CHEBI:51207 - penicillin O

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ChEBI Name penicillin O
ChEBI ID CHEBI:51207
Definition A penicillin where the side-chain N-acyl group is specified as allylmercaptoacetyl. Antibiotic isolated from Penicillium chrysogenum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C13H18N2O4S2
Net Charge 0
Average Mass 330.42510
Monoisotopic Mass 330.071
InChI InChI=1S/C13H18N2O4S2/c1-4-5-20-6-7(16)14-8-10(17)15-9(12(18)19)13(2,3)21-11(8)15/h4,8-9,11H,1,5-6H2,2-3H3,(H,14,16)(H,18,19)/t8-,9+,11-/m1/s1
InChIKey QULKGELYPOJSLP-WCABBAIRSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CSCC=C)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing penicillin O (CHEBI:51207) has role Penicillium metabolite (CHEBI:76964)
penicillin O (CHEBI:51207) is a penicillin (CHEBI:17334)
Incoming allylmercaptomethylpenicilloyl group (CHEBI:63404) has functional parent penicillin O (CHEBI:51207)
IUPAC Name
6β-[(prop-2-en-1-ylsulfanyl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
almecilina ChemIDplus
almecillin ChemIDplus
almecilline ChemIDplus
almecillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(prop-2-en-1-ylsulfanyl)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
(2S,5R,6R)-6-{[(allylsulfanyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
allylmercaptomethylpenicillin ChemIDplus
allylmercaptomethylpenicillinic acid ChemIDplus
allylthiomethylpenicillin ChemIDplus
penicillin AT ChemIDplus
Manual Xrefs Databases
3422 DrugCentral
C17405 KEGG COMPOUND
US2528175 Patent
US2623876 Patent
View more database links
Registry Numbers Types Sources
44307 Beilstein Registry Number Beilstein
44307 Reaxys Registry Number Reaxys
87-09-2 CAS Registry Number KEGG COMPOUND
87-09-2 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
13761469 PubMed citation Europe PMC
Last Modified
22 February 2017