NAV

(2R,4S)-2-[(1R)-1-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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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
PubChem Compound
5287717
PubChem Substance
46505457
ChemSpider
4450029
ZINC
ZINC000033821208
PDBe Ligand
AXL
PDB Entries
1ll9 / 3n7w / 4ebn / 6i1e / 6i1f / 6kgv

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
logP-2.5Chemaxon
pKa (Strongest Acidic)2.86Chemaxon
pKa (Strongest Basic)7.51Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area141.75 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity91.66 m3·mol-1Chemaxon
Polarizability36.12 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-MSsplash10-00di-0900000000-11c35aa33569792eace9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-475ac77d8e624a5e1bcb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0069000000-c49c324cbf3e3cb095ba
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-3985000000-2477a7c497bfde6bc5c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03kc-0900000000-84c5a4cd7e951927d258
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-4940000000-f43cf7c810b51e9efd5e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-a0c09392dff9c2370360
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.65547
predicted
DeepCCS 1.0 (2019)
[M+H]+183.51646
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.12228
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52