Cloxacillin (CHEM022246)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:25:28 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022246
Identification
Common NameCloxacillin
ClassSmall Molecule
DescriptionA semi-synthetic antibiotic that is a chlorinated derivative of oxacillin.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
(3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillinChEBI
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acidChEBI
CloxacilinaChEBI
CloxacillineChEBI
CloxacillinumChEBI
MCIPCKegg
OrbeninKegg
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanateGenerator
Cloxacillin sodiumHMDB
ChloroxacillinHMDB
TegopenHMDB
Cloxacillin, sodiumHMDB
SyntarpenHMDB
Sodium, cloxacillinHMDB
Sodium cloxacillinHMDB
Chemical FormulaC19H18ClN3O5S
Average Molecular Mass435.881 g/mol
Monoisotopic Mass435.066 g/mol
CAS Registry Number61-72-3
IUPAC Name(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namecloxacillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O
InChI IdentifierInChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
InChI KeyLQOLIRLGBULYKD-JKIFEVAISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Penam
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Beta-lactam
  • Isoxazole
  • Lactam
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.61ALOGPS
logP2.3ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.64 m³·mol⁻¹ChemAxon
Polarizability41.64 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9442300000-e216b172b6089bc0b628Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9201100000-8c62d7bf4821412834e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03fr-0980100000-1acb1c4e617b9afd066cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03fr-0980100000-1acb1c4e617b9afd066cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03fr-0980100000-1acb1c4e617b9afd066cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a5a-0560910000-05dcf2cead0bc1f49482Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-1900000000-a2a9637ec3640b22d439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03g0-1981500000-b5aa89e8243c95661294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mi-1980000000-5959a8cd3ff0d7b69e86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-4940000000-4f39d56cd5b7d76c29f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0092000000-f42335fd75afb22d0d5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0795000000-0f4a7aa6aa6b6709cf76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2920000000-e0da457c632e3e5d44daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1051900000-02e2b7b8281ef5861490Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9250100000-ed86f55f0155aa43591cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001m-9632000000-a8ea4618ee5a92c98b3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0110900000-7f26bb1ece4516994fc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022i-0590300000-7f87c7e79e0101a13c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-1950000000-43f0f287563f32d24bb4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01147
HMDB IDHMDB0015278
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCloxacillin
Chemspider ID5873
ChEBI ID49566
PubChem Compound ID6098
Kegg Compound IDC06923
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16540070
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16853954
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24858821
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25305230
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25582344
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26365730
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27446834
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27889744
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7417768
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8566082