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> Main
CHEBI:2676 - amoxicillin
Main
ChEBI Ontology
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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
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Wikipedia
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Read full article at Wikipedia
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 (Br
o
nsted 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-[(2
R
)-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
(2
S
,5
R
,6
R
)-
6-
{[(2
R
)-
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
4274654
Beilstein Registry Number
Beilstein
Citations
Types
Sources
10930630
PubMed citation
Europe PMC
11431418
PubMed citation
Europe PMC
11906332
PubMed citation
Europe PMC
12569987
PubMed citation
Europe PMC
12833570
PubMed citation
Europe PMC
12850488
PubMed citation
Europe PMC
16033609
PubMed citation
Europe PMC
2083978
PubMed citation
Europe PMC
24595455
PubMed citation
Europe PMC
24631718
PubMed citation
Europe PMC
24759068
PubMed citation
Europe PMC
25998949
PubMed citation
Europe PMC
27731424
PubMed citation
Europe PMC
28987997
PubMed citation
Europe PMC
29017833
PubMed citation
Europe PMC
Last Modified
14 March 2018