2-{1-[2-Amino-2-(4-Hydroxy-Phenyl)-Acetylamino]-2-Oxo-Ethyl}-5,5-Dimethyl-Thiazolidine-4-Carboxylic Acid

Identification

Name
2-{1-[2-Amino-2-(4-Hydroxy-Phenyl)-Acetylamino]-2-Oxo-Ethyl}-5,5-Dimethyl-Thiazolidine-4-Carboxylic Acid
Accession Number
DB03658  (EXPT00594)
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: 367.42
Monoisotopic: 367.120191487
Chemical Formula
C16H21N3O5S
InChI Key
SMLJDSWXGVMNTH-NRWUCQMLSA-N
InChI
InChI=1S/C16H21N3O5S/c1-16(2)12(15(23)24)19-14(25-16)10(7-20)18-13(22)11(17)8-3-5-9(21)6-4-8/h3-7,10-12,14,19,21H,17H2,1-2H3,(H,18,22)(H,23,24)/t10-,11-,12+,14-/m1/s1
IUPAC Name
(2R,4S)-2-[(1R)-1-{[(2R)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
SMILES
[H][[email protected]](N)(C(O)=N[[email protected]]([H])(C=O)[[email protected]]1([H])N[[email protected]@]([H])(C(O)=O)C(C)(C)S1)C1=CC=C(O)C=C1

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
5287717
PubChem Substance
46505457
ChemSpider
4450029
HET
AXL
PDB Entries
1ll9 / 3n7w / 4ebn

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 Solubility0.347 mg/mLALOGPS
logP-0.63ALOGPS
logP-3.2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)8.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.18 m3·mol-1ChemAxon
Polarizability36.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.605
Blood Brain Barrier-0.9542
Caco-2 permeable-0.7654
P-glycoprotein substrateSubstrate0.5153
P-glycoprotein inhibitor INon-inhibitor0.9655
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9667
CYP450 2C9 substrateNon-substrate0.844
CYP450 2D6 substrateNon-substrate0.8113
CYP450 3A4 substrateNon-substrate0.616
CYP450 1A2 substrateNon-inhibitor0.88
CYP450 2C9 inhibitorNon-inhibitor0.8602
CYP450 2D6 inhibitorNon-inhibitor0.9315
CYP450 2C19 inhibitorNon-inhibitor0.89
CYP450 3A4 inhibitorNon-inhibitor0.916
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.934
Ames testNon AMES toxic0.8817
CarcinogenicityNon-carcinogens0.7637
BiodegradationNot ready biodegradable0.9823
Rat acute toxicity2.1206 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9992
hERG inhibition (predictor II)Non-inhibitor0.9417
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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Phenylacetamides / D-alpha-amino acids / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Thiazolidines / Secondary carboxylic acid amides / Amino acids / Thiohemiaminal derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds
show 6 more
Substituents
Alpha-amino acid amide / Phenylacetamide / D-alpha-amino acid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Amino acid
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiazolidinemonocarboxylic acid (CHEBI:40985)

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:16