2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID

Identification

Name
2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID
Accession Number
DB07663
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: 355.2983
Monoisotopic: 355.069201775
Chemical Formula
C18H13NO7
InChI Key
QISJEFYTLZTWIQ-CQSZACIVSA-N
InChI
InChI=1S/C18H13NO7/c20-11-4-1-9(2-5-11)7-14(18(25)26)19-15(21)12-6-3-10(17(23)24)8-13(12)16(19)22/h1-6,8,14,20H,7H2,(H,23,24)(H,25,26)/t14-/m1/s1
IUPAC Name
2-[(1R)-1-carboxy-2-(4-hydroxyphenyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
SMILES
[H][[email protected]](CC1=CC=C(O)C=C1)(N1C(=O)C2=C(C=C(C=C2)C(O)=O)C1=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
7013169
PubChem Substance
99444134
ChemSpider
5376302
ChEMBL
CHEMBL264702
HET
DK2
PDB Entries
2pu2

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 Solubility0.0521 mg/mLALOGPS
logP1.58ALOGPS
logP1.97ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area132.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.65 m3·mol-1ChemAxon
Polarizability34.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9738
Blood Brain Barrier+0.9243
Caco-2 permeable-0.6029
P-glycoprotein substrateNon-substrate0.6508
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.8487
Renal organic cation transporterNon-inhibitor0.8066
CYP450 2C9 substrateNon-substrate0.7609
CYP450 2D6 substrateNon-substrate0.8164
CYP450 3A4 substrateNon-substrate0.5468
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9313
CYP450 2D6 inhibitorNon-inhibitor0.543
CYP450 2C19 inhibitorNon-inhibitor0.93
CYP450 3A4 inhibitorNon-inhibitor0.9482
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.8296
CarcinogenicityNon-carcinogens0.9324
BiodegradationReady biodegradable0.5194
Rat acute toxicity2.4263 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.9294
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phthalimides / Phenylpropanoic acids / Amphetamines and derivatives / Isoindoles / 1-hydroxy-2-unsubstituted benzenoids / N-substituted carboxylic acid imides / Dicarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
Tyrosine or derivatives / Phenylalanine or derivatives / Phthalimide / 3-phenylpropanoic-acid / Amphetamine or derivatives / Isoindolone / Isoindoline / Isoindole / Isoindole or derivatives / 1-hydroxy-2-unsubstituted benzenoid
show 18 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 15:24 / Updated on December 01, 2017 15:54