(2R,4S)-2-[(1R)-1-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
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Identification
- Generic Name
- (2R,4S)-2-[(1R)-1-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
- DrugBank Accession Number
- DB03658
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 367.42
Monoisotopic: 367.120191487 - Chemical Formula
- C16H21N3O5S
- Synonyms
- (2R,4S)-2-[(1R)-1-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBeta-lactamase Not Available Escherichia 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Aldehyde / Alpha-amino acid amide / Amine / Amino acid / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- thiazolidinemonocarboxylic acid (CHEBI:40985)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- 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-2-(4-hydroxyphenyl)acetamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
- SMILES
- [H]N([H])[C@@H](C(=O)N([H])[C@H](C=O)[C@@]1([H])SC(C)(C)[C@@H](N1[H])C(O)=O)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287717
- PubChem Substance
- 46505457
- ChemSpider
- 4450029
- ZINC
- ZINC000033821208
- PDBe Ligand
- AXL
- PDB Entries
- 1ll9 / 3n7w / 4ebn / 6i1e / 6i1f / 6kgv
Clinical Trials
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
Property Value Source logP -2.5 Chemaxon pKa (Strongest Acidic) 2.86 Chemaxon pKa (Strongest Basic) 7.51 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 141.75 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 91.66 m3·mol-1 Chemaxon Polarizability 36.12 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.605 Blood Brain Barrier - 0.9542 Caco-2 permeable - 0.7654 P-glycoprotein substrate Substrate 0.5153 P-glycoprotein inhibitor I Non-inhibitor 0.9655 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.9667 CYP450 2C9 substrate Non-substrate 0.844 CYP450 2D6 substrate Non-substrate 0.8113 CYP450 3A4 substrate Non-substrate 0.616 CYP450 1A2 substrate Non-inhibitor 0.88 CYP450 2C9 inhibitor Non-inhibitor 0.8602 CYP450 2D6 inhibitor Non-inhibitor 0.9315 CYP450 2C19 inhibitor Non-inhibitor 0.89 CYP450 3A4 inhibitor Non-inhibitor 0.916 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.934 Ames test Non AMES toxic 0.8817 Carcinogenicity Non-carcinogens 0.7637 Biodegradation Not ready biodegradable 0.9823 Rat acute toxicity 2.1206 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9992 hERG inhibition (predictor II) Non-inhibitor 0.9417
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-0900000000-11c35aa33569792eace9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-475ac77d8e624a5e1bcb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0069000000-c49c324cbf3e3cb095ba Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-3985000000-2477a7c497bfde6bc5c6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03kc-0900000000-84c5a4cd7e951927d258 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-4940000000-f43cf7c810b51e9efd5e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0900000000-a0c09392dff9c2370360 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.65547 predictedDeepCCS 1.0 (2019) [M+H]+ 183.51646 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.12228 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsBeta-lactamase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52