 3A4 substrateNon-substrate0.6661
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.6182
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.5427
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7651
Ames testNon AMES toxic0.6502
CarcinogenicityNon-carcinogens0.8962
BiodegradationNot ready biodegradable0.7819
Rat acute toxicity1.8860 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9444
hERG inhibition (predictor II)Non-inhibitor0.8884
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-001i-1642190000-e16674c5bbe3fb0a7cb2
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-001i-1852290000-a6082a666145e38ac8c1
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-006x-0690000000-50e7f72f479a8b6f10a4
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-1642190000-e16674c5bbe3fb0a7cb2
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-1852290000-a6082a666145e38ac8c1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0190000000-a97faa170da01eb8120a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-13c17ef3f094265feb3c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00or-0590000000-f1f29ed911596bdf0ad5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-0390000000-45b601f23a97cb4a4553
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06vi-1920000000-f078edb257f0cd986381
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1900000000-3a8949ed7b1c58e2a9ee
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-166.2774361
predicted
DarkChem Lite v0.1.0
[M-H]-173.9081361
predicted
DarkChem Lite v0.1.0
[M-H]-165.6972361
predicted
DarkChem Lite v0.1.0
[M-H]-163.04889
predicted
DeepCCS 1.0 (2019)
[M+H]+169.5414361
predicted
DarkChem Lite v0.1.0
[M+H]+179.9121361
predicted
DarkChem Lite v0.1.0
[M+H]+167.6694361
predicted
DarkChem Lite v0.1.0
[M+H]+165.40689
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.6470361
predicted
DarkChem Lite v0.1.0
[M+Na]+175.0841361
predicted
DarkChem Lite v0.1.0
[M+Na]+165.2746361
predicted
DarkChem Lite v0.1.0
[M+Na]+171.50005
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. ATP synthase subunit alpha, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5A1
Uniprot ID
P25705
Uniprot Name
ATP synthase subunit alpha, mitochondrial
Molecular Weight
59750.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. ATP synthase subunit beta, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5B
Uniprot ID
P06576
Uniprot Name
ATP synthase subunit beta, mitochondrial
Molecular Weight
56559.42 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details3. ATP synthase subunit gamma, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5C1
Uniprot ID
P36542
Uniprot Name
ATP synthase subunit gamma, mitochondrial
Molecular Weight
32995.665 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52