penamecillin

CHEBI:131733 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillanic acid ester that is the acetoxymethyl ester of benzylpenicillin. It is a prodrug for benzylpenicillin. — 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.

penicillanic acid ester CHEBI:51212
Label unavailable CHEBI:72588
penicillin beta-lactam ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C19H22N2O6S
Charge	0
Average mass	406.46 Da
Monoisotopic mass	406.11986 Da
Source	ChEBI
InChIKey	NLOOMWLTUVBWAW-HLLBOEOZSA-N

SMILES

[H][C@]12SC(C)(C)[C@]([H])(C(=O)OCOC(C)=O)N1C(=O)[C@@]2([H])NC(=O)Cc1ccccc1

InChI

InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1

Also called

penamecilina (INN)— chebi
penamecillinum (INN)— chebi
pénamécilline (INN)— chebi
acetoxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (EXACT_SYNONYM)— chebi
Acetoxymethyl benzylpenicillanate (EXACT_SYNONYM)— chebi
Benzylpenicillin acetoxymethyl ester (EXACT_SYNONYM)— chebi

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:3009128`	penamecillin	`antibioticmech:aro-b801a86e62`	2026-08-30
CHEBI	`CHEBI:131733`	penamecillin	`antibioticmech:chebi-00f4b4f521`	2026-08-30

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 2026-09-10 · 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).

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