CHEBI:27446 - phenoxymethylpenicillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name phenoxymethylpenicillin
ChEBI ID CHEBI:27446
Definition A penicillin compound having a 6β-(phenoxyacetyl)amino side-chain.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44947, CHEBI:7966, CHEBI:25868
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C16H18N2O5S
Net Charge 0
Average Mass 350.39000
Monoisotopic Mass 350.094
InChI InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChIKey BPLBGHOLXOTWMN-MBNYWOFBSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)COc1ccccc1)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): 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 phenoxymethylpenicillin (CHEBI:27446) is a penicillin (CHEBI:17334)
phenoxymethylpenicillin (CHEBI:27446) is conjugate acid of phenoxymethylpenicillin(1−) (CHEBI:51355)
Incoming phenoxymethylpenicillin(1−) (CHEBI:51355) is conjugate base of phenoxymethylpenicillin (CHEBI:27446)
phenoxymethylpenicillanyl group (CHEBI:53706) is substituent group from phenoxymethylpenicillin (CHEBI:27446)
phenoxymethylpenicilloyl group (CHEBI:53703) is substituent group from phenoxymethylpenicillin (CHEBI:27446)
IUPAC Names
2,2-dimethyl-6β-[(phenoxyacetyl)amino]penam-3α-carboxylic acid
3,3-dimethyl-6β-[(phenoxyacetyl)amino]penam-2α-carboxylic acid (PIN)
INNs Sources
fenoximetilpenicilina ChemIDplus
phenoxymethylpenicillin KEGG DRUG
phénoxyméthylpénicilline ChemIDplus
phenoxymethylpenicillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1- AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID PDBeChem
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6-phenoxyacetamidopenicillanic acid ChemIDplus
Oracillin ChemIDplus
penicillin phenoxymethyl ChemIDplus
Penicillin V KEGG COMPOUND
phenoxomethylpenicillin ChEBI
phenoxymethylenepenicillinic acid ChemIDplus
PV ChEBI
Brand Names Sources
Fenospen ChemIDplus
V-Cillin KEGG DRUG
Database Links Databases
2083 DrugCentral
C08126 KEGG COMPOUND
D05411 KEGG DRUG
DB00417 DrugBank
Phenoxymethylpenicillin Wikipedia
PNV PDBeChem
View more database links
Registry Numbers Types Sources
87-08-1 CAS Registry Number ChemIDplus
96259 Beilstein Registry Number Beilstein
96259 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10930630 PubMed citation Europe PMC
12569987 PubMed citation Europe PMC
13377278 PubMed citation Europe PMC
14687482 PubMed citation Europe PMC
16033609 PubMed citation Europe PMC
19357666 PubMed citation Europe PMC
19496253 PubMed citation Europe PMC
21148688 PubMed citation Europe PMC
22763423 PubMed citation Europe PMC
23732051 PubMed citation Europe PMC
26986755 PubMed citation Europe PMC
27731424 PubMed citation Europe PMC
8566082 PubMed citation Europe PMC
Last Modified
22 February 2017