amoxicillin

CHEBI:2676 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:17334 CHEBI:17334
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C16H19N3O5S
Charge	0
Average mass	365.411 Da
Monoisotopic mass	365.10454 Da
Source	ChEBI
InChIKey	LSQZJLSUYDQPKJ-NJBDSQKTSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccc(O)cc1

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

Also called

AMPC (BRAND_NAME)— chebi
Amolin (BRAND_NAME)— chebi
Amopenixin (BRAND_NAME)— chebi
Clamoxyl (BRAND_NAME)— chebi
Moxal (BRAND_NAME)— chebi
amoxicilina (INN)— chebi
amoxicilline (INN)— chebi
amoxicillinum (INN)— chebi
6β-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— chebi
6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid (EXACT_SYNONYM)— chebi
AX (EXACT_SYNONYM)— chebi
Amoxicillin (EXACT_SYNONYM)— chebi
Amoxicillin anhydrous (EXACT_SYNONYM)— chebi
amoxycilin (EXACT_SYNONYM)— chebi
amoxycillin (EXACT_SYNONYM)— chebi
p-hydroxyampicillin (EXACT_SYNONYM)— chebi
α-amino-p-hydroxybenzylpenicillin (EXACT_SYNONYM)— chebi
AMX (EXACT_SYNONYM)— aro
Amoxicilina (EXACT_SYNONYM)— aro
Amoxicilline (EXACT_SYNONYM)— aro
Amoxicillinum (EXACT_SYNONYM)— aro
Amoxycillin (EXACT_SYNONYM)— aro
D-Amoxicillin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000064
cas:26787-78-0
drugbank:DB01060
drugcentral:192
hmdb:HMDB0015193
kegg.compound:C06827
kegg.drug:D07452
lincs.smallmolecule:LSM-5654
patent:DE1942693
patent:GB1241844
patent:GB978178
patent:US3192198
reaxys:4274654
vsdb:1741
wikipedia.en:Amoxicillin
chembl:CHEMBL1082
pubchem.compound:33613

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:0000064`	amoxicillin	`antibioticmech:aro-fbf6a80a9e`	2026-08-30
CHEBI	`CHEBI:2676`	amoxicillin	`antibioticmech:chebi-fa5de6d3c3`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)

Resistance mechanisms

31 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 23

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACI-1	ARO:3004359	not organism-specific	—	ARO:3004359 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
AMZ-1	ARO:3007694	not organism-specific	—	ARO:3007694 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
KBL-1	ARO:3007206	not organism-specific	—	ARO:3007206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
MAB	ARO:3007180	not organism-specific	—	ARO:3007180 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
MUS-1	ARO:3000843	not organism-specific	—	ARO:3000843 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
MUS-2	ARO:3003842	not organism-specific	—	ARO:3003842 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
OXA-1	ARO:3001396	not organism-specific	—	ARO:3001396 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
OXA-2	ARO:3001397	not organism-specific	—	ARO:3001397 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
SED-1	ARO:3003561	not organism-specific	—	ARO:3003561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
SSA	ARO:3007442	not organism-specific	—	ARO:3007442 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
TEM-1	ARO:3000873	not organism-specific	—	ARO:3000873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
TEM-103	ARO:3000966	not organism-specific	—	ARO:3000966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
TEM-30	ARO:3000900	not organism-specific	—	ARO:3000900 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
TUS-1	ARO:3000844	not organism-specific	—	ARO:3000844 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
VMB-1	ARO:3005015	not organism-specific	—	ARO:3005015 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
YRC-1	ARO:3005035	not organism-specific	—	ARO:3005035 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
blaC	ARO:3007182	not organism-specific	—	ARO:3007182 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
blaF	ARO:3003562	not organism-specific	—	ARO:3003562 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 7

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Helicobacter pylori pbp1 mutants conferring resistance to amoxicillin	ARO:3007060	not organism-specific	—	ARO:3007060 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Helicobacter pylori pbp2 mutants conferring resistance to amoxicillin	ARO:3007058	not organism-specific	—	ARO:3007058 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Helicobacter pylori pbp3 conferring resistance to amoxicillin	ARO:3007057	not organism-specific	—	ARO:3007057 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Streptococcus pneumoniae PBP1a conferring resistance to amoxicillin	ARO:3003041	not organism-specific	—	ARO:3003041 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Streptococcus pneumoniae PBP2b conferring resistance to amoxicillin	ARO:3003042	not organism-specific	—	ARO:3003042 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Streptococcus pneumoniae PBP2x conferring resistance to amoxicillin	ARO:3003043	not organism-specific	—	ARO:3003043 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)
Streptococcus pyogenes PBP2x conferring resistance to beta-lactam antibiotics	ARO:3007531	not organism-specific	—	ARO:3007531 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Moraxella catarrhalis M35	ARO:3004124	not organism-specific	—	ARO:3004124 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000064 (amoxicillin); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.