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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:21:41 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060450
Secondary Accession Numbers
  • HMDB60450
Metabolite Identification
Common NameCephalosporin C
DescriptionCephalosporin C 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. Cephalosporin C is a very strong basic compound (based on its pKa). Cephalosporin C exists in all living organisms, ranging from bacteria to humans. A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.
Structure
Thumb
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 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
  • Alpha-amino acid
  • D-alpha-amino acid
  • Cephem
  • Tricarboxylic acid or derivatives
  • Meta-thiazine
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Thioether
  • Hemithioaminal
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
Predicted Chromatographic Properties
Spectra
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
MarkerDB IDNot Available
Good Scents 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