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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015270
Secondary Accession Numbers
  • HMDB0030451
  • HMDB15270
  • HMDB30451
Metabolite Identification
Common NameCephapirin
DescriptionCephapirin is an injectable, first-generation cephalosporin antibiotic that has a wide spectrum of activity against gram-positive and gram-negative organisms. The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cephapirin is more resistant to beta-lactamases than the penicillins, and therefore is effective against staphylococci, with the exception of methicillin-resistant staphylococci. Cephapirin is FDA approved for use in food-producing animals, especially dairy cattle. Cephapirin is used for the treatment of mastitis in cows. Production for use in humans has been discontinued in the United States. It is marketed under the trade name Cefadyl.
Structure
Data?1582753277
Synonyms
ValueSource
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefapirinChEBI
CefapirinaChEBI
CefapirineChEBI
CefapirinumChEBI
CefaprinChEBI
CephapirineChEBI
CEPRChEBI
MetricureKegg
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
CefadylHMDB
Monosodium salt, cephapirinHMDB
Salt, cephapirin monosodiumHMDB
BL p 1322HMDB
Bristol-myers brand OF cephapirin sodiumHMDB
Cephapirin, sodiumHMDB
Apothecon brand OF cephapirin sodiumHMDB
Cephapirin sodiumHMDB
CéfalojectHMDB
Sodium cephapirinHMDB
BL-p 1322HMDB
BrisfirinaHMDB
Bristol-myers squibb brand OF cephapirin sodiumHMDB
Cephapirin monosodium saltHMDB
CephapirinKEGG
Chemical FormulaC17H17N3O6S2
Average Molecular Weight423.463
Monoisotopic Molecular Weight423.055876671
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional NameCEPR
CAS Registry Number21593-23-7
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O
InChI Identifier
InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
InChI KeyUQLLWWBDSUHNEB-CZUORRHYSA-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
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Heteroaromatic compound
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Azetidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Dialkylthioether
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Hemithioaminal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP-0.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available179.888http://allccs.zhulab.cn/database/detail?ID=AllCCS00001282
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP0.18ALOGPS
logP-2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area125.9 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.43 m³·mol⁻¹ChemAxon
Polarizability40.63 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]+194.08231661259
DarkChem[M-H]-181.43131661259
DeepCCS[M-2H]-226.20130932474
DeepCCS[M+Na]+201.42930932474
AllCCS[M+H]+190.632859911
AllCCS[M+H-H2O]+188.532859911
AllCCS[M+NH4]+192.632859911
AllCCS[M+Na]+193.232859911
AllCCS[M-H]-186.132859911
AllCCS[M+Na-2H]-186.332859911
AllCCS[M+HCOO]-186.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cephapirin[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O4778.1Standard polar33892256
Cephapirin[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O2715.2Standard non polar33892256
Cephapirin[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O3557.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cephapirin,1TMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](NC(=O)CSC3=CC=NC=C3)[C@H]2SC13370.2Semi standard non polar33892256
Cephapirin,1TMS,isomer #2CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C)[C@H]2SC13295.9Semi standard non polar33892256
Cephapirin,2TMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C)[C@H]2SC13197.4Semi standard non polar33892256
Cephapirin,2TMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C)[C@H]2SC12999.1Standard non polar33892256
Cephapirin,2TMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C)[C@H]2SC14747.4Standard polar33892256
Cephapirin,1TBDMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](NC(=O)CSC3=CC=NC=C3)[C@H]2SC13542.4Semi standard non polar33892256
Cephapirin,1TBDMS,isomer #2CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC13487.8Semi standard non polar33892256
Cephapirin,2TBDMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC13590.8Semi standard non polar33892256
Cephapirin,2TBDMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC13377.3Standard non polar33892256
Cephapirin,2TBDMS,isomer #1CC(=O)OCC1=C(C(=O)O[Si](C)(C)C(C)(C)C)N2C(=O)[C@@H](N(C(=O)CSC3=CC=NC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC14774.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cephapirin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9373100000-e3d19d32bd32937d2df32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cephapirin GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9221200000-5b079bfce3f72569ddd82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cephapirin 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 - Cephapirin 10V, Positive-QTOFsplash10-0ck9-1193200000-dbd8b4f9cdd95af96beb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 20V, Positive-QTOFsplash10-0aor-3493000000-9715d40cfca13766b6462016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 40V, Positive-QTOFsplash10-0903-9740000000-3730a9b0ee7ce8523e452016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 10V, Negative-QTOFsplash10-0bt9-2693100000-30db005d7cf1f9280b9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 20V, Negative-QTOFsplash10-08fr-5982000000-04fa910b005391b048912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 40V, Negative-QTOFsplash10-03dl-9470000000-f3f678bd4350e63bc6bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 10V, Negative-QTOFsplash10-00di-0018900000-9afce8e794a582cdcf942021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 20V, Negative-QTOFsplash10-03di-4932100000-cfcc654bebe5ca1a549a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 40V, Negative-QTOFsplash10-03dl-9610000000-a89d7ebde3d9ad8d7ac22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 10V, Positive-QTOFsplash10-0229-0008900000-d203511cd0ef491771f22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 20V, Positive-QTOFsplash10-03di-1954100000-54810442e303dd9f9e412021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cephapirin 40V, Positive-QTOFsplash10-03l0-3920000000-099e86960b6137b688722021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01139 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01139 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01139
Phenol Explorer Compound IDNot Available
FooDB IDFDB002317
KNApSAcK IDNot Available
Chemspider ID28486
KEGG Compound IDC06896
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCephapirin
METLIN IDNot Available
PubChem Compound30699
PDB IDNot Available
ChEBI ID554446
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 References
  1. Simonet M, Herrmann JL, Gehanno P, Veron M: [Activity of cefapirin against bacterial strains isolated from acute otitis media in children]. Pathol Biol (Paris). 1990 May;38(5):352-4. [PubMed:2114604 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .