NAV

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

Identification

Generic Name
(2R)-2-{(1R)-2-oxo-1-[(2-thienylacetyl)amino]ethyl}-5,6-dihydro-2h-1,3-thiazine-4-carboxylic acid
DrugBank Accession Number
DB04742
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 326.391
Monoisotopic: 326.039498326
Chemical Formula
C13H14N2O4S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
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Substituents
Aldehyde / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiazinemonocarboxylic acid (CHEBI:44267)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
5288990
PubChem Substance
46505603
ChemSpider
4451047
ZINC
ZINC000012504489
PDBe Ligand
NCF
PDB Entries
1w8y

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 Solubility0.0551 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-MSsplash10-000y-9340000000-d712ab674426aaca90ec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0519000000-b0d6b7b3029f8baf8fd8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-0290000000-89b4048b1757d3dd737b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udu-1931000000-596739b3f729a55fec91
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-005c-3950000000-a25fbde51210a216fa2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-4960000000-bed0a9c7240ff64e5ff6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000w-9820000000-c3ba70f989c8d38900d1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-166.82874
predicted
DeepCCS 1.0 (2019)
[M+H]+169.18709
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.40048
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. D-alanyl-D-alanine carboxypeptidase
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. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52