2-[CARBOXY-(2-THIOPHEN-2-YL-ACETYLAMINO)-METHYL]-5-METHYLENE-5,6-DIHYDRO-2H-[1,3]THIAZINE-4-CARBOXYLIC ACID

Identification

Name
2-[CARBOXY-(2-THIOPHEN-2-YL-ACETYLAMINO)-METHYL]-5-METHYLENE-5,6-DIHYDRO-2H-[1,3]THIAZINE-4-CARBOXYLIC ACID
Accession Number
DB08623
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: 354.401
Monoisotopic: 354.034412948
Chemical Formula
C14H14N2O5S2
InChI Key
VBBNCGUNWSPHOY-QWRGUYRKSA-N
InChI
InChI=1S/C14H14N2O5S2/c1-7-6-23-12(16-10(7)13(18)19)11(14(20)21)15-9(17)5-8-3-2-4-22-8/h2-4,10-11H,1,5-6H2,(H,15,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
IUPAC Name
(4S)-2-[(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl]-5-methylidene-5,6-dihydro-4H-1,3-thiazine-4-carboxylic acid
SMILES
[H][[email protected]@](NC(=O)CC1=CC=CS1)(C(O)=O)C1=N[[email protected]]([H])(C(O)=O)C(=C)CS1

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
46937164
PubChem Substance
99445094
ChemSpider
25057866
HET
THN
PDB Entries
1kvl

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 Solubility0.0534 mg/mLALOGPS
logP1.07ALOGPS
logP1.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.62ChemAxon
pKa (Strongest Basic)0.098ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.06 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.89 m3·mol-1ChemAxon
Polarizability32.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9799
Blood Brain Barrier-0.8346
Caco-2 permeable-0.6784
P-glycoprotein substrateSubstrate0.6192
P-glycoprotein inhibitor INon-inhibitor0.9131
P-glycoprotein inhibitor IINon-inhibitor0.9973
Renal organic cation transporterNon-inhibitor0.8543
CYP450 2C9 substrateNon-substrate0.8497
CYP450 2D6 substrateNon-substrate0.818
CYP450 3A4 substrateNon-substrate0.5984
CYP450 1A2 substrateNon-inhibitor0.758
CYP450 2C9 inhibitorNon-inhibitor0.7552
CYP450 2D6 inhibitorNon-inhibitor0.9035
CYP450 2C19 inhibitorNon-inhibitor0.7892
CYP450 3A4 inhibitorNon-inhibitor0.8473
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8825
Ames testNon AMES toxic0.7517
CarcinogenicityNon-carcinogens0.8819
BiodegradationNot ready biodegradable0.9522
Rat acute toxicity2.4412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9923
hERG inhibition (predictor II)Non-inhibitor0.9446
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 n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-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
N-acyl-L-alpha-amino acids
Alternative Parents
Dicarboxylic acids and derivatives / 1,3-thiazines / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
N-acyl-l-alpha-amino acid / Meta-thiazine / Dicarboxylic acid or derivatives / Thiophene / Heteroaromatic compound / Carboxamide group / Secondary carboxylic acid amide / Carboxylic acid / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiophenes, thiazinemonocarboxylic acid, 1,3-thiazine (CHEBI:45976)

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. 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 September 15, 2010 15:33 / Updated on December 01, 2017 16:07