(2R)-2-[(1R)-1-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-oxoethyl]-5-methylidene-2H-1,3-thiazine-4-carboxylic acid

Identification

Generic Name
(2R)-2-[(1R)-1-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-oxoethyl]-5-methylidene-2H-1,3-thiazine-4-carboxylic acid
DrugBank Accession Number
DB08375
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 397.429
Monoisotopic: 397.051459995
Chemical Formula
C14H15N5O5S2
Synonyms
  • Pcnotaxime group

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPenicillin-binding protein 1ANot AvailableStreptococcus pneumoniae (strain ATCC BAA-255 / R6)
UBeta-lactamase Toho-1Not AvailableEscherichia coli
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
Medicalerrors
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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
Thiazoles / Heteroaromatic compounds / Ketimines / Isothioureas / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids / Carboximidic acids / Azacyclic compounds
show 4 more
Substituents
Aldehyde / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid / Carboxylic acid derivative / Dialkylthioether
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NRYMPLKBKFIWQC-YVCCLBOHSA-N
InChI
InChI=1S/C14H15N5O5S2/c1-6-4-25-12(18-9(6)13(22)23)7(3-20)16-11(21)10(19-24-2)8-5-26-14(15)17-8/h3,5,7,12H,1,4H2,2H3,(H2,15,17)(H,16,21)(H,22,23)/b19-10-/t7-,12-/m1/s1
IUPAC Name
(2R)-2-[(1R)-1-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoethyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
SMILES
[H][C@@]1(SCC(=C)C(=N1)C(O)=O)[C@H](NC(=O)C(=N/OC)\C1=CSC(N)=N1)C=O

References

General References
Not Available
PubChem Compound
131704308
PubChem Substance
99444846
ChemSpider
26328474
ZINC
ZINC000015605562
PDBe Ligand
CEF
PDB Entries
1cef / 1iyo / 2c5w / 2xd1 / 2zqa / 3ixh / 3m2k / 3sh9 / 3upp / 3vsl
show 14 more

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 Solubility0.0892 mg/mLALOGPS
logP-0.14ALOGPS
logP0.31ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.33 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.64 m3·mol-1ChemAxon
Polarizability37.57 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7941
Blood Brain Barrier-0.8795
Caco-2 permeable-0.635
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8567
P-glycoprotein inhibitor IINon-inhibitor0.9405
Renal organic cation transporterNon-inhibitor0.8971
CYP450 2C9 substrateNon-substrate0.8683
CYP450 2D6 substrateNon-substrate0.824
CYP450 3A4 substrateNon-substrate0.5956
CYP450 1A2 substrateNon-inhibitor0.6771
CYP450 2C9 inhibitorNon-inhibitor0.7044
CYP450 2D6 inhibitorNon-inhibitor0.8898
CYP450 2C19 inhibitorNon-inhibitor0.6694
CYP450 3A4 inhibitorNon-inhibitor0.7209
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8778
Ames testNon AMES toxic0.5623
CarcinogenicityNon-carcinogens0.8573
BiodegradationNot ready biodegradable0.9533
Rat acute toxicity2.4710 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9885
hERG inhibition (predictor II)Non-inhibitor0.9064
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

Drugtargets
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Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Unknown
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
pbpA
Uniprot ID
Q8DR59
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79700.9 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]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
Has strong cefotaxime-hydrolyzing activity.
Gene Name
bla
Uniprot ID
Q47066
Uniprot Name
Beta-lactamase Toho-1
Molecular Weight
31446.6 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]
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 on September 15, 2010 21:31 / Updated on June 12, 2020 16:52