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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014419
Secondary Accession Numbers
  • HMDB14419
Metabolite Identification
Common NameCefmetazole
DescriptionCefmetazole is only found in individuals that have used or taken this drug. It is a semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted. [PubChem]The bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Structure
Data?1582753177
Synonyms
ValueSource
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefmetazoloChEBI
CefmetazolumChEBI
CMZKegg
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7S)-7-({[(cyanomethyl)sulphanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7S)-7-({[(cyanomethyl)sulphanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
Monosodium salt, cefmetazoleHMDB
ZefazoneHMDB
CefmetazonHMDB
Pharmacia brand OF cefmetazole sodiumHMDB
Salt, cefmetazole monosodiumHMDB
Cefmetazole monosodium saltHMDB
Cefmetazole sodiumHMDB
Sodium, cefmetazoleHMDB
Chemical FormulaC15H17N7O5S3
Average Molecular Weight471.534
Monoisotopic Molecular Weight471.045328759
IUPAC Name(6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecefmetazole
CAS Registry Number56796-20-4
SMILES
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O
InChI Identifier
InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
InChI KeySNBUBQHDYVFSQF-HIFRSBDPSA-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
  • Aryl thioether
  • Alkylarylthioether
  • Meta-thiazine
  • Azole
  • Beta-lactam
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Azetidine
  • Carboxamide group
  • Lactam
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Carbonitrile
  • Nitrile
  • Organic 1,3-dipolar compound
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.16 g/LNot Available
LogP-2.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.16 g/LALOGPS
logP-0.38ALOGPS
logP-0.65ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area163.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.57 m³·mol⁻¹ChemAxon
Polarizability44.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.50231661259
DarkChem[M-H]-193.67831661259
DeepCCS[M-2H]-225.59130932474
DeepCCS[M+Na]+200.81830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cefmetazole[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O4475.4Standard polar33892256
Cefmetazole[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O3282.5Standard non polar33892256
Cefmetazole[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O3931.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cefmetazole,1TMS,isomer #1CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]213955.6Semi standard non polar33892256
Cefmetazole,1TMS,isomer #2CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CS[C@@H]213851.6Semi standard non polar33892256
Cefmetazole,2TMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]213762.0Semi standard non polar33892256
Cefmetazole,2TMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]213343.4Standard non polar33892256
Cefmetazole,2TMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]216460.3Standard polar33892256
Cefmetazole,1TBDMS,isomer #1CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]214138.5Semi standard non polar33892256
Cefmetazole,1TBDMS,isomer #2CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CS[C@@H]214080.6Semi standard non polar33892256
Cefmetazole,2TBDMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]214166.0Semi standard non polar33892256
Cefmetazole,2TBDMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]213732.6Standard non polar33892256
Cefmetazole,2TBDMS,isomer #1CO[C@@]1(N(C(=O)CSCC#N)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CS[C@@H]216263.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cefmetazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9252300000-3b897b33c8f75fb7d1952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cefmetazole GC-MS (1 TMS) - 70eV, Positivesplash10-05bf-9212320000-890b51c43c3c2ab21ca42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cefmetazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 10V, Positive-QTOFsplash10-00di-1043900000-6c51b4b1826d8fd2c6f02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 20V, Positive-QTOFsplash10-01x3-7940000000-c539600c8e5309da26232016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 40V, Positive-QTOFsplash10-03kl-5393000000-620b60fde9e0798480d52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 10V, Negative-QTOFsplash10-00bc-2434900000-d70717dd74e62de2b0f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 20V, Negative-QTOFsplash10-0a4i-9341200000-9e56fcac14c64926ea082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 40V, Negative-QTOFsplash10-044i-2191000000-2f3da3edb938f355e3832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 10V, Negative-QTOFsplash10-00di-0300900000-77e091905e6148c9a4f82021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 20V, Negative-QTOFsplash10-00xr-4850900000-81fd58ff3fbb9a095c812021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 40V, Negative-QTOFsplash10-014i-9400000000-7442047ce9e5c1ddf3f32021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 10V, Positive-QTOFsplash10-05fr-0008900000-09f33a45a1206aa0b0442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 20V, Positive-QTOFsplash10-00di-4104900000-28beec94cf5d21f8447a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefmetazole 40V, Positive-QTOFsplash10-0006-9102100000-234a13d09fa139832d832021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00274 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00274 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00274
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID38311
KEGG Compound IDC08103
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefmetazole
METLIN IDNot Available
PubChem Compound42008
PDB IDNot Available
ChEBI ID3489
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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. 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 ]