7-(2-Amino-2-Phenyl-Acetylamino)-3-Chloro-8-Oxo-1-Aza-Bicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid
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Identification
- Generic Name
- 7-(2-Amino-2-Phenyl-Acetylamino)-3-Chloro-8-Oxo-1-Aza-Bicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid
- DrugBank Accession Number
- DB04293
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 349.769
Monoisotopic: 349.082933722 - Chemical Formula
- C16H16ClN3O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBeta-lactamase Not Available Escherichia 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 carbacephems. These are a new class of beta-lactam antibiotics similar in structure to the cephalosporins. They differ from cephalosporins, however, in the substitution of a sulfur atom in the dihydrothiazine ring with a methylene group to form a tetrahydropyridine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Carbacephems
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Tetrahydropyridines / Aralkylamines / Vinylogous halides / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines show 11 more
- Substituents
- Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- JAPHQRWPEGVNBT-IJLUTSLNSA-N
- InChI
- InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- N[C@@H](C(=O)N[C@@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 12897341
- PubChem Substance
- 46507072
- ChemSpider
- 26330257
- ChEMBL
- CHEMBL3545874
- PDBe Ligand
- LOR
Clinical Trials
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
Property Value Source Water Solubility 0.325 mg/mL ALOGPS logP 0.55 ALOGPS logP -2.4 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 2.93 Chemaxon pKa (Strongest Basic) 7.23 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 112.73 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 86.64 m3·mol-1 Chemaxon Polarizability 34.15 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6242 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.8958 P-glycoprotein substrate Substrate 0.7255 P-glycoprotein inhibitor I Non-inhibitor 0.89 P-glycoprotein inhibitor II Non-inhibitor 0.9848 Renal organic cation transporter Non-inhibitor 0.8905 CYP450 2C9 substrate Non-substrate 0.8338 CYP450 2D6 substrate Non-substrate 0.8339 CYP450 3A4 substrate Substrate 0.5199 CYP450 1A2 substrate Non-inhibitor 0.82 CYP450 2C9 inhibitor Non-inhibitor 0.8491 CYP450 2D6 inhibitor Non-inhibitor 0.888 CYP450 2C19 inhibitor Non-inhibitor 0.7748 CYP450 3A4 inhibitor Non-inhibitor 0.6813 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9341 Ames test Non AMES toxic 0.6788 Carcinogenicity Non-carcinogens 0.929 Biodegradation Not ready biodegradable 0.9959 Rat acute toxicity 2.1829 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9752 hERG inhibition (predictor II) Non-inhibitor 0.8654
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-1900000000-77f09ecdde38884739b9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0fsi-0229000000-f893420c11cdd15c6f8b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-1519000000-32b95926026bbcd17789 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-9700000000-a697ffbb198a9c0886d8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9301000000-f40ca6db6c505150a883 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-4921000000-9939323d7b40c2339873 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9500000000-b60c7ac90e8f37bda538 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.66183 predictedDeepCCS 1.0 (2019) [M+H]+ 183.05739 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.00719 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsBeta-lactamase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52