Diosmetin
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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
- 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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ACytochrome P450 1B1 inhibitorHumans ASignal transducer and activator of transcription 3 inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gingjinhyang Seol Whitening Lotion 0.1 mL/100mL Topical Lg Household & Health Care Ltd. 2010-04-08 2011-06-01 US Gongjinhyang Seol Whitening Cream 0.10 g/100g Topical Lg Household & Health Care Ltd. 2010-03-24 Not applicable US Gongjinhyang Seol Whitening Essence Cream 0.1 mL/100mL Topical Lg Household & Health Care Ltd. 2010-03-26 2011-06-01 US Isa Knox Wxii Plus Whitening Revolution Serum Cream 0.11 mL/100mL Topical Lg Household & Health Care Ltd. 2010-04-23 Not applicable US Isaknox X202 Whitening Secret Essence Cream 0.055 mL/100mL Topical Lg Household & Health Care Ltd. 2011-06-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Gingjinhyang Seol Whitening Diosmetin (0.1 mL/100mL) Lotion Topical Lg Household & Health Care Ltd. 2010-04-08 2011-06-01 US Gongjinhyang Seol Whitening Essence Diosmetin (0.1 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-03-26 2011-06-01 US Isaknox X202 Whitening Secret Essence Diosmetin (0.055 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2011-06-01 Not applicable US Whoo Gongjinhyang Seol Whitening Jin Essence Diosmetin (0.055 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-05-24 Not applicable US
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
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0029676
- KEGG Compound
- C10038
- PubChem Compound
- 5281612
- PubChem Substance
- 347827956
- ChemSpider
- 4444931
- BindingDB
- 23414
- 1314347
- ChEBI
- 4630
- ChEMBL
- CHEMBL90568
- ZINC
- ZINC000005733652
- PDBe Ligand
- J8D
- Wikipedia
- Diosmetin
- PDB Entries
- 6m8d
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lotion Topical 0.1 mL/100mL Cream Topical 0.10 g/100g Cream Topical 0.1 mL/100mL Cream Topical 0.11 mL/100mL Cream Topical 0.055 mL/100mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0754 mg/mL ALOGPS logP 3.06 ALOGPS logP 2.55 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 6.58 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 96.22 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 79.38 m3·mol-1 Chemaxon Polarizability 29.84 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.3338886 predictedDarkChem Lite v0.1.0 [M-H]- 183.3531886 predictedDarkChem Lite v0.1.0 [M-H]- 183.4594886 predictedDarkChem Lite v0.1.0 [M-H]- 169.99042 predictedDeepCCS 1.0 (2019) [M+H]+ 186.1046886 predictedDarkChem Lite v0.1.0 [M+H]+ 186.9491886 predictedDarkChem Lite v0.1.0 [M+H]+ 187.4137886 predictedDarkChem Lite v0.1.0 [M+H]+ 172.34842 predictedDeepCCS 1.0 (2019) [M+Na]+ 184.0612886 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.9671886 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.7953886 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.85918 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsCytochrome P450 1B1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)
- Specific Function
- aromatase activity
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Signal transducer and transcription activator that mediates cellular responses to interleukins, KITLG/SCF, LEP and other growth factors (PubMed:10688651, PubMed:12359225, PubMed:12873986, PubMed:15194700, PubMed:15653507, PubMed:16285960, PubMed:17344214, PubMed:18242580, PubMed:18782771, PubMed:22306293, PubMed:23084476, PubMed:28262505, PubMed:32929201). Once activated, recruits coactivators, such as NCOA1 or MED1, to the promoter region of the target gene (PubMed:15653507, PubMed:16285960, PubMed:17344214, PubMed:18782771, PubMed:28262505, PubMed:32929201). May mediate cellular responses to activated FGFR1, FGFR2, FGFR3 and FGFR4 (PubMed:12873986). Upon activation of IL6ST/gp130 signaling by interleukin-6 (IL6), binds to the IL6-responsive elements identified in the promoters of various acute-phase protein genes (PubMed:12359225). Activated by IL31 through IL31RA (PubMed:15194700). Acts as a regulator of inflammatory response by regulating differentiation of naive CD4(+) T-cells into T-helper Th17 or regulatory T-cells (Treg): acetylation promotes its transcription activity and cell differentiation while deacetylation and oxidation of lysine residues by LOXL3 inhibits differentiation (PubMed:28065600, PubMed:28262505). Involved in cell cycle regulation by inducing the expression of key genes for the progression from G1 to S phase, such as CCND1 (PubMed:17344214). Mediates the effects of LEP on melanocortin production, body energy homeostasis and lactation (By similarity). May play an apoptotic role by transctivating BIRC5 expression under LEP activation (PubMed:18242580). Cytoplasmic STAT3 represses macroautophagy by inhibiting EIF2AK2/PKR activity (PubMed:23084476). Plays a crucial role in basal beta cell functions, such as regulation of insulin secretion (By similarity). Following JAK/STAT signaling activation and as part of a complex with NFATC3 and NFATC4, binds to the alpha-beta E4 promoter region of CRYAB and activates transcription in cardiomyocytes (By similarity)
- Specific Function
- chromatin DNA binding
- Gene Name
- STAT3
- Uniprot ID
- P40763
- Uniprot Name
- Signal transducer and activator of transcription 3
- Molecular Weight
- 88067.215 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at December 03, 2015 16:51 / Updated at August 26, 2024 19:22