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.

CHEBI:51212 CHEBI:51212
CHEBI:72588 CHEBI:72588
ARO:3000008 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

Equivalent identifiers for this same structure in other resources.

ARO:3009128
cas:983-85-7
drugcentral:2077
kegg.drug:D05406
patent:GB1003479
patent:US3250679
reaxys:5164412
wikipedia.en:Penamecillin
chembl:CHEMBL2106988
pubchem.compound:10250769

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: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

Provenance

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