piperacillin

CHEBI:8232 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-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.

penicillin CHEBI:17334
penicillin allergen CHEBI:88187
penicillin beta-lactam ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C23H27N5O7S
Charge	0
Average mass	517.564 Da
Monoisotopic mass	517.16312 Da
Source	ChEBI
InChIKey	IVBHGBMCVLDMKU-GXNBUGAJSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)c1ccccc1

InChI

InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1

Also called

6β-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
Piperacillin (EXACT_SYNONYM)— chebi
Piperacillin anhydrous (EXACT_SYNONYM)— chebi
Piperacillin sodium (EXACT_SYNONYM)— aro
Pipercillin (EXACT_SYNONYM)— aro
Pipracil (EXACT_SYNONYM)— aro
Pipril (EXACT_SYNONYM)— aro

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial drug 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:0000078`	piperacillin	`antibioticmech:aro-923e37e9cc`	2026-08-30
CHEBI	`CHEBI:8232`	piperacillin	`antibioticmech:chebi-166ba03674`	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:0000078 (piperacillin); database assertion, not a primary citation.)

Resistance mechanisms

16 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_INACTIVATION 15

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACC-1	ARO:3001815	not organism-specific	—	ARO:3001815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
Acinetobacter baumannii ampC beta-lactamase	ARO:3003796	not organism-specific	—	ARO:3003796 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
EBR-5	ARO:3007437	not organism-specific	—	ARO:3007437 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
KBL-1	ARO:3007206	not organism-specific	—	ARO:3007206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
MUS-1	ARO:3000843	not organism-specific	—	ARO:3000843 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
MUS-2	ARO:3003842	not organism-specific	—	ARO:3003842 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
OXA-1	ARO:3001396	not organism-specific	—	ARO:3001396 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
SED-1	ARO:3003561	not organism-specific	—	ARO:3003561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
TUS-1	ARO:3000844	not organism-specific	—	ARO:3000844 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
VIM-92	ARO:3009643	not organism-specific	—	ARO:3009643 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae KpnGH-TolC	ARO:3004598	not organism-specific	—	ARO:3004598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000078 (piperacillin); 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 2026-09-10 · 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 (YAML).

Explore across X-Mech: MediaIngredientMech (piperacillin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech