(1R)-1-(2-THIENYLACETYLAMINO)-1-(3-CARBOXYPHENYL)METHYLBORONIC ACID

Identification

Name
(1R)-1-(2-THIENYLACETYLAMINO)-1-(3-CARBOXYPHENYL)METHYLBORONIC ACID
Accession Number
DB08551
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: 319.141
Monoisotopic: 319.068573719
Chemical Formula
C14H14BNO5S
InChI Key
HQLQTGGLHBYZSA-ZDUSSCGKSA-N
InChI
InChI=1S/C14H14BNO5S/c17-12(8-11-5-2-6-22-11)16-13(15(20)21)9-3-1-4-10(7-9)14(18)19/h1-7,13,20-21H,8H2,(H,16,17)(H,18,19)/t13-/m0/s1
IUPAC Name
3-[(R)-(dihydroxyboranyl)[2-(thiophen-2-yl)acetamido]methyl]benzoic acid
SMILES
[H][[email protected]@](NC(=O)CC1=CC=CS1)(B(O)O)C1=CC(=CC=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)
UBeta-lactamase TEMNot AvailableEscherichia coli
UBeta-lactamaseNot AvailableEscherichia coli
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
5289377
PubChem Substance
99445022
ChemSpider
4451363
ChEMBL
CHEMBL257468
HET
SM2
PDB Entries
1mxo / 1nxy / 1pi5 / 1ym1 / 5chj / 5w13

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 Solubility0.0297 mg/mLALOGPS
logP1.22ALOGPS
logP2.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.53 m3·mol-1ChemAxon
Polarizability31.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7856
Blood Brain Barrier+0.8401
Caco-2 permeable-0.6479
P-glycoprotein substrateNon-substrate0.7329
P-glycoprotein inhibitor INon-inhibitor0.9815
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9516
CYP450 2C9 substrateNon-substrate0.5504
CYP450 2D6 substrateNon-substrate0.8056
CYP450 3A4 substrateNon-substrate0.6792
CYP450 1A2 substrateNon-inhibitor0.8291
CYP450 2C9 inhibitorNon-inhibitor0.8476
CYP450 2D6 inhibitorNon-inhibitor0.9244
CYP450 2C19 inhibitorNon-inhibitor0.8409
CYP450 3A4 inhibitorNon-inhibitor0.9402
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9363
Ames testNon AMES toxic0.746
CarcinogenicityNon-carcinogens0.8417
BiodegradationReady biodegradable0.5224
Rat acute toxicity2.2065 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9944
hERG inhibition (predictor II)Non-inhibitor0.9607
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 benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acids
Alternative Parents
Benzoyl derivatives / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Boronic acids / Organic metalloid salts / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Benzoic acid / Benzoyl / Thiophene / Heteroaromatic compound / Boronic acid derivative / Boronic acid / Carboxamide group / Secondary carboxylic acid amide / Organic metalloid salt / Organoheterocyclic compound
show 16 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]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins. TEM-3 and TEM-4 are capable of hydrolyzing cefotaxime and ceftazidime. TEM-5 is capable of hydrolyzing ceftazidime. TEM-6 is capable of hydrolyzing ceftazidime and aztreonam. TEM-8/CAZ-2, TEM-16/CAZ-7 and TEM-24/CAZ-6 are markedly active against ceftazidime. IRT-4 shows resistance to beta-lactamase inhibitors.
Specific Function
Beta-lactamase activity
Gene Name
bla
Uniprot ID
P62593
Uniprot Name
Beta-lactamase TEM
Molecular Weight
31514.865 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]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
Not Available
Gene Name
blaCTX-M-9a
Uniprot ID
Q9L5C8
Uniprot Name
Beta-lactamase
Molecular Weight
30951.03 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 15:32 / Updated on December 01, 2017 16:06