CHEBI:18165 - isopenicillin N

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name isopenicillin N
ChEBI ID CHEBI:18165
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43447, CHEBI:6036, CHEBI:14472
Supplier Information
Download Molfile XML SDF
Formula C14H21N3O6S
Net Charge 0
Average Mass 359.39916
Monoisotopic Mass 359.11511
InChI InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8+,9-,11+/m0/s1
InChIKey MIFYHUACUWQUKT-GTQWGBSQSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CCC[C@H](N)C(O)=O)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): allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
(via penicillin )
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 isopenicillin N (CHEBI:18165) is a penicillin (CHEBI:17334)
isopenicillin N (CHEBI:18165) is conjugate acid of isopenicillin N(1−) (CHEBI:58399)
Incoming isopenicillin N(1−) (CHEBI:58399) is conjugate base of isopenicillin N (CHEBI:18165)
IUPAC Name
6β-[(5S)-5-amino-5-carboxypentanamido]-2,2-dimethylpenam-3α-carboxylic acid
Synonyms Sources
(2S,5R,6R)-6-[(5S)-5-amino-5-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
Isopenicillin N KEGG COMPOUND
ISOPENICILLIN N PDBeChem
Manual Xrefs Databases
C00000778 KNApSAcK
C05557 KEGG COMPOUND
DB03550 DrugBank
IP1 PDBeChem
View more database links
Registry Number Type Source
5311821 Beilstein Registry Number Beilstein
Last Modified
28 July 2014