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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014971
Secondary Accession Numbers
  • HMDB14971
Metabolite Identification
Common NameCefaclor
DescriptionCefaclor is only found in individuals that have used or taken this drug. It is a semisynthetic, broad-spectrum antibiotic derivative of cephalexin. [PubChem]Cefaclor, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. It is possible that cefaclor interferes with an autolysin inhibitor.
Structure
Thumb
Synonyms
ValueSource
3-chloro-7-D-(2-phenylglycinamido)-3-Cephem-4-carboxylic acidChEBI
CCLChEBI
Cefaclor anhydrousChEBI
CefaclorumChEBI
CephaclorChEBI
3-chloro-7-D-(2-phenylglycinamido)-3-Cephem-4-carboxylateGenerator
Cefaclor monohydrateMeSH
KeclorMeSH
Lilly 99638MeSH
Anhydrous, cefaclorMeSH
CeclorMeSH
Monohydrate, cefaclorMeSH
Chemical FormulaC15H14ClN3O4S
Average Molecular Weight367.807
Monoisotopic Molecular Weight367.039354348
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
CAS Registry Number53994-73-3
SMILES
[H][C@]12SCC(Cl)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point327 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.21 g/LNot Available
LogP0.4Not 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-72d4be32944ae45064a0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-6920000000-9aa0a1d7b905f4a16720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00dl-1911000000-144d67b80e602cc73566View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fu-0910000000-50ca0c98776044283551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0590000000-34857060856b0cac1c04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00p0-1950000000-9f8a92f4a857c98b63abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0ukc-3920000000-86cb2f866ab059592333View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0fkl-4910000000-c6f6c93efa7b2b3bc3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abc-7900000000-98306dadbeccb72e1ba8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abc-9700000000-f4a33b4825c13beb1024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0900000000-ec391756df89ec0d9544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ab9-0900000000-f3ee64eb3dc5aa901340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0aor-0900000000-c4d5197048a0a6ec18a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0aor-1900000000-5f6c6fcc3196ef576a9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-3900000000-5151a520059ba886f4ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-6900000000-e164f9cd4b1781b2168dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dl-1911000000-144d67b80e602cc73566View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fu-0910000000-50ca0c98776044283551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1912000000-f9a304b4509d8ca89efeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2910000000-53590bb778558be665bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8900000000-d4b848807eae72399204View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-0694000000-648c6b229838bcf7e48bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003i-1922000000-6892cbc88e875d08f188View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055f-9810000000-9e7b4266b0d2c728b78dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00833 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00833 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00833
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID46260
KEGG Compound IDC06877
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefaclor
METLIN IDNot Available
PubChem Compound51039
PDB IDNot Available
ChEBI ID3478
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:1456417 ]
  2. 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. [PubMed:1802903 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Zuccotti G, Dauria E, Torcoletti M, Lodi F, Bernardo L, Riva E: Clinical and pro-host effects of cefaclor in prophylaxis of recurrent otitis media in HIV-infected children. J Int Med Res. 2001 Jul-Aug;29(4):349-54. [PubMed:11675909 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]