Identification
- Generic Name
- Sofalcone
- DrugBank Accession Number
- DB05197
- Background
Sofalcone is a mucosal protective agent that has been reported to inhibit growth of Helicobacter pylori. on adherence, production of vacuolating toxin (VT), and induction of interleukin-8 (IL-8) secretion by H. pylori.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Sofalcone (DB05197)
- Weight
- Average: 450.5235
Monoisotopic: 450.204238692 - Chemical Formula
- C27H30O6
- Synonyms
- Sofalcone
Pharmacology
- Indication
Investigated for use/treatment in gastroenteritis and ulcers.
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
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Sofalcone has been reported to have an anti-bacterial effect on H. pylori and the inhibitory effects against the pathogenic factor of H. pylori in addition to the mucosal protective effect due to the inhibition of prostaglandins degradation enzyme. Sofalcone has a direct bactericidal effect on H pylori, anti-urease activity and reduces the adhesion of this organism to gastric epithelial cells
- 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.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 linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Linear 1,3-diarylpropanoids
- Sub Class
- Not Available
- Direct Parent
- Linear 1,3-diarylpropanoids
- Alternative Parents
- Phenoxyacetic acid derivatives / Styrenes / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Aryl ketones / Alkyl aryl ethers / Enones / Acryloyl compounds / Monocarboxylic acids and derivatives show 3 more
- Substituents
- Acryloyl-group / Alkyl aryl ether / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl ketone / Benzenoid / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative show 14 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2B668TJX8E
- CAS number
- 64506-49-6
- InChI Key
- GFWRVVCDTLRWPK-KPKJPENVSA-N
- InChI
- InChI=1S/C27H30O6/c1-19(2)13-15-31-22-8-5-21(6-9-22)7-12-25(28)24-11-10-23(32-16-14-20(3)4)17-26(24)33-18-27(29)30/h5-14,17H,15-16,18H2,1-4H3,(H,29,30)/b12-7+
- IUPAC Name
- 2-{5-[(3-methylbut-2-en-1-yl)oxy]-2-[(2E)-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-enoyl]phenoxy}acetic acid
- SMILES
- CC(C)=CCOC1=CC=C(\C=C\C(=O)C2=C(OCC(O)=O)C=C(OCC=C(C)C)C=C2)C=C1
References
- General References
- Isomoto H, Furusu H, Ohnita K, Wen CY, Inoue K, Kohno S: Sofalcone, a mucoprotective agent, increases the cure rate of Helicobacter pylori infection when combined with rabeprazole, amoxicillin and clarithromycin. World J Gastroenterol. 2005 Mar 21;11(11):1629-33. [Article]
- External Links
- Human Metabolome Database
- HMDB0042013
- PubChem Compound
- 5282219
- PubChem Substance
- 175426956
- ChemSpider
- 4445402
- ChEMBL
- CHEMBL1441961
- ZINC
- ZINC000003831462
- Wikipedia
- Sofalcone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000674 mg/mL ALOGPS logP 4.94 ALOGPS logP 5.62 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) 3.22 Chemaxon pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 82.06 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 130.59 m3·mol-1 Chemaxon Polarizability 51.22 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9526 Blood Brain Barrier - 0.6773 Caco-2 permeable + 0.5992 P-glycoprotein substrate Substrate 0.7059 P-glycoprotein inhibitor I Inhibitor 0.8371 P-glycoprotein inhibitor II Non-inhibitor 0.5324 Renal organic cation transporter Non-inhibitor 0.8337 CYP450 2C9 substrate Non-substrate 0.7915 CYP450 2D6 substrate Non-substrate 0.8764 CYP450 3A4 substrate Substrate 0.576 CYP450 1A2 substrate Inhibitor 0.6782 CYP450 2C9 inhibitor Inhibitor 0.6229 CYP450 2D6 inhibitor Non-inhibitor 0.6369 CYP450 2C19 inhibitor Inhibitor 0.6804 CYP450 3A4 inhibitor Non-inhibitor 0.8962 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7038 Ames test Non AMES toxic 0.7519 Carcinogenicity Non-carcinogens 0.8314 Biodegradation Not ready biodegradable 0.6783 Rat acute toxicity 1.6850 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9577 hERG inhibition (predictor II) Non-inhibitor 0.8679
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Prostaglandin-e2 9-reductase activity
- Specific Function
- NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. ...
- Gene Name
- CBR1
- Uniprot ID
- P16152
- Uniprot Name
- Carbonyl reductase [NADPH] 1
- Molecular Weight
- 30374.73 Da
References
- Kobayashi K, Higuchi K, Arakawa T, Matsumoto T, Nagura H: Effect of sofalcone on localization of 15-hydroxyprostaglandin dehydrogenase, an enzyme that metabolizes prostaglandin E2, in rat gastric mucosa: an immunohistochemical study. J Clin Gastroenterol. 1992;14 Suppl 1:S39-42. [Article]
Drug created at October 21, 2007 22:24 / Updated at February 21, 2021 18:51