Diosmetin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Diosmetin
Accession Number
DB11259
Type
Small Molecule
Groups
Experimental
Description

Diosmetin is an O-methylated flavone and the aglycone part of the flavonoid glycosides diosmin that occurs naturally in citrus fruits [2]. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflamatory activities [2]. It also acts as a weak TrkB receptor agonist [1].

Structure
Thumb
Synonyms
  • 3',5,7-trihydroxy-4'-methoxyflavone
  • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
  • Luteolin 4'-methyl ether
  • Salinigricoflavonol
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gingjinhyang Seol WhiteningLotion0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-082011-06-01Us
Gongjinhyang Seol WhiteningCream0.10 g/100gTopicalLg Household & Health Care Ltd.2010-03-24Not applicableUs
Gongjinhyang Seol Whitening EssenceCream0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-03-262011-06-01Us
Isa Knox Wxii Plus Whitening Revolution SerumCream0.11 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-23Not applicableUs
Isaknox X202 Whitening Secret EssenceCream0.055 mL/100mLTopicalLg Household & Health Care Ltd.2011-06-01Not applicableUs
Whoo Gongjinhyang Seol Whitening Jin EssenceCream0.055 mL/100mLTopicalLg Household & Health Care Ltd.2010-05-24Not applicableUs
Categories
UNII
TWZ37241OT
CAS number
520-34-3
Weight
Average: 300.2629
Monoisotopic: 300.063388116
Chemical Formula
C16H12O6
InChI Key
MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
IUPAC Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption

Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body [2].

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
  1. Jang SW, Liu X, Yepes M, Shepherd KR, Miller GW, Liu Y, Wilson WD, Xiao G, Blanchi B, Sun YE, Ye K: A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone. Proc Natl Acad Sci U S A. 2010 Feb 9;107(6):2687-92. doi: 10.1073/pnas.0913572107. Epub 2010 Jan 25. [PubMed:20133810]
  2. Patel K, Gadewar M, Tahilyani V, Patel DK: A review on pharmacological and analytical aspects of diosmetin: a concise report. Chin J Integr Med. 2013 Oct;19(10):792-800. doi: 10.1007/s11655-013-1595-3. Epub 2013 Oct 4. [PubMed:24092244]
External Links
Human Metabolome Database
HMDB0029676
KEGG Compound
C10038
PubChem Compound
5281612
PubChem Substance
347827956
ChemSpider
4444931
BindingDB
23414
ChEBI
4630
ChEMBL
CHEMBL90568
Wikipedia
Diosmetin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LotionTopical0.1 mL/100mL
CreamTopical0.10 g/100g
CreamTopical0.1 mL/100mL
CreamTopical0.11 mL/100mL
CreamTopical0.055 mL/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0754 mg/mLALOGPS
logP3.06ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.38 m3·mol-1ChemAxon
Polarizability29.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-a4a0986393c64d566f91
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-9488c8767caac5f6b9b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-2590000000-e4455d0da36912d7b96a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-91f51b4b036d4731f305
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-b6f4a2a03e7355f95b1c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-0390000000-e296a45296f81b0f1454
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-001i-0090000000-ae5188debe4910fab9c6
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0090000000-6e1198f4157cda4df0ac
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0090000000-b23157e3c53d703e88d1
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-675379707ad9e98244a9
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0190000000-77edda567cd76512c52d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0094000000-0b3f48256d5c0ee7fb1b

Taxonomy

Description
This compound belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
O-methylated flavonoids
Direct Parent
4'-O-methylated flavonoids
Alternative Parents
3'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Flavones / Chromones / Methoxyphenols / Phenoxy compounds / Methoxybenzenes / Anisoles / 1-hydroxy-2-unsubstituted benzenoids
show 8 more
Substituents
4p-methoxyflavonoid-skeleton / 3'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Flavone / Hydroxyflavonoid / Chromone / Benzopyran / Methoxyphenol / 1-benzopyran
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monomethoxyflavone, trihydroxyflavone, 3'-hydroxyflavonoid (CHEBI:4630) / flavones, Flavones and Flavonols (C10038) / Flavones and Flavonols (LMPK12110824)

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 07:08