Identification

Name
Myricetin
Accession Number
DB02375  (EXPT02265)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 3,3',4,4',5',7-Hexahydro-2-phenyl-4H-chromen-4-one
  • 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
  • 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
  • 3,5,7,3',4',5'-Hexahydroxyflavone
  • Cannabiscetin
  • MYC
  • Myricetol
  • Myricitin
External IDs
NSC-407290
Categories
UNII
76XC01FTOJ
CAS number
529-44-2
Weight
Average: 318.2351
Monoisotopic: 318.037567296
Chemical Formula
C15H10O8
InChI Key
IKMDFBPHZNJCSN-UHFFFAOYSA-N
InChI
InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
IUPAC Name
3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
SMILES
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformNot AvailableHuman
UTyrosine-protein kinase JAK1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB02755
KEGG Compound
C10107
PubChem Compound
5281672
PubChem Substance
46508126
ChemSpider
4444991
BindingDB
15236
ChEBI
18152
ChEMBL
CHEMBL164
HET
MYC
PDB Entries
1e90 / 2iod / 2o63 / 3c1t / 3hbf / 4gqr / 5hxc

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)357 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.301 mg/mLALOGPS
logP1.66ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.84 m3·mol-1ChemAxon
Polarizability29.47 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.965
Blood Brain Barrier-0.5711
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5629
P-glycoprotein inhibitor INon-inhibitor0.9297
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.931
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.653
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.5823
CYP450 2D6 inhibitorNon-inhibitor0.9287
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.6951
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5822
Ames testNon AMES toxic0.722
CarcinogenicityNon-carcinogens0.945
BiodegradationNot ready biodegradable0.8672
Rat acute toxicity3.0200 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.8161
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000t-0943100000-fa00c6f71be0c6675599
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-005c-2954350000-46c24c9458aadfd2a711
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000t-0943100000-fa00c6f71be0c6675599
GC-MS Spectrum - GC-MSGC-MSsplash10-005c-2954350000-46c24c9458aadfd2a711
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, PositiveLC-MS/MSsplash10-014i-0009000000-99c784d42ece911ecc13
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-014i-0907000000-0b4ff7a72a459baa829c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0pbi-0900000000-b492f594bdca4c8132a0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0uxr-0950000000-55c90a0d932630c6d644
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-014i-0329000000-43069a5bf007fae18a27
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , PositiveLC-MS/MSsplash10-014i-0009000000-2b98dfcc4f869be90285
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-014i-0009104000-6dada42248181a0149f3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-9a84f52c6a2f1aaec1a7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0219000000-36b340f32ee87232a4d1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0v0a-5931000000-56b06c0109d323a15bc9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-7c52125f5ee8fbc51ba0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0229000000-413e7e87d4aaf205ca23
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-066u-5930000000-ebd17a876ef4c64d13c0
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0009000000-7494718b3a96d5664b53
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0209000000-2b4763ddb9eb888c9bfd
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0v09-0901000000-6861fe274e8b0b6b663e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udr-0900000000-e982d07ed9f6838c4ee0
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-052r-0900000000-474334cb2aaeb44eea07
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0907000000-0b4ff7a72a459baa829c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0pbi-0900000000-b492f594bdca4c8132a0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0900000000-c3c0a09ce51bc30450a3
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0901000000-cc55004a9b0c91bf5eaa
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0329000000-145af0cf36801876d9b7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0109000000-5d7b59045aa049855cdd
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0009022000-33314f5bfa07257330d7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0017494000-e120a5efd3ab8ebbed33
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-016r-0809000000-4de3f39410ede65940bb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-016r-0918000000-701d6150f84e94ae3d54
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0009000000-35024ff951cd0ca242e4
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014r-0079000000-b798a1be942ffa6396d2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-6382ca3e22fab99bb5c5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-2be130655db7b1836443
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0329000000-ae42217b3eeed91bf007
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uxr-0971000000-1c81de772076fa4b3639
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0940000000-0b29721220164d18a890
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uxr-0950000000-55c90a0d932630c6d644
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0329000000-43069a5bf007fae18a27
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0fk9-0491000000-927fcd293091811014c9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0fk9-0491000000-92d89477c3c4a044f0a0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0fk9-0491000000-d2dd2474c48b2ecfd653
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0fk9-0491000000-6ab1e59b0d1e492965fc
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0gb9-2951000000-55186f59f5d6ec659c2d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-1947000000-657f4be0c2fc77929b60
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavones
Direct Parent
Flavonols
Alternative Parents
3'-hydroxyflavonoids / 3-hydroxyflavonoids / 4'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Chromones / Pyrogallols and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Pyranones and derivatives / 1-hydroxy-4-unsubstituted benzenoids
show 7 more
Substituents
3-hydroxyflavone / 3'-hydroxyflavonoid / 3-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Hydroxyflavonoid / Chromone / Benzopyran / 1-benzopyran
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
7-hydroxyflavonol, hexahydroxyflavone (CHEBI:18152) / flavonols, Flavones and Flavonols (C10107) / Flavones and Flavonols (LMPK12110001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recr...
Gene Name
PIK3CG
Uniprot ID
P48736
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
Molecular Weight
126452.625 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Tyrosine kinase of the non-receptor type, involved in the IFN-alpha/beta/gamma signal pathway. Kinase partner for the interleukin (IL)-2 receptor.
Gene Name
JAK1
Uniprot ID
P23458
Uniprot Name
Tyrosine-protein kinase JAK1
Molecular Weight
133275.995 Da
References
  1. Kumamoto T, Fujii M, Hou DX: Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett. 2009 Mar 8;275(1):17-26. doi: 10.1016/j.canlet.2008.09.027. Epub 2008 Nov 7. [PubMed:18995957]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. [PubMed:11306701]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:13