NAV

(1R)-2-PHENYLACETAMIDO-2-(3-CARBOXYPHENYL)ETHYL BORONIC ACID

Identification

Generic Name
(1R)-2-PHENYLACETAMIDO-2-(3-CARBOXYPHENYL)ETHYL BORONIC ACID
DrugBank Accession Number
DB07466
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 327.14
Monoisotopic: 327.127803157
Chemical Formula
C17H18BNO5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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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 phenylacetamides. These are amide derivatives of phenylacetic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetamides
Direct Parent
Phenylacetamides
Alternative Parents
Benzoic acids / Benzoyl derivatives / Secondary carboxylic acid amides / Boronic acids / Organic metalloid salts / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 3 more
Substituents
Alkylborane / Aromatic homomonocyclic compound / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Boronic acid / Boronic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid
show 15 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
ZAHVYMBTUDWUAX-HNNXBMFYSA-N
InChI
InChI=1S/C17H18BNO5/c20-16(11-12-5-2-1-3-6-12)19-15(18(23)24)10-13-7-4-8-14(9-13)17(21)22/h1-9,15,23-24H,10-11H2,(H,19,20)(H,21,22)/t15-/m0/s1
IUPAC Name
3-[(2R)-2-(dihydroxyboranyl)-2-(2-phenylacetamido)ethyl]benzoic acid
SMILES
[H][C@@](CC1=CC=CC(=C1)C(O)=O)(NC(=O)CC1=CC=CC=C1)B(O)O

References

General References
Not Available
PubChem Compound
5287796
PubChem Substance
99443937
ChemSpider
4450094
ZINC
ZINC000169748496
PDBe Ligand
BJP
PDB Entries
1ero

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 Solubility0.0211 mg/mLALOGPS
logP1.37ALOGPS
logP2.73Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.04Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area106.86 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity84.4 m3·mol-1Chemaxon
Polarizability33.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6401
Blood Brain Barrier+0.8867
Caco-2 permeable-0.6648
P-glycoprotein substrateNon-substrate0.7238
P-glycoprotein inhibitor INon-inhibitor0.9404
P-glycoprotein inhibitor IINon-inhibitor0.9974
Renal organic cation transporterNon-inhibitor0.9381
CYP450 2C9 substrateNon-substrate0.696
CYP450 2D6 substrateNon-substrate0.8073
CYP450 3A4 substrateNon-substrate0.6329
CYP450 1A2 substrateNon-inhibitor0.8863
CYP450 2C9 inhibitorNon-inhibitor0.9054
CYP450 2D6 inhibitorNon-inhibitor0.9278
CYP450 2C19 inhibitorNon-inhibitor0.9345
CYP450 3A4 inhibitorNon-inhibitor0.8758
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9654
Ames testNon AMES toxic0.7257
CarcinogenicityNon-carcinogens0.8647
BiodegradationNot ready biodegradable0.6396
Rat acute toxicity2.0228 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9816
hERG inhibition (predictor II)Non-inhibitor0.935
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-MSsplash10-0007-9121000000-dae74c6f3b8c8f382a3c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0179000000-41ede6264df117178b16
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2692000000-c690b660c58845f8e373
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9000000000-d27cfc1d8a2997fdfc76
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0296-3931000000-ba1cbd8784384c344515
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-9240000000-f9fc0fc8699c1c97520a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9521000000-5f429a4170965fd37210
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Beta-lactamase TEM
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 at September 15, 2010 21:22 / Updated at June 12, 2020 16:52