NAV

3-[(4-Carboxy-2-hydroxyphenyl)sulfamoyl]-2-thiophenecarboxylic acid

Identification

Generic Name
3-[(4-Carboxy-2-hydroxyphenyl)sulfamoyl]-2-thiophenecarboxylic acid
DrugBank Accession Number
DB07927
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 343.332
Monoisotopic: 342.982043027
Chemical Formula
C12H9NO7S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

Adverse Effects
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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
Not Available
Chemical TaxonomyProvided by Classyfire
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
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
657106
PubChem Substance
99444398
ChemSpider
571308
BindingDB
50324682
ChEMBL
CHEMBL1222313
ZINC
ZINC000003881294
PDBe Ligand
HTC
PDB Entries
1xgj

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-0udi-2911000000-640fc1e62c5895504dd3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mo-0039000000-9efeab00fccf453a04d0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-b0800cf927f5749e2e61
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ou-0539000000-38c0f319e2f7ba93b429
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-1503c9c3e0f38a9c93a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fv-1940000000-b3c0c9d52f55a6e4a990
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05n1-2940000000-d61c9f739942f6c25fc1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.32553
predicted
DeepCCS 1.0 (2019)
[M+H]+171.68352
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.05281
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase
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. [Article]

Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52