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
- Epicatechin
- DrugBank Accession Number
- DB12039
- Background
Epicatechin has been used in trials studying the treatment of Pre-diabetes.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Epicatechin (DB12039)
- Weight
- Average: 290.2681
Monoisotopic: 290.07903818 - Chemical Formula
- C15H14O6
- Synonyms
- Not Available
- External IDs
- NSC-81161
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans - 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
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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as catechins. These are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Flavans
- Direct Parent
- Catechins
- Alternative Parents
- 7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / 3-hydroxyflavonoids / 3'-hydroxyflavonoids / 1-benzopyrans / Catechols / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids show 5 more
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 3-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alcohol / Alkyl aryl ether show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- polyphenol, catechin (CHEBI:90) / Flavans, Flavanols and Leucoanthocyanidins, Flavan 3-ols, Condensed tannins (Proanthocyanidins) (C09727) / Flavans, Flavanols and Leucoanthocyanidins (LMPK12020003)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 34PHS7TU43
- CAS number
- 490-46-0
- InChI Key
- PFTAWBLQPZVEMU-UKRRQHHQSA-N
- InChI
- InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
- IUPAC Name
- (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
- SMILES
- O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001871
- KEGG Compound
- C09727
- PubChem Compound
- 72276
- PubChem Substance
- 347828350
- ChemSpider
- 65230
- BindingDB
- 23417
- 2641822
- ChEBI
- 90
- ChEMBL
- CHEMBL583912
- ZINC
- ZINC000000119988
- PDBe Ligand
- 28E
- Wikipedia
- Catechin
- PDB Entries
- 4ma6 / 6awt / 6awv / 6ax0
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 data2 Completed Treatment Becker's Muscular Dystrophy (BMD) 1 somestatus stop reason just information to hide 1 Completed Treatment Impaired Glucose Tolerance 2 somestatus stop reason just information to hide 1 Withdrawn Treatment Pulmonary Arterial Hypertension (PAH) 1 somestatus stop reason just information to hide 1, 2 Completed Treatment Becker's Muscular Dystrophy (BMD) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.645 mg/mL ALOGPS logP 1.02 ALOGPS logP 1.8 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 9 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 110.38 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 74 m3·mol-1 Chemaxon Polarizability 28.13 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]- 181.1549343 predictedDarkChem Lite v0.1.0 [M-H]- 180.4741343 predictedDarkChem Lite v0.1.0 [M-H]- 180.3276343 predictedDarkChem Lite v0.1.0 [M-H]- 167.56252 predictedDeepCCS 1.0 (2019) [M+H]+ 182.0929343 predictedDarkChem Lite v0.1.0 [M+H]+ 182.0571343 predictedDarkChem Lite v0.1.0 [M+H]+ 181.9812343 predictedDarkChem Lite v0.1.0 [M+H]+ 169.92052 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.3759343 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.4571343 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.8676343 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.57817 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- Heme binding
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 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 October 20, 2016 21:14 / Updated at August 27, 2024 19:15