CHEBI:2676 - amoxicillin

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ChEBI Name amoxicillin
ChEBI ID CHEBI:2676
Definition A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:133770
Supplier Information eMolecules:2724871, eMolecules:29780576, Selleckchem:amoxicillin-amoxycillin, ZINC000003830215
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Formula C16H19N3O5S
Net Charge 0
Average Mass 365.40400
Monoisotopic Mass 365.10454
InChI InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
InChIKey LSQZJLSUYDQPKJ-NJBDSQKTSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccc(O)cc1)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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amoxicillin (CHEBI:2676) has role antibacterial drug (CHEBI:36047)
amoxicillin (CHEBI:2676) is a penicillin (CHEBI:17334)
amoxicillin (CHEBI:2676) is a penicillin allergen (CHEBI:88187)
amoxicillin (CHEBI:2676) is conjugate acid of amoxicillin(1−) (CHEBI:51256)
Incoming amoxicillin diketopiperazine (CHEBI:60639) has functional parent amoxicillin (CHEBI:2676)
amoxicilloyl polylysine (CHEBI:133951) has functional parent amoxicillin (CHEBI:2676)
amoxicilloyl-L-lysine (CHEBI:139366) has functional parent amoxicillin (CHEBI:2676)
amoxicilloyl-butylamine (CHEBI:55470) has functional parent amoxicillin (CHEBI:2676)
amoxicillin trihydrate (CHEBI:51254) has part amoxicillin (CHEBI:2676)
amoxicillin(1−) (CHEBI:51256) is conjugate base of amoxicillin (CHEBI:2676)
amoxicillanyl group (CHEBI:53712) is substituent group from amoxicillin (CHEBI:2676)
amoxicilloyl group (CHEBI:53705) is substituent group from amoxicillin (CHEBI:2676)
ampicillanyl group (CHEBI:53713) is substituent group from amoxicillin (CHEBI:2676)
IUPAC Name
6β-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
amoxicilina ChemIDplus
amoxicillin KEGG DRUG
amoxicilline ChemIDplus
amoxicillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid ChemIDplus
α-amino-p-hydroxybenzylpenicillin ChemIDplus
Amoxicillin KEGG COMPOUND
Amoxicillin anhydrous KEGG COMPOUND
amoxycilin ChEBI
amoxycillin ChemIDplus
AX ChEBI
p-hydroxyampicillin ChemIDplus
Brand Names Sources
Amolin DrugBank
Amopenixin DrugBank
AMPC DrugBank
Clamoxyl ChemIDplus
Moxal DrugBank
Manual Xrefs Databases
1741 VSDB
192 DrugCentral
Amoxicillin Wikipedia
C06827 KEGG COMPOUND
D07452 KEGG DRUG
DB01060 DrugBank
DE1942693 Patent
GB1241844 Patent
GB978178 Patent
HMDB0015193 HMDB
LSM-5654 LINCS
US3192198 Patent
View more database links
Registry Numbers Types Sources
26787-78-0 CAS Registry Number KEGG COMPOUND
26787-78-0 CAS Registry Number ChemIDplus
4274654 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10930630 PubMed citation Europe PMC
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Last Modified
14 March 2018