1(R)-1-ACETAMIDO-2-(3-CARBOXY-2-HYDROXYPHENYL)ETHYL BORONIC ACID

Identification

Generic Name
1(R)-1-ACETAMIDO-2-(3-CARBOXY-2-HYDROXYPHENYL)ETHYL BORONIC ACID
DrugBank Accession Number
DB07464
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 267.043
Monoisotopic: 267.091417651
Chemical Formula
C11H14BNO6
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamase TEMNot 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

Adverse Effects
Adverseeffects
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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 salicylic acids. These are ortho-hydroxylated benzoic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Salicylic acids
Alternative Parents
Benzoic acids / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / Vinylogous acids / Acetamides / Secondary carboxylic acid amides / Boronic acids / Organic metalloid salts / Monocarboxylic acids and derivatives / Carboxylic acids
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Substituents
1-hydroxy-4-unsubstituted benzenoid / Acetamide / Alkylborane / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl / Boronic acid / Boronic acid derivative / Carbonyl group / Carboxamide group
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MSRKDROGGGBNIX-VIFPVBQESA-N
InChI
InChI=1S/C11H14BNO6/c1-6(14)13-9(12(18)19)5-7-3-2-4-8(10(7)15)11(16)17/h2-4,9,15,18-19H,5H2,1H3,(H,13,14)(H,16,17)/t9-/m0/s1
IUPAC Name
3-[(2R)-2-(dihydroxyboranyl)-2-acetamidoethyl]-2-hydroxybenzoic acid
SMILES
[H][C@@](CC1=CC=CC(C(O)=O)=C1O)(NC(C)=O)B(O)O

References

General References
Not Available
PubChem Compound
5287794
PubChem Substance
99443935
ChemSpider
4450092
ZINC
ZINC000169748495
PDBe Ligand
BJH
PDB Entries
1erq

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 Solubility0.68 mg/mLALOGPS
logP-0.16ALOGPS
logP1.25ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.66 m3·mol-1ChemAxon
Polarizability25.96 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6775
Blood Brain Barrier+0.5441
Caco-2 permeable-0.7116
P-glycoprotein substrateNon-substrate0.6277
P-glycoprotein inhibitor INon-inhibitor0.9803
P-glycoprotein inhibitor IINon-inhibitor0.9967
Renal organic cation transporterNon-inhibitor0.9566
CYP450 2C9 substrateNon-substrate0.618
CYP450 2D6 substrateNon-substrate0.8116
CYP450 3A4 substrateNon-substrate0.5833
CYP450 1A2 substrateNon-inhibitor0.8259
CYP450 2C9 inhibitorNon-inhibitor0.8654
CYP450 2D6 inhibitorNon-inhibitor0.9193
CYP450 2C19 inhibitorNon-inhibitor0.8947
CYP450 3A4 inhibitorNon-inhibitor0.9019
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9719
Ames testNon AMES toxic0.7542
CarcinogenicityNon-carcinogens0.8923
BiodegradationReady biodegradable0.5515
Rat acute toxicity2.2903 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.972
hERG inhibition (predictor II)Non-inhibitor0.9319
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

Targets

Drugtargets2
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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. [Article]

Drug created on September 15, 2010 21:22 / Updated on June 12, 2020 16:52