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

Identification

Generic Name
Diosmetin
DrugBank Accession Number
DB11259
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 300.2629
Monoisotopic: 300.063388116
Chemical Formula
C16H12O6
Synonyms
  • 3',5,7-trihydroxy-4'-methoxyflavone
  • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
  • Luteolin 4'-methyl ether
  • Salinigricoflavonol

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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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.
Not Available
Food Interactions
Not Available

Products

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gingjinhyang Seol WhiteningLotion0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-082011-06-01US flag
Gongjinhyang Seol WhiteningCream0.10 g/100gTopicalLg Household & Health Care Ltd.2010-03-24Not applicableUS flag
Gongjinhyang Seol Whitening EssenceCream0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-03-262011-06-01US flag
Isa Knox Wxii Plus Whitening Revolution SerumCream0.11 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-23Not applicableUS flag
Isaknox X202 Whitening Secret EssenceCream0.055 mL/100mLTopicalLg Household & Health Care Ltd.2011-06-01Not applicableUS flag
Whoo Gongjinhyang Seol Whitening Jin EssenceCream0.055 mL/100mLTopicalLg Household & Health Care Ltd.2010-05-24Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Gingjinhyang Seol WhiteningDiosmetin (0.1 mL/100mL)LotionTopicalLg Household & Health Care Ltd.2010-04-082011-06-01US flag
Gongjinhyang Seol Whitening EssenceDiosmetin (0.1 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-03-262011-06-01US flag
Isaknox X202 Whitening Secret EssenceDiosmetin (0.055 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-06-01Not applicableUS flag
Whoo Gongjinhyang Seol Whitening Jin EssenceDiosmetin (0.055 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-05-24Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4p-methoxyflavonoid-skeleton / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound
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)
Affected organisms
Not Available

Chemical Identifiers

UNII
TWZ37241OT
CAS number
520-34-3
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

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0029676
KEGG Compound
C10038
PubChem Compound
5281612
PubChem Substance
347827956
ChemSpider
4444931
BindingDB
23414
RxNav
1314347
ChEBI
4630
ChEMBL
CHEMBL90568
ZINC
ZINC000005733652
PDBe Ligand
J8D
Wikipedia
Diosmetin
PDB Entries
6m8d

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Drug created at December 03, 2015 16:51 / Updated at June 12, 2020 16:53