(5Z)-3-(4-CHLOROPHENYL)-4-HYDROXY-5-(1-NAPHTHYLMETHYLENE)FURAN-2(5H)-ONE

Identification

Name
(5Z)-3-(4-CHLOROPHENYL)-4-HYDROXY-5-(1-NAPHTHYLMETHYLENE)FURAN-2(5H)-ONE
Accession Number
DB07296
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 348.779
Monoisotopic: 348.055321989
Chemical Formula
C21H13ClO3
InChI Key
PLGHLEBIWUQEPR-PDGQHHTCSA-N
InChI
InChI=1S/C21H13ClO3/c22-16-10-8-14(9-11-16)19-20(23)18(25-21(19)24)12-15-6-3-5-13-4-1-2-7-17(13)15/h1-12,23H/b18-12-
IUPAC Name
(5Z)-3-(4-chlorophenyl)-4-hydroxy-5-(naphthalen-1-ylmethylidene)-2,5-dihydrofuran-2-one
SMILES
OC1=C(C(=O)O\C1=C/C1=CC=CC2=CC=CC=C12)C1=CC=C(Cl)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-N-acetylenolpyruvoylglucosamine reductaseNot AvailableEscherichia coli (strain K12)
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
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

References

General References
Not Available
External Links
PubChem Compound
54682555
PubChem Substance
99443767
ChemSpider
22376418
ChEMBL
CHEMBL197865
ZINC
ZINC000028565517
PDBe Ligand
973
PDB Entries
2q85

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 Solubility0.000348 mg/mLALOGPS
logP5.23ALOGPS
logP4.95ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)6.76ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.38 m3·mol-1ChemAxon
Polarizability36.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8493
Caco-2 permeable+0.5898
P-glycoprotein substrateNon-substrate0.6274
P-glycoprotein inhibitor INon-inhibitor0.668
P-glycoprotein inhibitor IINon-inhibitor0.812
Renal organic cation transporterNon-inhibitor0.852
CYP450 2C9 substrateNon-substrate0.7952
CYP450 2D6 substrateNon-substrate0.8998
CYP450 3A4 substrateNon-substrate0.6129
CYP450 1A2 substrateNon-inhibitor0.6084
CYP450 2C9 inhibitorNon-inhibitor0.5627
CYP450 2D6 inhibitorNon-inhibitor0.864
CYP450 2C19 inhibitorNon-inhibitor0.6841
CYP450 3A4 inhibitorNon-inhibitor0.7876
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6568
Ames testNon AMES toxic0.646
CarcinogenicityNon-carcinogens0.8847
BiodegradationNot ready biodegradable0.9911
Rat acute toxicity2.7907 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9554
hERG inhibition (predictor II)Non-inhibitor0.9015
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 naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Chlorobenzenes / Butenolides / Aryl chlorides / Vinylogous acids / Enol esters / Enoate esters / Lactones / Oxacyclic compounds / Monocarboxylic acids and derivatives / Enols
show 4 more
Substituents
Naphthalene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / 2-furanone / Vinylogous acid / Alpha,beta-unsaturated carboxylic ester / Enoate ester
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
butenolide, monochlorobenzenes, naphthalenes (CHEBI:47186)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramate dehydrogenase activity
Specific Function
Cell wall formation.
Gene Name
murB
Uniprot ID
P08373
Uniprot Name
UDP-N-acetylenolpyruvoylglucosamine reductase
Molecular Weight
37850.835 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:20 / Updated on June 12, 2020 10:52

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