(1R)-1-(2-thienylacetylamino)-1-phenylmethylboronic acid

Identification

Name
(1R)-1-(2-thienylacetylamino)-1-phenylmethylboronic acid
Accession Number
DB08552
Type
Small Molecule
Groups
Experimental
Description

(1R)-1-(2-thienylacetylamino)-1-phenylmethylboronic acid is a solid. This compound belongs to the benzenes and substituted derivatives. These are aromatic compounds containing at least one benzene ring. This medication targets the protein beta-lactamase.

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 275.131
Monoisotopic: 275.078744475
Chemical Formula
C13H14BNO3S
InChI Key
LGJCDEZMANATFA-ZDUSSCGKSA-N
InChI
InChI=1S/C13H14BNO3S/c16-12(9-11-7-4-8-19-11)15-13(14(17)18)10-5-2-1-3-6-10/h1-8,13,17-18H,9H2,(H,15,16)/t13-/m0/s1
IUPAC Name
[(R)-phenyl[2-(thiophen-2-yl)acetamido]methyl]boronic acid
SMILES
[H][[email protected]@](NC(=O)CC1=CC=CS1)(B(O)O)C1=CC=CC=C1

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
5289378
PubChem Substance
99445023
ChemSpider
4451364
ChEMBL
CHEMBL404155
HET
SM3
PDB Entries
1my8 / 1pi4 / 2ffy

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 Solubility0.0373 mg/mLALOGPS
logP1.78ALOGPS
logP2.78ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.72ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.27 m3·mol-1ChemAxon
Polarizability28.59 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6993
Blood Brain Barrier+0.9073
Caco-2 permeable-0.5853
P-glycoprotein substrateNon-substrate0.7087
P-glycoprotein inhibitor INon-inhibitor0.9743
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9281
CYP450 2C9 substrateNon-substrate0.5358
CYP450 2D6 substrateNon-substrate0.7951
CYP450 3A4 substrateNon-substrate0.6787
CYP450 1A2 substrateNon-inhibitor0.7551
CYP450 2C9 inhibitorNon-inhibitor0.7961
CYP450 2D6 inhibitorNon-inhibitor0.9208
CYP450 2C19 inhibitorNon-inhibitor0.704
CYP450 3A4 inhibitorNon-inhibitor0.8448
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6962
Ames testNon AMES toxic0.6686
CarcinogenicityNon-carcinogens0.8123
BiodegradationNot ready biodegradable0.7684
Rat acute toxicity2.3161 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9914
hERG inhibition (predictor II)Non-inhibitor0.947
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 benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Boronic acids / Organic metalloid salts / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Monoalkylboranes / Hydrocarbon derivatives
show 1 more
Substituents
Monocyclic benzene moiety / Thiophene / Heteroaromatic compound / Boronic acid derivative / Boronic acid / Carboxamide group / Secondary carboxylic acid amide / Organic metalloid salt / Organoheterocyclic compound / Carboxylic acid derivative
show 13 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 15:32 / Updated on December 01, 2017 16:06