Flucloxacillin (CHEM022085)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:19:34 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022085
Identification
Common NameFlucloxacillin
ClassSmall Molecule
DescriptionAntibiotic analog of [cloxacillin].
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillinChEBI
FloxacillinChEBI
FloxapenChEBI
FlucloxacilinaChEBI
FlucloxacillineChEBI
FlucloxacillinumChEBI
MFIPCKegg
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
Flucloxacillin-sodiumHMDB
FluorochloroxacillinHMDB
Chemical FormulaC19H17ClFN3O5S
Average Molecular Mass453.872 g/mol
Monoisotopic Mass453.056 g/mol
CAS Registry Number5250-39-5
IUPAC Name(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameflucloxacillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O
InChI IdentifierInChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
InChI KeyUIOFUWFRIANQPC-JKIFEVAISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as mitomycins. These are polycyclic compounds with a structure based on an aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolequinones
Direct ParentMitomycins
Alternative Parents
Substituents
  • Mitomycin
  • Indole
  • Quinone
  • Pyrrolizine
  • 1,4-diazinane
  • Piperazine
  • Pyrrolidine
  • Vinylogous amide
  • Pyrroline
  • Ketone
  • Aziridine
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Azacycle
  • Secondary amine
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 Solubility0.054 g/LALOGPS
logP2.69ALOGPS
logP2.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.85 m³·mol⁻¹ChemAxon
Polarizability41.69 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-9342300000-7f180b75f0b193e6a2bfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9101010000-2499cba418eeed4ea1e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ika-1980600000-c09913017680462d6167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1890100000-189280e6a5ebaeff7bcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-3930000000-082278659456539aa269Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029100000-f63d442cb388e6e6a1feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0179100000-cc81474beec5e49ab711Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2943000000-01ada58e630c1108bd3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0110900000-0d61735c2eb814141c04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2i-0590300000-b1e7d7edf8865b92c33aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2590000000-21280c81506029576bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0030900000-0ee6d1f66c3759d652feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-4190100000-fc1930da2cf7aa599457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9170000000-0fa52b5f4e2c50ce52adSpectrum
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 IDDB00301
HMDB IDHMDB0014446
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlucloxacillin
Chemspider ID20037
ChEBI ID5098
PubChem Compound ID21319
Kegg Compound IDC11748
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15773973
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23032409
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23542420
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25998949
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=5481218