Identification

Generic Name
[(2-Ethoxy-1-Naphthoyl)Amino]Methylboronic Acid
DrugBank Accession Number
DB02841
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 273.092
Monoisotopic: 273.117238471
Chemical Formula
C14H16BNO4
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-lactamaseNot AvailableEscherichia coli
UBeta-lactamase TEMNot AvailableSalmonella typhi
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
Improve decision support & research outcomes
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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 naphthalenecarboxamides. These are compounds containing a naphthalene moiety, which bears a carboxylic acid amide group at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthalenecarboxylic acids and derivatives
Direct Parent
Naphthalenecarboxamides
Alternative Parents
Alkyl aryl ethers / Secondary carboxylic acid amides / Boronic acids / Organic metalloid salts / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Monoalkylboranes / Hydrocarbon derivatives
Substituents
1-naphthalenecarboxamide / Alkyl aryl ether / Alkylborane / Aromatic homopolycyclic compound / Boronic acid / Boronic acid derivative / Carboxamide group / Carboxylic acid derivative / Ether / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VGXJNGVFESCMME-UHFFFAOYSA-N
InChI
InChI=1S/C14H16BNO4/c1-2-20-12-8-7-10-5-3-4-6-11(10)13(12)14(17)16-9-15(18)19/h3-8,18-19H,2,9H2,1H3,(H,16,17)
IUPAC Name
{[(2-ethoxynaphthalen-1-yl)formamido]methyl}boronic acid
SMILES
CCOC1=C(C(=O)NCB(O)O)C2=C(C=CC=C2)C=C1

References

General References
Not Available
PubChem Compound
5288987
PubChem Substance
46508531
ChemSpider
4451044
BindingDB
39812
ChEMBL
CHEMBL1234635
ZINC
ZINC000169748477
PDBe Ligand
NBF
PDB Entries
1ny0 / 1yms

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 Solubility0.0815 mg/mLALOGPS
logP1.45ALOGPS
logP2.21ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.79 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.55 m3·mol-1ChemAxon
Polarizability28.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9355
Blood Brain Barrier-0.7913
Caco-2 permeable-0.6366
P-glycoprotein substrateSubstrate0.5682
P-glycoprotein inhibitor INon-inhibitor0.7682
P-glycoprotein inhibitor IINon-inhibitor0.9804
Renal organic cation transporterNon-inhibitor0.922
CYP450 2C9 substrateNon-substrate0.6898
CYP450 2D6 substrateNon-substrate0.7719
CYP450 3A4 substrateNon-substrate0.535
CYP450 1A2 substrateInhibitor0.6264
CYP450 2C9 inhibitorNon-inhibitor0.7308
CYP450 2D6 inhibitorNon-inhibitor0.7974
CYP450 2C19 inhibitorNon-inhibitor0.6259
CYP450 3A4 inhibitorNon-inhibitor0.5416
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5159
Ames testNon AMES toxic0.5686
CarcinogenicityNon-carcinogens0.7383
BiodegradationNot ready biodegradable0.9028
Rat acute toxicity2.3963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9301
hERG inhibition (predictor II)Non-inhibitor0.5657
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
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. [Article]
Kind
Protein
Organism
Salmonella typhi
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific 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 cephalos...
Gene Name
bla
Uniprot ID
P62594
Uniprot Name
Beta-lactamase TEM
Molecular Weight
31514.865 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52