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

Identification

Name
2-[(1R)-2-carboxy-1-(naphthalen-1-ylmethyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
Accession Number
DB08731
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 403.3842
Monoisotopic: 403.105587281
Chemical Formula
C23H17NO6
InChI Key
GPOKTQCDBPECSS-MRXNPFEDSA-N
InChI
InChI=1S/C23H17NO6/c25-20(26)12-16(10-14-6-3-5-13-4-1-2-7-17(13)14)24-21(27)18-9-8-15(23(29)30)11-19(18)22(24)28/h1-9,11,16H,10,12H2,(H,25,26)(H,29,30)/t16-/m1/s1
IUPAC Name
2-[(2R)-1-carboxy-3-(naphthalen-1-yl)propan-2-yl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
SMILES
[H][[email protected]](CC(O)=O)(CC1=CC=CC2=CC=CC=C12)N1C(=O)C2=CC=C(C=C2C1=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
24764434
PubChem Substance
99445202
ChemSpider
25058908
HET
WH6
PDB Entries
2r9x

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00646 mg/mLALOGPS
logP2.39ALOGPS
logP3.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.98 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.74 m3·mol-1ChemAxon
Polarizability40.76 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8458
Blood Brain Barrier+0.9248
Caco-2 permeable-0.5572
P-glycoprotein substrateNon-substrate0.6462
P-glycoprotein inhibitor INon-inhibitor0.9602
P-glycoprotein inhibitor IINon-inhibitor0.9552
Renal organic cation transporterNon-inhibitor0.8225
CYP450 2C9 substrateNon-substrate0.7058
CYP450 2D6 substrateNon-substrate0.8342
CYP450 3A4 substrateNon-substrate0.5327
CYP450 1A2 substrateNon-inhibitor0.8933
CYP450 2C9 inhibitorNon-inhibitor0.9441
CYP450 2D6 inhibitorNon-inhibitor0.931
CYP450 2C19 inhibitorNon-inhibitor0.9591
CYP450 3A4 inhibitorNon-inhibitor0.9353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9538
Ames testNon AMES toxic0.8678
CarcinogenicityNon-carcinogens0.9078
BiodegradationNot ready biodegradable0.7411
Rat acute toxicity2.3849 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9879
hERG inhibition (predictor II)Non-inhibitor0.9512
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/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

Taxonomy

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 / Isoindoles / N-substituted carboxylic acid imides / Dicarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Phthalimide / Naphthalene / Isoindole / Dicarboxylic acid or derivatives / Benzenoid / Carboxylic acid imide, n-substituted / Carboxylic acid imide / Carboxylic acid derivative / Carboxylic acid / Azacycle
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:10592235]

Drug created on September 15, 2010 15:34 / Updated on December 01, 2017 16:08