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(2R,4S)-2-[(1R)-1-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)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-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
DrugBank Accession Number
DB03437
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 401.461
Monoisotopic: 401.082760123
Chemical Formula
C14H19N5O5S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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 d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
D-alpha-amino acids
Alternative Parents
2,4-disubstituted thiazoles / 2-amino-1,3-thiazoles / Thiazolidines / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Thiohemiaminal derivatives / Secondary amines / Azacyclic compounds / Carboxylic acids
show 6 more
Substituents
1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Aldehyde / Amine / Amino acid / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-thiazole, thiazolidinemonocarboxylic acid (CHEBI:44840)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YVNKGXXVZIQNIV-RKMXGKDGSA-N
InChI
InChI=1S/C14H19N5O5S2/c1-14(2)9(12(22)23)18-11(26-14)6(4-20)16-10(21)8(19-24-3)7-5-25-13(15)17-7/h4-6,9,11,18H,1-3H3,(H2,15,17)(H,16,21)(H,22,23)/b19-8-/t6-,9+,11-/m1/s1
IUPAC Name
(2R,4S)-2-[(1R)-1-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
SMILES
[H]N([H])C1=NC(=CS1)C(=N\OC)\C(=O)N([H])[C@H](C=O)[C@@]1([H])SC(C)(C)[C@@H](N1[H])C(O)=O

References

General References
Not Available
PubChem Compound
9600418
PubChem Substance
46507263
ChemSpider
7874557
ZINC
ZINC000033396878
PDBe Ligand
PCN
PDB Entries
1llb

Clinical Trials

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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 Solubility0.138 mg/mLALOGPS
logP-0.07ALOGPS
logP-2.2Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.78Chemaxon
pKa (Strongest Basic)7.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area156 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity94.88 m3·mol-1Chemaxon
Polarizability38.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6822
Blood Brain Barrier-0.8543
Caco-2 permeable-0.6043
P-glycoprotein substrateNon-substrate0.5988
P-glycoprotein inhibitor INon-inhibitor0.8758
P-glycoprotein inhibitor IINon-inhibitor0.9264
Renal organic cation transporterNon-inhibitor0.9628
CYP450 2C9 substrateNon-substrate0.8534
CYP450 2D6 substrateNon-substrate0.8242
CYP450 3A4 substrateNon-substrate0.5975
CYP450 1A2 substrateNon-inhibitor0.6691
CYP450 2C9 inhibitorNon-inhibitor0.6794
CYP450 2D6 inhibitorNon-inhibitor0.8918
CYP450 2C19 inhibitorNon-inhibitor0.7167
CYP450 3A4 inhibitorNon-inhibitor0.8689
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9363
Ames testNon AMES toxic0.5481
CarcinogenicityNon-carcinogens0.7093
BiodegradationNot ready biodegradable0.9957
Rat acute toxicity2.7592 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9989
hERG inhibition (predictor II)Non-inhibitor0.9181
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 MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05di-0109000000-9566e227d9bc60acebe0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0940400000-893d13172f2ac668a353
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0591000000-6084d780ab17d3aedc3e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00du-3796000000-ae40b964c3e80517e428
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0955000000-a4e3906148fee83bd8bd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00g3-3910000000-2101bc374ab84f8ce868
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]-191.03123
predicted
DeepCCS 1.0 (2019)
[M+H]+193.01894
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.31181
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