[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid

Identification

Name
[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid
Accession Number
DB08098
Type
Small Molecule
Groups
Experimental
Description

{[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid is a solid. This compound belongs to the nitrofurans. These are compounds containing a furan ring which bears a nitro group. {[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid targets the protein aldose reductase.

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 271.207
Monoisotopic: 270.989905597
Chemical Formula
C8H5N3O6S
InChI Key
ITBNJCVIFHSKRL-UHFFFAOYSA-N
InChI
InChI=1S/C8H5N3O6S/c12-6(13)3-18-8-10-9-7(17-8)4-1-2-5(16-4)11(14)15/h1-2H,3H2,(H,12,13)
IUPAC Name
2-{[5-(5-nitrofuran-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetic acid
SMILES
OC(=O)CSC1=NN=C(O1)C1=CC=C(O1)[N+]([O-])=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductaseNot AvailableHuman
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
Not Available
External Links
PubChem Compound
2817424
PubChem Substance
99444569
ChemSpider
2095728
BindingDB
16235
ChEBI
43741
HET
LIT
PDB Entries
2ikh

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 Solubility0.171 mg/mLALOGPS
logP0.66ALOGPS
logP0.55ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area135.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.52 m3·mol-1ChemAxon
Polarizability22.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8131
Blood Brain Barrier+0.7737
Caco-2 permeable-0.5829
P-glycoprotein substrateNon-substrate0.928
P-glycoprotein inhibitor INon-inhibitor0.8861
P-glycoprotein inhibitor IINon-inhibitor0.8667
Renal organic cation transporterNon-inhibitor0.9592
CYP450 2C9 substrateNon-substrate0.8216
CYP450 2D6 substrateNon-substrate0.8255
CYP450 3A4 substrateNon-substrate0.5349
CYP450 1A2 substrateInhibitor0.5096
CYP450 2C9 inhibitorNon-inhibitor0.6453
CYP450 2D6 inhibitorNon-inhibitor0.9024
CYP450 2C19 inhibitorNon-inhibitor0.5348
CYP450 3A4 inhibitorNon-inhibitor0.865
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5911
Ames testAMES toxic0.8191
CarcinogenicityNon-carcinogens0.6633
BiodegradationNot ready biodegradable0.6927
Rat acute toxicity2.5819 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.992
hERG inhibition (predictor II)Non-inhibitor0.9296
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 nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furans
Sub Class
Nitrofurans
Direct Parent
Nitrofurans
Alternative Parents
Nitroaromatic compounds / Alkylarylthioethers / 1,3,4-oxadiazoles / Heteroaromatic compounds / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboxylic acids / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 7 more
Substituents
2-nitrofuran / Aryl thioether / Nitroaromatic compound / Alkylarylthioether / 1,3,4-oxadiazole / Azole / Oxadiazole / Heteroaromatic compound / C-nitro compound / Organic nitro compound
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
C-nitro compound, furans, 1,3,4-oxadiazole (CHEBI:43741)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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 15:28 / Updated on December 01, 2017 16:00