CHEBI:7447 - nafcillin

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ChEBI Name nafcillin
ChEBI ID CHEBI:7447
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44256
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Formula C21H22N2O5S
Net Charge 0
Average Mass 414.47500
Monoisotopic Mass 414.125
InChI InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1
InChIKey GPXLMGHLHQJAGZ-JTDSTZFVSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)c1c(OCC)ccc2ccccc12)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.
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 nafcillin (CHEBI:7447) has role antibacterial drug (CHEBI:36047)
nafcillin (CHEBI:7447) is a penicillin (CHEBI:17334)
nafcillin (CHEBI:7447) is conjugate acid of nafcillin(1−) (CHEBI:51918)
Incoming nafcillin(1−) (CHEBI:51918) is conjugate base of nafcillin (CHEBI:7447)
IUPAC Name
6β-(2-ethoxynaphthalene-1-carboxamido)-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
nafcilina DrugBank
nafcillin ChemIDplus
nafcilline DrugBank
nafcillinum DrugBank
Synonyms Sources
(2-ethoxy-1-naphthalenyl)penicillin ChemIDplus
(2-ethoxy-1-naphthyl)penicillin ChemIDplus
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6-(2-ethoxy-1-naphthamido)penicillanic acid Patent
naphcillin ChemIDplus
Database Links Databases
1869 DrugCentral
C07250 KEGG COMPOUND
D08242 KEGG DRUG
DB00607 DrugBank
GB880400 Patent
LSM-2402 LINCS
Nafcillin Wikipedia
US3157639 Patent
US3506645 Patent
View more database links
Registry Numbers Types Sources
147-52-4 CAS Registry Number KEGG COMPOUND
147-52-4 CAS Registry Number ChemIDplus
5405727 Beilstein Registry Number Beilstein
Last Modified
22 February 2017