CHEBI:6827 - methicillin

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ChEBI Name methicillin
Definition A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H20N2O6S
Net Charge 0
Average Mass 380.41500
Monoisotopic Mass 380.10421
InChI InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)c1c(OC)cccc1OC)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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methicillin (CHEBI:6827) has role antibacterial drug (CHEBI:36047)
methicillin (CHEBI:6827) is a penicillin (CHEBI:17334)
methicillin (CHEBI:6827) is a penicillin allergen (CHEBI:88187)
methicillin (CHEBI:6827) is conjugate acid of methicillin(1−) (CHEBI:52064)
Incoming dimethoxyphenylpenicilloyl group (CHEBI:63412) has functional parent methicillin (CHEBI:6827)
methicillin(1−) (CHEBI:52064) is conjugate base of methicillin (CHEBI:6827)
6β-(2,6-dimethoxybenzamido)-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
meticilina ChemIDplus
meticillin ChemIDplus
meticilline ChemIDplus
meticillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6β-(2,6-dimethoxybenzamido)penicillanic acid ChEBI
Manual Xrefs Databases
1744 DrugCentral
DB01603 DrugBank
Meticillin Wikipedia
View more database links
Registry Numbers Types Sources
61-32-5 CAS Registry Number ChemIDplus
966227 Reaxys Registry Number Reaxys
966227 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11969119 PubMed citation Europe PMC
12569987 PubMed citation Europe PMC
24405901 PubMed citation Europe PMC
24433925 PubMed citation Europe PMC
26962156 PubMed citation Europe PMC
Last Modified
12 March 2019