You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:01 UTC
Update Date2019-07-23 06:35:08 UTC
HMDB IDHMDB0041852
Secondary Accession Numbers
  • HMDB41852
Metabolite Identification
Common NameCefpirome
DescriptionCefpirome is a fourth-generation cephalosporin. Trade names include Cefrom, Keiten, Broact, Cefir. Cefpirome is considered highly active against Gram-negative bacteria, including Pseudomonas aeruginosa, and Gram-positive bacteria. It is marketed under the brand name of CEFROM by sanofi aventis group india.
Structure
Data?1563863708
Synonyms
ValueSource
HR 810Kegg
CPRKegg
CefirKegg
Cefpirome sulfateHMDB
Cefpirome sulphateHMDB
MetranMeSH
3-((2,3-cyclopenteno-1-Pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylateMeSH
CefromMeSH
Chemical FormulaC22H22N6O5S2
Average Molecular Weight514.577
Monoisotopic Molecular Weight514.109309224
IUPAC Name1-{[(6R,7R)-2-carboxylato-7-{[(2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium
Traditional Namemetran
CAS Registry Number84957-29-9
SMILES
[H][C@]12SCC(C[N+]3=CC=CC4=C3CCC4)=C(N1C(=O)[C@@]2([H])N=C(O)C(=N/OC)\C1=CSC(=N)N1)C([O-])=O
InChI Identifier
InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1
InChI KeyDKOQGJHPHLTOJR-WHRDSVKCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • Pyridine
  • 1,3-thiazol-2-amine
  • Pyridinium
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Azacycle
  • Hemithioaminal
  • Thioether
  • Dialkylthioether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organic salt
  • Organonitrogen compound
  • Organic zwitterion
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP-0.81ALOGPS
logP-4.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)6.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.38 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity154.61 m³·mol⁻¹ChemAxon
Polarizability51.55 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-1932400000-6547b6c109293e8f8d27JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-6895060000-58dbcb11c0c64d95d40bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-db743dc32f22880d8da9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1050190000-2fc4a53db568f4afbec0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007n-9330110000-34acf04b089844c7d19eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000190000-8f5916fff46973753378JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5001190000-e16366a7e786f18376a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-2c0599f22dc8393d24dcJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4586396
KEGG Compound IDC11199
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefpirome
METLIN IDNot Available
PubChem Compound5479539
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available