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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:01 UTC
Update Date2022-03-07 02:57:13 UTC
HMDB IDHMDB0041852
Secondary Accession Numbers
  • HMDB41852
Metabolite Identification
Common NameCefpirome
DescriptionCefpirome, also known as HR 810 or cefpiromum, belongs to the class of organic compounds known as cephalosporins. Cephalosporins 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. Based on a literature review a small amount of articles have been published on Cefpirome.
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
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
CPRHMDB
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 cephalosporins. Cephalosporins 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
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-239.16430932474
DeepCCS[M+Na]+214.04130932474
AllCCS[M+H]+210.932859911
AllCCS[M+H-H2O]+209.332859911
AllCCS[M+NH4]+212.232859911
AllCCS[M+Na]+212.632859911
AllCCS[M-H]-199.132859911
AllCCS[M+Na-2H]-199.632859911
AllCCS[M+HCOO]-200.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cefpirome[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-])=O5618.6Standard polar33892256
Cefpirome[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-])=O4113.6Standard non polar33892256
Cefpirome[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-])=O4539.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cefpirome,1TMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N)[NH]14191.4Semi standard non polar33892256
Cefpirome,1TMS,isomer #2CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C)[NH]14190.0Semi standard non polar33892256
Cefpirome,1TMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N)N1[Si](C)(C)C4217.3Semi standard non polar33892256
Cefpirome,2TMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N[Si](C)(C)C)[NH]14112.7Semi standard non polar33892256
Cefpirome,2TMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N[Si](C)(C)C)[NH]13807.4Standard non polar33892256
Cefpirome,2TMS,isomer #2CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N)N1[Si](C)(C)C4201.8Semi standard non polar33892256
Cefpirome,2TMS,isomer #2CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N)N1[Si](C)(C)C3902.3Standard non polar33892256
Cefpirome,2TMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C)N1[Si](C)(C)C4127.6Semi standard non polar33892256
Cefpirome,2TMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C)N1[Si](C)(C)C3848.4Standard non polar33892256
Cefpirome,3TMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N[Si](C)(C)C)N1[Si](C)(C)C4095.2Semi standard non polar33892256
Cefpirome,3TMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C)C1=CSC(=N[Si](C)(C)C)N1[Si](C)(C)C3846.6Standard non polar33892256
Cefpirome,1TBDMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N)[NH]14328.8Semi standard non polar33892256
Cefpirome,1TBDMS,isomer #2CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C(C)(C)C)[NH]14333.7Semi standard non polar33892256
Cefpirome,1TBDMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N)N1[Si](C)(C)C(C)(C)C4347.0Semi standard non polar33892256
Cefpirome,2TBDMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N[Si](C)(C)C(C)(C)C)[NH]14359.5Semi standard non polar33892256
Cefpirome,2TBDMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N[Si](C)(C)C(C)(C)C)[NH]14203.8Standard non polar33892256
Cefpirome,2TBDMS,isomer #2CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N)N1[Si](C)(C)C(C)(C)C4428.5Semi standard non polar33892256
Cefpirome,2TBDMS,isomer #2CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N)N1[Si](C)(C)C(C)(C)C4260.5Standard non polar33892256
Cefpirome,2TBDMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C4388.4Semi standard non polar33892256
Cefpirome,2TBDMS,isomer #3CO/N=C(\C(O)=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)C1=CSC(=N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C4288.4Standard non polar33892256
Cefpirome,3TBDMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C4477.2Semi standard non polar33892256
Cefpirome,3TBDMS,isomer #1CO/N=C(\C(=N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3=CC=CC4=C3CCC4)CS[C@H]12)O[Si](C)(C)C(C)(C)C)C1=CSC(=N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C4402.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cefpirome GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-1932400000-6547b6c109293e8f8d272017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cefpirome GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-6895060000-58dbcb11c0c64d95d40b2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 10V, Positive-QTOFsplash10-014i-0000090000-db743dc32f22880d8da92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 20V, Positive-QTOFsplash10-014i-1050190000-2fc4a53db568f4afbec02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 40V, Positive-QTOFsplash10-007n-9330110000-34acf04b089844c7d19e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 10V, Negative-QTOFsplash10-03di-1000190000-8f5916fff469737533782017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 20V, Negative-QTOFsplash10-03di-5001190000-e16366a7e786f18376a02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 40V, Negative-QTOFsplash10-0a4l-9000000000-2c0599f22dc8393d24dc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 10V, Negative-QTOFsplash10-01ri-0010920000-22e5269f577b1337f0e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 20V, Negative-QTOFsplash10-00di-2972430000-47187a50703cc4b855f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 40V, Negative-QTOFsplash10-06dj-7900100000-c7f1f12668cbc3056fe52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 10V, Positive-QTOFsplash10-014i-0411190000-78a478844ba21ce19d3e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 20V, Positive-QTOFsplash10-01e9-0986550000-512f3743a0e32e70ae342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cefpirome 40V, Positive-QTOFsplash10-053u-3900100000-10484237bcb3db025b6c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available