lenampicillin

CHEBI:135748 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A penicillanic acid ester that is the (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of ampicillin. It is a prodrug of ampicillin. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:145408 CHEBI:145408
CHEBI:51212 CHEBI:51212

Chemical structure

Computed structure properties
Molecular formula	C21H23N3O7S
Charge	0
Average mass	461.496 Da
Monoisotopic mass	461.12567 Da
Source	ChEBI
InChIKey	ZKUKMWMSYCIYRD-ZXFNITATSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)OCc3oc(=O)oc3C)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1

InChI

InChI=1S/C21H23N3O7S/c1-10-12(31-20(28)30-10)9-29-19(27)15-21(2,3)32-18-14(17(26)24(15)18)23-16(25)13(22)11-7-5-4-6-8-11/h4-8,13-15,18H,9,22H2,1-3H3,(H,23,25)/t13-,14-,15+,18-/m1/s1

Also called

lenampicilina (INN)— chebi
lenampicillinum (INN)— chebi
lénampicilline (INN)— chebi
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (EXACT_SYNONYM)— chebi
KBT 1585 (EXACT_SYNONYM)— chebi
KBT-1585 (EXACT_SYNONYM)— chebi
ampicillin 5-methyl-2-oxo-1,3-dioxol-4-yl methyl ester (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:86273-18-9
drugcentral:1553
kegg.drug:D08110

Activity roles

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

CHEBI:33281 CHEBI:33281

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
CHEBI	`CHEBI:135748`	lenampicillin	`antibioticmech:chebi-93a20a1ef6`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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

Provenance

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