CHEBI:8232 - piperacillin

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ChEBI Name piperacillin
ChEBI ID CHEBI:8232
Definition A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:475140, CHEBI:505944, CHEBI:472443
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Formula C23H27N5O7S
Net Charge 0
Average Mass 517.55500
Monoisotopic Mass 517.16312
InChI InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)c1ccccc1)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): antibacterial drug
A drug used to treat or prevent bacterial infections.
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 )
(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.
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ChEBI Ontology
Outgoing piperacillin (CHEBI:8232) has role antibacterial drug (CHEBI:36047)
piperacillin (CHEBI:8232) is a penicillin (CHEBI:17334)
piperacillin (CHEBI:8232) is a penicillin allergen (CHEBI:88187)
piperacillin (CHEBI:8232) is conjugate acid of piperacillin(1−) (CHEBI:52433)
Incoming piperacilloyl-L-lysine (CHEBI:139364) has functional parent piperacillin (CHEBI:8232)
piperacillin(1−) (CHEBI:52433) is conjugate base of piperacillin (CHEBI:8232)
piperacilloyl group (CHEBI:139370) is substituent group from piperacillin (CHEBI:8232)
IUPAC Name
6β-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3α-carboxylic acid
INN Source
piperacillin KEGG DRUG
Synonyms Sources
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
Piperacillin KEGG COMPOUND
Piperacillin anhydrous KEGG COMPOUND
Manual Xrefs Databases
2187 DrugCentral
C14034 KEGG COMPOUND
D08380 KEGG DRUG
DB00319 DrugBank
DE2519400 Patent
LSM-5924 LINCS
Piperacillin Wikipedia
US4087424 Patent
View more database links
Registry Numbers Types Sources
6081140 Reaxys Registry Number Reaxys
61477-96-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1701026 PubMed citation Europe PMC
17116662 PubMed citation ChEMBL
17158942 PubMed citation ChEMBL
17851079 PubMed citation ChEMBL
25998949 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
29148816 PubMed citation Europe PMC
7486906 PubMed citation Europe PMC
Last Modified
15 March 2018