NAV

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

Identification

Generic Name
(1R)-1-(2-thienylacetylamino)-1-phenylmethylboronic acid
DrugBank Accession Number
DB08552
Background

(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.

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 275.131
Monoisotopic: 275.078744475
Chemical Formula
C13H14BNO3S
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 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
Alkylborane / Aromatic heteromonocyclic compound / Boronic acid / Boronic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monoalkylborane
show 13 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
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][C@@](NC(=O)CC1=CC=CS1)(B(O)O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5289378
PubChem Substance
99445023
ChemSpider
4451364
ChEMBL
CHEMBL404155
ZINC
ZINC000169748509
PDBe Ligand
SM3
PDB Entries
1my8 / 1pi4 / 2ffy

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 Solubility0.0373 mg/mLALOGPS
logP1.78ALOGPS
logP2.78Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.59Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
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-MSsplash10-0002-9210000000-e6c2e5cc31f2fb764bbc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0290000000-7dee132449c58b290b77
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kwg-9740000000-60478919919ec02b800a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-054k-5290000000-1ad412ea47102ae9c1ed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-eae9680c60ffaeca27b9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-683e8fe61f3d05ae91bd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000w-9510000000-6aaa19ab01b59ca3e22c
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

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 21:32 / Updated at June 12, 2020 16:52