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 Date2013-05-17 01:21:41 UTC
Update Date2019-07-23 07:14:22 UTC
HMDB IDHMDB0060450
Secondary Accession Numbers
  • HMDB60450
Metabolite Identification
Common NameCephalosporin C
DescriptionCephalosporin C belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Cephalosporin C is a very strong basic compound (based on its pKa). Cephalosporin C is an antibiotic of the cephalosporin class. Cephalosporin C exists in all living organisms, ranging from bacteria to humans. It was isolated from fungi of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs.
Structure
Data?1563866062
Synonyms
ValueSource
7-(5-Amino-5-carboxyvaleramido)cephalosporanic acidChEBI
7-(5-Amino-5-carboxyvaleramido)cephalosporanateGenerator
Cephalosporin C hydrochlorideHMDB
Cephalosporin C, monosodium salt, (6R-(6alpha,7beta))-isomerHMDB
Cephalosporin C, sodium saltHMDB
Cephalosporin C, sodium salt, (6R-(6alpha,7beta))-isomerHMDB
Cephalosporin C, monosodium saltHMDB
Cephalosporin C, monozinc saltHMDB
Cephalosporin C, potassium saltHMDB
Cephalosporin C, potassium salt, (6R-(6alpha,7beta(s*)))-isomerHMDB
Cephalosporin C, zinc saltHMDB
Chemical FormulaC16H21N3O8S
Average Molecular Weight415.418
Monoisotopic Molecular Weight415.104935353
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecephalosporin C
CAS Registry NumberNot Available
SMILES
CC(=O)OCC1=C(N2[C@H](SC1)[C@H](N=C(O)CCC[C@@H](N)C(O)=O)C2=O)C(O)=O
InChI Identifier
InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
InChI KeyHOKIDJSKDBPKTQ-GLXFQSAKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Organic phosphoric acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Alkyl chloride
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

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 Solubility0.39 g/LALOGPS
logP-2.1ALOGPS
logP-3.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area179.82 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity95.95 m³·mol⁻¹ChemAxon
Polarizability40.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9328000000-51dcafd0526ede8e8796Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014l-8430397000-0aba7bced0b47e901395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06di-2197100000-4118be5ec26b8da09d47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06di-2493000000-9bcf4178007a4d4ab3f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-9452000000-4bf4e95dcac42986000cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1924100000-65d25bb2aa874f7ccab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052g-7894000000-118d3e4d302e76adc5d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9210000000-0b47d4a8a6fca75ca262Spectrum
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 IDDB03313
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00916
BioCyc IDCSC
BiGG IDNot Available
Wikipedia LinkCephalosporin_C
METLIN IDNot Available
PubChem Compound65536
PDB IDNot Available
ChEBI ID15776
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
Cephalosporin C + Water + Oxygen → (7R)-7-(5-Carboxy-5-oxopentanoyl)aminocephalosporinate + Ammonia + Hydrogen peroxidedetails