CHEBI:15776 - cephalosporin C

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ChEBI Name cephalosporin C
ChEBI ID CHEBI:15776
Definition A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N6-L-lysino group at position 7.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3539, CHEBI:13953, CHEBI:23065
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Formula C16H21N3O8S
Net Charge 0
Average Mass 415.41800
Monoisotopic Mass 415.105
InChI 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
InChIKey HOKIDJSKDBPKTQ-GLXFQSAKSA-N
SMILES [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CCC[C@@H](N)C(O)=O)C(O)=O
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cephalosporin C (CHEBI:15776) has functional parent cephalosporanic acid (CHEBI:23064)
cephalosporin C (CHEBI:15776) has role fungal metabolite (CHEBI:76946)
cephalosporin C (CHEBI:15776) is a cephalosporin (CHEBI:23066)
cephalosporin C (CHEBI:15776) is conjugate acid of cephalosporin C(1−) (CHEBI:57511)
Incoming deacetoxycephalosporin C (CHEBI:18229) has functional parent cephalosporin C (CHEBI:15776)
cephalosporin C(1−) (CHEBI:57511) is conjugate base of cephalosporin C (CHEBI:15776)
IUPAC Name
(6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxypentanoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms Sources
7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid ChemIDplus
Cephalosporin C KEGG COMPOUND
Database Links Databases
C00916 KEGG COMPOUND
Cephalosporin_C Wikipedia
CSC PDBeChem
CSC MetaCyc
DB03313 DrugBank
HMDB60450 HMDB
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Registry Numbers Types Sources
61-24-5 CAS Registry Number KEGG COMPOUND
61-24-5 CAS Registry Number ChemIDplus
65348 Reaxys Registry Number Reaxys
65348 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
13315229 PubMed citation Europe PMC
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20171092 PubMed citation Europe PMC
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Last Modified
24 November 2014