ampicillin

CHEBI:28971 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido 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:27933 CHEBI:27933
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C16H19N3O4S
Charge	0
Average mass	349.412 Da
Monoisotopic mass	349.10963 Da
Source	ChEBI
InChIKey	AVKUERGKIZMTKX-NJBDSQKTSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1

InChI

InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

Also called

ampicilina (INN)— chebi
ampicilline (INN)— chebi
ampicillinum (INN)— chebi
6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
6-(D-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
ABPC (EXACT_SYNONYM)— chebi
AMP (EXACT_SYNONYM)— chebi
AP (EXACT_SYNONYM)— chebi
Ampicillin (EXACT_SYNONYM)— chebi
Anhydrous ampicillin (EXACT_SYNONYM)— chebi
D-(−)-6-(α-aminophenylacetamido)penicillanic acid (EXACT_SYNONYM)— chebi
D-(−)-ampicillin (EXACT_SYNONYM)— chebi
aminobenzylpenicillin (EXACT_SYNONYM)— chebi
ampicillin acid (EXACT_SYNONYM)— chebi
ampicillin anhydrous (EXACT_SYNONYM)— chebi
Principen (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000637
cas:69-53-4
drugbank:DB00415
drugcentral:198
hmdb:HMDB0014559
kegg.compound:C06574
kegg.drug:D00204
lincs.smallmolecule:LSM-5761
patent:GB902703
patent:US2985648
patent:US3157640
pdb-ccd:AIC
pdb-ccd:PN1
reaxys:4300240
vsdb:1849
wikipedia.en:Ampicillin
chembl:CHEMBL174
pubchem.compound:6249

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:3000637`	ampicillin	`antibioticmech:aro-60a0e570fd`	2026-08-30
CHEBI	`CHEBI:28971`	ampicillin	`antibioticmech:chebi-ae6873a4e5`	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:3000637 (ampicillin); database assertion, not a primary citation.)

Resistance mechanisms

37 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 31

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
AMZ-1	ARO:3007694	not organism-specific	—	ARO:3007694 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
CTX-M-15	ARO:3001878	not organism-specific	—	ARO:3001878 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
CTX-M-27	ARO:3001889	not organism-specific	—	ARO:3001889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
EBR-5	ARO:3007437	not organism-specific	—	ARO:3007437 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
KBL-1	ARO:3007206	not organism-specific	—	ARO:3007206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
LAQ-1	ARO:3007438	not organism-specific	—	ARO:3007438 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
NmcA	ARO:3003589	not organism-specific	—	ARO:3003589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
OXA-1	ARO:3001396	not organism-specific	—	ARO:3001396 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
OXA-2	ARO:3001397	not organism-specific	—	ARO:3001397 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
OXA-50	ARO:3001796	not organism-specific	—	ARO:3001796 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
PJM-1	ARO:3007374	not organism-specific	—	ARO:3007374 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
SHV-1	ARO:3001059	not organism-specific	—	ARO:3001059 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
SSA	ARO:3007442	not organism-specific	—	ARO:3007442 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
TEM beta-lactamase	ARO:3000014	not organism-specific	—	ARO:3000014 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
TEM-1	ARO:3000873	not organism-specific	—	ARO:3000873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
TEM-103	ARO:3000966	not organism-specific	—	ARO:3000966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
TEM-30	ARO:3000900	not organism-specific	—	ARO:3000900 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
VAM-1	ARO:3007062	not organism-specific	—	ARO:3007062 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
VHH-1	ARO:3007003	not organism-specific	—	ARO:3007003 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
VHW-1	ARO:3007004	not organism-specific	—	ARO:3007004 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
VIM-63	ARO:3005511	not organism-specific	—	ARO:3005511 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
VMB-1	ARO:3005015	not organism-specific	—	ARO:3005015 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
WUS-1	ARO:3007435	not organism-specific	—	ARO:3007435 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 3

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AcrAB-TolC	ARO:3000384	not organism-specific	—	ARO:3000384 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
MexAB-OprM	ARO:3000386	not organism-specific	—	ARO:3000386 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)
mdeA	ARO:3007011	not organism-specific	—	ARO:3007011 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Haemophilus influenzae PBP3 conferring resistance to beta-lactam antibiotics	ARO:3004446	not organism-specific	—	ARO:3004446 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); 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:3000637 (ampicillin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000637 (ampicillin); 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
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.