Sofalcone

Identification

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Name
Sofalcone
Accession Number
DB05197
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
2B668TJX8E
CAS number
64506-49-6
Weight
Average: 450.5235
Monoisotopic: 450.204238692
Chemical Formula
C27H30O6
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

Pharmacology

Indication

Investigated for use/treatment in gastroenteritis and ulcers.

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
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. 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. [PubMed:15786539]
External Links
Human Metabolome Database
HMDB0042013
PubChem Compound
5282219
PubChem Substance
175426956
ChemSpider
4445402
ChEMBL
CHEMBL1441961
Wikipedia
Sofalcone

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.000674 mg/mLALOGPS
logP4.94ALOGPS
logP5.62ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.59 m3·mol-1ChemAxon
Polarizability51.22 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9526
Blood Brain Barrier-0.6773
Caco-2 permeable+0.5992
P-glycoprotein substrateSubstrate0.7059
P-glycoprotein inhibitor IInhibitor0.8371
P-glycoprotein inhibitor IINon-inhibitor0.5324
Renal organic cation transporterNon-inhibitor0.8337
CYP450 2C9 substrateNon-substrate0.7915
CYP450 2D6 substrateNon-substrate0.8764
CYP450 3A4 substrateSubstrate0.576
CYP450 1A2 substrateInhibitor0.6782
CYP450 2C9 inhibitorInhibitor0.6229
CYP450 2D6 inhibitorNon-inhibitor0.6369
CYP450 2C19 inhibitorInhibitor0.6804
CYP450 3A4 inhibitorNon-inhibitor0.8962
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7038
Ames testNon AMES toxic0.7519
CarcinogenicityNon-carcinogens0.8314
BiodegradationNot ready biodegradable0.6783
Rat acute toxicity1.6850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9577
hERG inhibition (predictor II)Non-inhibitor0.8679
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Linear 1,3-diarylpropanoid / Phenoxyacetate / Phenoxy compound / Aryl ketone / Styrene / Phenol ether / Benzoyl / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
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
  1. 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. [PubMed:1629577]

Drug created on October 21, 2007 16:24 / Updated on June 04, 2019 06:15