Identification
Name2-{1-[2-Amino-2-(4-Hydroxy-Phenyl)-Acetylamino]-2-Oxo-Ethyl}-5,5-Dimethyl-Thiazolidine-4-Carboxylic Acid
Accession NumberDB03658  (EXPT00594)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 367.42
Monoisotopic: 367.120191487
Chemical FormulaC16H21N3O5S
InChI KeySMLJDSWXGVMNTH-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][C@](N)(C(O)=N[C@]([H])(C=O)[C@]1([H])N[C@@]([H])(C(O)=O)C(C)(C)S1)C1=CC=C(O)C=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Beta-lactamaseProteinunknownNot AvailableEscherichia coli (strain K12)P00811 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative ParentsPhenylacetamides / 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
SubstituentsAlpha-amino acid amide / Phenylacetamide / D-alpha-amino acid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Amino acid
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsthiazolidinemonocarboxylic 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
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 June 11, 2017 20:49