Pinacol[[2-Amino-Alpha-(1-Carboxy-1-Methylethoxyimino)-4-Thiazoleacetyl]Amino]Methaneboronate

Identification

Name
Pinacol[[2-Amino-Alpha-(1-Carboxy-1-Methylethoxyimino)-4-Thiazoleacetyl]Amino]Methaneboronate
Accession Number
DB04035  (EXPT00840)
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: 330.125
Monoisotopic: 330.080535388
Chemical Formula
C10H15BN4O6S
InChI Key
ZECCQELUYUPTSB-UUASQNMZSA-N
InChI
InChI=1S/C10H15BN4O6S/c1-10(2,8(17)18)21-15-6(5-3-22-9(12)14-5)7(16)13-4-11(19)20/h3,19-20H,4H2,1-2H3,(H2,12,14)(H,13,16)(H,17,18)/b15-6-
IUPAC Name
2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(dihydroxyboranyl)methyl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid
SMILES
CC(C)(O\N=C(/C(=O)NCB(O)O)C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-lactamase CTX-MNot AvailableEscherichia coli
UBeta-lactamaseNot AvailableEscherichia coli (strain K12)
UBeta-lactamase TEMNot AvailableEscherichia coli
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
5849540
PubChem Substance
46505116
ChemSpider
4722090
BindingDB
50370963
ChEMBL
CHEMBL1231661
HET
CB4
PDB Entries
1iem / 1jwv / 1m40 / 1yly / 1ylz / 3mke / 4ua9 / 5chm / 5glb / 5gld

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 Solubility0.115 mg/mLALOGPS
logP0.16ALOGPS
logP-0.06ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)4.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area167.36 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity71.43 m3·mol-1ChemAxon
Polarizability31.59 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8861
Blood Brain Barrier-0.6297
Caco-2 permeable-0.6322
P-glycoprotein substrateSubstrate0.5176
P-glycoprotein inhibitor INon-inhibitor0.8712
P-glycoprotein inhibitor IINon-inhibitor0.9812
Renal organic cation transporterNon-inhibitor0.9557
CYP450 2C9 substrateNon-substrate0.8208
CYP450 2D6 substrateNon-substrate0.8058
CYP450 3A4 substrateNon-substrate0.5831
CYP450 1A2 substrateNon-inhibitor0.7403
CYP450 2C9 inhibitorNon-inhibitor0.7514
CYP450 2D6 inhibitorNon-inhibitor0.8851
CYP450 2C19 inhibitorNon-inhibitor0.6896
CYP450 3A4 inhibitorNon-inhibitor0.6334
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8756
Ames testNon AMES toxic0.5085
CarcinogenicityNon-carcinogens0.631
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity2.5996 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9988
hERG inhibition (predictor II)Non-inhibitor0.8531
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-MSNot Available
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 2,4-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at the positions 2 and 3.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Thiazoles
Direct Parent
2,4-disubstituted thiazoles
Alternative Parents
2-amino-1,3-thiazoles / Heteroaromatic compounds / Secondary carboxylic acid amides / Boronic acids / Amino acids / Organic metalloid salts / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Primary amines
show 5 more
Substituents
2,4-disubstituted 1,3-thiazole / 1,3-thiazol-2-amine / Heteroaromatic compound / Amino acid or derivatives / Boronic acid derivative / Boronic acid / Carboxamide group / Amino acid / Secondary carboxylic acid amide / Carboxylic acid derivative
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, monocarboxylic acid amide, 1,3-thiazole, boronic acids (CHEBI:41354)

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Beta-lactamase activity
Gene Name
blaCTX-M-14
Uniprot ID
Q9L5C7
Uniprot Name
Beta-lactamase
Molecular Weight
30979.09 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins. TEM-3 and TEM-4 are capable of hydrolyzing cefotaxime and ceftazidime. TEM-5 is capable of hydrolyzing ceftazidime. TEM-6 is capable of hydrolyzing ceftazidime and aztreonam. TEM-8/CAZ-2, TEM-16/CAZ-7 and TEM-24/CAZ-6 are markedly active against ceftazidime. IRT-4 shows resistance to beta-lactamase inhibitors.
Specific Function
Beta-lactamase activity
Gene Name
bla
Uniprot ID
P62593
Uniprot Name
Beta-lactamase TEM
Molecular Weight
31514.865 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:36