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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, also known as HR 810 or cefrom, belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Cefpirome is a drug. Cefpirome is a very strong basic compound (based on its pKa). A fourth-generation cephalosporin antibiotic having 6,7-dihydro-5H-cyclopentapyridinium-1-ylmethyl and amino side groups located at positions 3 and 7 respectively.
Structure
Data?1563863708
Synonyms
ValueSource
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateChEBI
CefpiromaChEBI
CefpiromumChEBI
CefromChEBI
HR 810ChEBI
CPRKegg
CefirKegg
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
Cefpirome sulfateHMDB
Cefpirome sulphateHMDB
MetranHMDB
3-((2,3-Cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylateHMDB
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
Description belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub ClassNot Available
Direct ParentBenzopyrans
Alternative Parents
Substituents
  • Benzopyran
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-1932400000-6547b6c109293e8f8d27Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-6895060000-58dbcb11c0c64d95d40bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-db743dc32f22880d8da9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1050190000-2fc4a53db568f4afbec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007n-9330110000-34acf04b089844c7d19eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000190000-8f5916fff46973753378Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5001190000-e16366a7e786f18376a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-2c0599f22dc8393d24dcSpectrum
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 IDDB13682
Phenol Explorer Compound IDNot Available
FooDB 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 ID3503
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available