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CHEBI:18208 - benzylpenicillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name benzylpenicillin
ChEBI ID CHEBI:18208
Definition A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25866, CHEBI:45073, CHEBI:7962, CHEBI:14743
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Formula C16H18N2O4S
Net Charge 0
Average Mass 334.392
Monoisotopic Mass 334.099
InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
SMILES N12C([C@H]([C@]1(SC([C@@H]2C(O)=O)(C)C)[H])NC(CC3=CC=CC=C3)=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): antibacterial drug
A drug used to treat or prevent bacterial infections.
epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
allergen
A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
(via penicillin allergen )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing benzylpenicillin (CHEBI:18208) has role antibacterial drug (CHEBI:36047)
benzylpenicillin (CHEBI:18208) has role epitope (CHEBI:53000)
benzylpenicillin (CHEBI:18208) is a penicillin (CHEBI:17334)
benzylpenicillin (CHEBI:18208) is a penicillin allergen (CHEBI:88187)
benzylpenicillin (CHEBI:18208) is conjugate acid of benzylpenicillin(1−) (CHEBI:51354)
Incoming benzylpenicilloyl polylysine (CHEBI:59297) has functional parent benzylpenicillin (CHEBI:18208)
benzylpenicilloyl-benzylamine (CHEBI:42719) has functional parent benzylpenicillin (CHEBI:18208)
benzylpenicilloyl-butylamine (CHEBI:55472) has functional parent benzylpenicillin (CHEBI:18208)
benzylpenicilloyl-cysteine (CHEBI:60178) has functional parent benzylpenicillin (CHEBI:18208)
penamecillin (CHEBI:131733) has functional parent benzylpenicillin (CHEBI:18208)
benzylpenicillin(1−) (CHEBI:51354) is conjugate base of benzylpenicillin (CHEBI:18208)
benzylpenicillanyl group (CHEBI:53600) is substituent group from benzylpenicillin (CHEBI:18208)
benzylpenicilloyl group (CHEBI:53702) is substituent group from benzylpenicillin (CHEBI:18208)
IUPAC Name
2,2-dimethyl-6β-(phenylacetamido)penam-3α-carboxylic acid
INNs Sources
bencilpenicilina ChemIDplus
benzylpenicillin KEGG DRUG
benzylpénicilline ChemIDplus
benzylpenicillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid ChEBI
6-(2-phenylacetamido)penicillanic acid ChemIDplus
bensylpenicillin ChEBI
benzyl benicillin ChEBI
Benzylpenicillin KEGG COMPOUND
benzylpenicillinic acid ChemIDplus
free penicillin II ChemIDplus
Penicillin G KEGG COMPOUND
PENICILLIN G PDBeChem
PG ChEBI
Database Links Databases
Benzylpenicillin Wikipedia
C05551 KEGG COMPOUND
D02336 KEGG DRUG
DB01053 DrugBank
HMDB15186 HMDB
LSM-3229 LINCS
PNN PDBeChem
US3024169 Patent
View more database links
Registry Numbers Types Sources
44740 Beilstein Registry Number Beilstein
44740 Reaxys Registry Number Reaxys
61-33-6 CAS Registry Number KEGG COMPOUND
61-33-6 CAS Registry Number ChemIDplus
781913 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
10930630 PubMed citation Europe PMC
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7716788 PubMed citation Europe PMC
Last Modified
14 April 2016