(3S)-1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Identification

Name
(3S)-1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
Accession Number
DB07057
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: 221.2093
Monoisotopic: 221.068807845
Chemical Formula
C11H11NO4
InChI Key
FPQOSKXLHCTVED-ZETCQYMHSA-N
InChI
InChI=1S/C11H11NO4/c13-9-4-2-1-3-8(9)12-6-7(11(15)16)5-10(12)14/h1-4,7,13H,5-6H2,(H,15,16)/t7-/m0/s1
IUPAC Name
(3S)-1-(2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
SMILES
[H][[email protected]]1(CN(C(=O)C1)C1=C(O)C=CC=C1)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
756618
PubChem Substance
99443528
ChemSpider
661833
HET
3GV
PDB Entries
3gvb

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 Solubility15.8 mg/mLALOGPS
logP0.72ALOGPS
logP0.38ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.84 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55 m3·mol-1ChemAxon
Polarizability21.43 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9449
Blood Brain Barrier+0.8459
Caco-2 permeable-0.6391
P-glycoprotein substrateNon-substrate0.6921
P-glycoprotein inhibitor INon-inhibitor0.9454
P-glycoprotein inhibitor IINon-inhibitor0.9181
Renal organic cation transporterNon-inhibitor0.8643
CYP450 2C9 substrateNon-substrate0.7634
CYP450 2D6 substrateNon-substrate0.8333
CYP450 3A4 substrateSubstrate0.5378
CYP450 1A2 substrateNon-inhibitor0.9118
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.8961
CYP450 2C19 inhibitorNon-inhibitor0.9089
CYP450 3A4 inhibitorNon-inhibitor0.9951
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9424
Ames testNon AMES toxic0.8419
CarcinogenicityNon-carcinogens0.9323
BiodegradationReady biodegradable0.6958
Rat acute toxicity2.3255 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9825
hERG inhibition (predictor II)Non-inhibitor0.8783
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 phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Pyrrolidine carboxylic acids / Oxoprolines / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Pyrrolidine-2-ones / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Pyrroles / Lactams / Azacyclic compounds
show 7 more
Substituents
1-phenylpyrrolidine / Oxoproline / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine carboxylic acid / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid / 2-pyrrolidone
show 18 more
Molecular Framework
Aromatic heteromonocyclic 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 15:18 / Updated on December 01, 2017 15:45