3-{[(4-CARBOXY-2-HYDROXYANILINE]SULFONYL}THIOPHENE-2-CARBOXYLIC ACID

Identification

Name
3-{[(4-CARBOXY-2-HYDROXYANILINE]SULFONYL}THIOPHENE-2-CARBOXYLIC ACID
Accession Number
DB07927
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: 343.332
Monoisotopic: 342.982043027
Chemical Formula
C12H9NO7S2
InChI Key
RDPXXOOKKRIKFN-UHFFFAOYSA-N
InChI
InChI=1S/C12H9NO7S2/c14-8-5-6(11(15)16)1-2-7(8)13-22(19,20)9-3-4-21-10(9)12(17)18/h1-5,13-14H,(H,15,16)(H,17,18)
IUPAC Name
3-[(4-carboxy-2-hydroxyphenyl)sulfamoyl]thiophene-2-carboxylic acid
SMILES
OC(=O)C1=C(C=CS1)S(=O)(=O)NC1=C(O)C=C(C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot 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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
657106
PubChem Substance
99444398
ChemSpider
571308
BindingDB
50324682
ChEMBL
CHEMBL1222313
HET
HTC
PDB Entries
1xgj

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 Solubility0.187 mg/mLALOGPS
logP1.67ALOGPS
logP2.04ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.27 m3·mol-1ChemAxon
Polarizability30.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.897
Blood Brain Barrier-0.6431
Caco-2 permeable-0.6461
P-glycoprotein substrateNon-substrate0.84
P-glycoprotein inhibitor INon-inhibitor0.9493
P-glycoprotein inhibitor IINon-inhibitor0.963
Renal organic cation transporterNon-inhibitor0.9421
CYP450 2C9 substrateNon-substrate0.6009
CYP450 2D6 substrateNon-substrate0.8438
CYP450 3A4 substrateNon-substrate0.6962
CYP450 1A2 substrateNon-inhibitor0.6544
CYP450 2C9 inhibitorNon-inhibitor0.5346
CYP450 2D6 inhibitorNon-inhibitor0.9139
CYP450 2C19 inhibitorNon-inhibitor0.7245
CYP450 3A4 inhibitorNon-inhibitor0.8539
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8251
Ames testNon AMES toxic0.8147
CarcinogenicityNon-carcinogens0.7157
BiodegradationNot ready biodegradable0.8889
Rat acute toxicity2.0844 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9552
hERG inhibition (predictor II)Non-inhibitor0.8825
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 sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Sulfanilides
Direct Parent
Sulfanilides
Alternative Parents
Hydroxybenzoic acid derivatives / Benzoic acids / Thiophene carboxylic acids / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Organosulfonamides / Dicarboxylic acids and derivatives / Aminosulfonyl compounds / Heteroaromatic compounds
show 6 more
Substituents
Hydroxybenzoic acid / Sulfanilide / Benzoic acid or derivatives / Benzoic acid / Benzoyl / Thiophene carboxylic acid / Thiophene carboxylic acid or derivatives / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
Gene Name
ampC
Uniprot ID
P00811
Uniprot Name
Beta-lactamase
Molecular Weight
41555.3 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 15:27 / Updated on December 01, 2017 15:57