Cefaclor (CHEM016609)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:24 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016609
Identification
Common NameCefaclor
ClassSmall Molecule
DescriptionA cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acidChEBI
CCLChEBI
Cefaclor anhydrousChEBI
CefaclorumChEBI
CephaclorChEBI
AlenfralKegg
3-Chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylateGenerator
Cefaclor monohydrateHMDB
KeclorHMDB
Lilly 99638HMDB
Anhydrous, cefaclorHMDB
CeclorHMDB
Monohydrate, cefaclorHMDB
Chemical FormulaC15H14ClN3O4S
Average Molecular Mass367.807 g/mol
Monoisotopic Mass367.039 g/mol
CAS Registry Number53994-73-3
IUPAC Name(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecefaclor
SMILES[H][C@]12SCC(Cl)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
InChI KeyQYIYFLOTGYLRGG-GPCCPHFNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • Cephem
  • Aralkylamine
  • Meta-thiazine
  • Monocyclic benzene moiety
  • Benzenoid
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Vinylogous halide
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Lactam
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Azacycle
  • Chloroalkene
  • Monocarboxylic acid or derivatives
  • Haloalkene
  • Organoheterocyclic compound
  • Thioether
  • Hemithioaminal
  • Vinyl chloride
  • Vinyl halide
  • Dialkylthioether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxide
  • 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 Solubility0.21 g/LALOGPS
logP0.85ALOGPS
logP-2.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.56 m³·mol⁻¹ChemAxon
Polarizability35.11 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-72d4be32944ae45064a0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-6920000000-9aa0a1d7b905f4a16720Spectrum
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 , Positivesplash10-00dl-1911000000-144d67b80e602cc73566Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fu-0910000000-50ca0c98776044283551Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0590000000-34857060856b0cac1c04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00p0-1950000000-9f8a92f4a857c98b63abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0ukc-3920000000-86cb2f866ab059592333Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0fkl-4910000000-c6f6c93efa7b2b3bc3d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abc-7900000000-98306dadbeccb72e1ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abc-9700000000-f4a33b4825c13beb1024Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0900000000-ec391756df89ec0d9544Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ab9-0900000000-f3ee64eb3dc5aa901340Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0aor-0900000000-c4d5197048a0a6ec18a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0aor-1900000000-5f6c6fcc3196ef576a9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-3900000000-5151a520059ba886f4ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-6900000000-e164f9cd4b1781b2168dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dl-1911000000-144d67b80e602cc73566Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fu-0910000000-50ca0c98776044283551Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-000i-0590000000-15051a2093569703db27Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00p0-1950000000-0e536fd1f12aa41f4465Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-066r-3900000000-ba1829fefd11d8f8eaa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1912000000-f9a304b4509d8ca89efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2910000000-53590bb778558be665bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8900000000-d4b848807eae72399204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-0694000000-648c6b229838bcf7e48bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003i-1922000000-6892cbc88e875d08f188Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055f-9810000000-9e7b4266b0d2c728b78dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDDB00833
HMDB IDHMDB0014971
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCefaclor
Chemspider ID46260
ChEBI ID3478
PubChem Compound ID51039
Kegg Compound IDC06877
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10230635
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11963587
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12485718
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15812119
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18969055
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
9. Parra FM, Igea JM, Martin JA, Alonso MD, Lezaun A, Sainz T: Serum sickness-like syndrome associated with cefaclor therapy. Allergy. 1992 Aug;47(4 Pt 2):439-40.
10. Hebert AA, Sigman ES, Levy ML: Serum sickness-like reactions from cefaclor in children. J Am Acad Dermatol. 1991 Nov;25(5 Pt 1):805-8.