Identification
Name2-[CARBOXY-(2-THIOPHEN-2-YL-ACETYLAMINO)-METHYL]-5-METHYLENE-5,6-DIHYDRO-2H-[1,3]THIAZINE-4-CARBOXYLIC ACID
Accession NumberDB08623
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: 354.401
Monoisotopic: 354.034412948
Chemical FormulaC14H14N2O5S2
InChI KeyVBBNCGUNWSPHOY-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
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 EntriesNot Available
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 Solubility0.0534 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-acyl-L-alpha-amino acids
Alternative ParentsDicarboxylic 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
SubstituentsN-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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsthiophenes, 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
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 June 11, 2017 21:19