NAV

2-[(1R)-1-carboxy-2-naphthalen-1-ylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Identification

Generic Name
2-[(1R)-1-carboxy-2-naphthalen-1-ylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
DrugBank Accession Number
DB06922
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 389.3576
Monoisotopic: 389.089937217
Chemical Formula
C22H15NO6
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 phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Phthalimides
Alternative Parents
Naphthalenes / Alpha amino acids and derivatives / Isoindoles / N-substituted carboxylic acid imides / Dicarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
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Substituents
Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Dicarboxylic acid or derivatives
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CZNPWASYMRBJCX-GOSISDBHSA-N
InChI
InChI=1S/C22H15NO6/c24-19-16-9-8-14(21(26)27)10-17(16)20(25)23(19)18(22(28)29)11-13-6-3-5-12-4-1-2-7-15(12)13/h1-10,18H,11H2,(H,26,27)(H,28,29)/t18-/m1/s1
IUPAC Name
2-[(1R)-1-carboxy-2-(naphthalen-1-yl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
SMILES
[H][C@](CC1=CC=CC2=CC=CC=C12)(N1C(=O)C2=CC=C(C=C2C1=O)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
16752640
PubChem Substance
99443393
ChemSpider
23317723
BindingDB
41850
ChEBI
92659
ChEMBL
CHEMBL405886
PDBe Ligand
23C
PDB Entries
2r9w

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 Solubility0.00674 mg/mLALOGPS
logP2.33ALOGPS
logP3.27Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.07Chemaxon
pKa (Strongest Basic)-7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area111.98 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity103.12 m3·mol-1Chemaxon
Polarizability39.03 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9637
Blood Brain Barrier+0.9225
Caco-2 permeable-0.5737
P-glycoprotein substrateNon-substrate0.6637
P-glycoprotein inhibitor INon-inhibitor0.9699
P-glycoprotein inhibitor IINon-inhibitor0.9007
Renal organic cation transporterNon-inhibitor0.8305
CYP450 2C9 substrateNon-substrate0.7437
CYP450 2D6 substrateNon-substrate0.8275
CYP450 3A4 substrateNon-substrate0.5908
CYP450 1A2 substrateNon-inhibitor0.9383
CYP450 2C9 inhibitorNon-inhibitor0.9607
CYP450 2D6 inhibitorNon-inhibitor0.872
CYP450 2C19 inhibitorNon-inhibitor0.941
CYP450 3A4 inhibitorNon-inhibitor0.9635
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9509
Ames testNon AMES toxic0.8616
CarcinogenicityNon-carcinogens0.9368
BiodegradationNot ready biodegradable0.7221
Rat acute toxicity2.3377 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9905
hERG inhibition (predictor II)Non-inhibitor0.9506
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0209000000-21ac76d20be90c21dda7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-0907000000-eb20ed51dd56b27d5746
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0096-0609000000-21d1344cd6c590084a48
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0119000000-0e4de0f758140c2946fd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052g-0900000000-20204d605e5b9e5fd1b4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-1900000000-b9ed06f1483285913153
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.19069
predicted
DeepCCS 1.0 (2019)
[M+H]+188.58144
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.64183
predicted
DeepCCS 1.0 (2019)

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 21:17 / Updated at June 12, 2020 16:52