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

Identification

Name
2-{1-[2-(2-Amino-Thiazol-4-Yl)-2-Methoxyimino-Acetylamino]-2-Oxo-Ethyl}-5,5-Dimethyl-Thiazolidine-4-Carboxylic Acid
Accession Number
DB03437  (EXPT02521)
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: 401.461
Monoisotopic: 401.082760123
Chemical Formula
C14H19N5O5S2
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)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
SMILES
[H][[email protected]](C=O)(N=C(O)C(=N/OC)\C1=CSC(=N)N1)[[email protected]]1([H])N[[email protected]@]([H])(C(O)=O)C(C)(C)S1

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
9600418
PubChem Substance
46507263
ChemSpider
7874557
HET
PCN
PDB Entries
1llb

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 Solubility0.214 mg/mLALOGPS
logP0.37ALOGPS
logP-2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.63ChemAxon
pKa (Strongest Basic)6.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.46 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.2 m3·mol-1ChemAxon
Polarizability38.52 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, 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 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
D-alpha-amino acid / 2,4-disubstituted 1,3-thiazole / 1,3-thiazol-2-amine / Azole / Heteroaromatic compound / Thiazole / Thiazolidine / Carboxamide group / Amino acid / Secondary carboxylic acid amide
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-thiazole, thiazolidinemonocarboxylic acid (CHEBI:44840)

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 15:13