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

Identification

Generic Name
2-[CARBOXY-(2-THIOPHEN-2-YL-ACETYLAMINO)-METHYL]-5-METHYLENE-5,6-DIHYDRO-2H-[1,3]THIAZINE-4-CARBOXYLIC ACID
DrugBank Accession Number
DB08623
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 354.401
Monoisotopic: 354.034412948
Chemical Formula
C14H14N2O5S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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 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
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Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid / Dicarboxylic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / Meta-thiazine / N-acyl-l-alpha-amino acid
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiophenes, thiazinemonocarboxylic acid, 1,3-thiazine (CHEBI:45976)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@](NC(=O)CC1=CC=CS1)(C(O)=O)C1=N[C@]([H])(C(O)=O)C(=C)CS1

References

General References
Not Available
PubChem Compound
46937164
PubChem Substance
99445094
ChemSpider
25057866
ZINC
ZINC000006293333
PDBe Ligand
THN
PDB Entries
1kvl

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

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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. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52