(2R)-2-{(1R)-2-oxo-1-[(2-thienylacetyl)amino]ethyl}-5,6-dihydro-2h-1,3-thiazine-4-carboxylic acid

Identification

Name
(2R)-2-{(1R)-2-oxo-1-[(2-thienylacetyl)amino]ethyl}-5,6-dihydro-2h-1,3-thiazine-4-carboxylic acid
Accession Number
DB04742
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: 326.391
Monoisotopic: 326.039498326
Chemical Formula
C13H14N2O4S2
InChI Key
QIZKCGBBVPUBJL-ZYHUDNBSSA-N
InChI
InChI=1S/C13H14N2O4S2/c16-7-10(12-15-9(13(18)19)3-5-21-12)14-11(17)6-8-2-1-4-20-8/h1-2,4,7,10,12H,3,5-6H2,(H,14,17)(H,18,19)/t10-,12-/m1/s1
IUPAC Name
(2R)-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
SMILES
[H][C@@](NC(=O)CC1=CC=CS1)(C=O)[C@@]1([H])SCCC(=N1)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UD-alanyl-D-alanine carboxypeptidaseNot AvailableActinomadura sp. (strain R39)
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
5288990
PubChem Substance
46505603
ChemSpider
4451047
HET
NCF
PDB Entries
1w8y

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 Solubility0.0551 mg/mLALOGPS
logP0.93ALOGPS
logP1.43ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.83 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.94 m3·mol-1ChemAxon
Polarizability30.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9358
Blood Brain Barrier-0.6466
Caco-2 permeable-0.7235
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9593
P-glycoprotein inhibitor IINon-inhibitor0.9912
Renal organic cation transporterNon-inhibitor0.81
CYP450 2C9 substrateNon-substrate0.7996
CYP450 2D6 substrateNon-substrate0.8192
CYP450 3A4 substrateNon-substrate0.6767
CYP450 1A2 substrateNon-inhibitor0.8259
CYP450 2C9 inhibitorNon-inhibitor0.9007
CYP450 2D6 inhibitorNon-inhibitor0.911
CYP450 2C19 inhibitorNon-inhibitor0.9152
CYP450 3A4 inhibitorNon-inhibitor0.9103
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9561
Ames testNon AMES toxic0.8375
CarcinogenicityNon-carcinogens0.9457
BiodegradationNot ready biodegradable0.8685
Rat acute toxicity2.1491 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9954
hERG inhibition (predictor II)Non-inhibitor0.9364
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 1,3-thiazines. These are organic compounds containing 1,3-thiazine, a six-member ring with a nitrogen and a sulfur atoms in ring positions 1 and 3 respectively, as well as two double bonds.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiazines
Sub Class
1,3-thiazines
Direct Parent
1,3-thiazines
Alternative Parents
Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Meta-thiazine / Thiophene / Heteroaromatic compound / Carboxamide group / Ketimine / Secondary carboxylic acid amide / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Thioether
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiazinemonocarboxylic acid (CHEBI:44267)

Targets

Kind
Protein
Organism
Actinomadura sp. (strain R39)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name
dac
Uniprot ID
P39045
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
54973.425 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 11, 2007 11:49 / Updated on November 02, 2018 06:04