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

Identification

Name
2-[(1R)-1-carboxy-2-naphthalen-1-ylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
Accession Number
DB06922
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: 389.3576
Monoisotopic: 389.089937217
Chemical Formula
C22H15NO6
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][[email protected]](CC1=CC=CC2=CC=CC=C12)(N1C(=O)C2=CC=C(C=C2C1=O)C(O)=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
16752640
PubChem Substance
99443393
ChemSpider
23317723
BindingDB
41850
ChEBI
92659
ChEMBL
CHEMBL405886
HET
23C
PDB Entries
2r9w

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 Solubility0.00674 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/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 / 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
show 2 more
Substituents
Phthalimide / Alpha-amino acid or derivatives / Naphthalene / Isoindole / Dicarboxylic acid or derivatives / Benzenoid / Carboxylic acid imide, n-substituted / Carboxylic acid imide / Carboxylic acid derivative / Carboxylic acid
show 10 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 15:17 / Updated on December 01, 2017 15:43