(2R)-2-[(1R)-1-{[(2S)-2-Carboxy-2-(4-hydroxyphenyl)acetyl]amino}-1-methoxy-2-oxoethyl]-5-methylene-5,6-dihydro-2H-1,3-oxazine-4-carboxylic acid

Identification

Generic Name
(2R)-2-[(1R)-1-{[(2S)-2-Carboxy-2-(4-hydroxyphenyl)acetyl]amino}-1-methoxy-2-oxoethyl]-5-methylene-5,6-dihydro-2H-1,3-oxazine-4-carboxylic acid
DrugBank Accession Number
DB02588
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 406.3435
Monoisotopic: 406.101230184
Chemical Formula
C18H18N2O9
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GOYCBKVVHGALFQ-RZAIGCCYSA-N
InChI
InChI=1S/C18H18N2O9/c1-9-7-29-17(19-13(9)16(26)27)18(8-21,28-2)20-14(23)12(15(24)25)10-3-5-11(22)6-4-10/h3-6,8,12,17,22H,1,7H2,2H3,(H,20,23)(H,24,25)(H,26,27)/t12-,17+,18-/m0/s1
IUPAC Name
(2R)-2-{1-[(2S)-2-carboxy-2-(4-hydroxyphenyl)acetamido]-1-methoxy-2-oxoethyl}-5-methylidene-5,6-dihydro-2H-1,3-oxazine-4-carboxylic acid
SMILES
COC(NC(=O)[C@@H](C(O)=O)C1=CC=C(O)C=C1)(C=O)[C@H]1OCC(=C)C(=N1)C(O)=O

References

General References
Not Available
PubChem Compound
131704211
PubChem Substance
46506599
ChemSpider
26328061
ZINC
ZINC000015529397
PDBe Ligand
MOX
PDB Entries
1fco / 1i5q

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 Solubility0.225 mg/mLALOGPS
logP1.11ALOGPS
logP1.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area171.82 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.83 m3·mol-1ChemAxon
Polarizability37.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8196
Blood Brain Barrier-1.0
Caco-2 permeable-0.6744
P-glycoprotein substrateSubstrate0.8161
P-glycoprotein inhibitor INon-inhibitor0.6713
P-glycoprotein inhibitor IINon-inhibitor0.6452
Renal organic cation transporterNon-inhibitor0.9366
CYP450 2C9 substrateNon-substrate0.8483
CYP450 2D6 substrateNon-substrate0.8706
CYP450 3A4 substrateSubstrate0.6358
CYP450 1A2 substrateNon-inhibitor0.807
CYP450 2C9 inhibitorNon-inhibitor0.8242
CYP450 2D6 inhibitorNon-inhibitor0.8963
CYP450 2C19 inhibitorNon-inhibitor0.7774
CYP450 3A4 inhibitorNon-inhibitor0.7485
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7646
Ames testNon AMES toxic0.5666
CarcinogenicityNon-carcinogens0.9284
BiodegradationNot ready biodegradable0.9854
Rat acute toxicity2.3783 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9962
hERG inhibition (predictor II)Non-inhibitor0.8606
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 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at August 01, 2020 13:44