penicillin O

CHEBI:51207 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A penicillin where the side-chain N-acyl group is specified as allylmercaptoacetyl. Antibiotic isolated from Penicillium chrysogenum. — 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:17334 CHEBI:17334

Chemical structure

Computed structure properties
Molecular formula	C13H18N2O4S2
Charge	0
Average mass	330.431 Da
Monoisotopic mass	330.0708 Da
Source	ChEBI
InChIKey	QULKGELYPOJSLP-WCABBAIRSA-N

SMILES

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

InChI

InChI=1S/C13H18N2O4S2/c1-4-5-20-6-7(16)14-8-10(17)15-9(12(18)19)13(2,3)21-11(8)15/h4,8-9,11H,1,5-6H2,2-3H3,(H,14,16)(H,18,19)/t8-,9+,11-/m1/s1

Also called

almecilina (INN)— chebi
almecillin (INN)— chebi
almecilline (INN)— chebi
almecillinum (INN)— chebi
6β-[(prop-2-en-1-ylsulfanyl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(prop-2-en-1-ylsulfanyl)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(allylsulfanyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
allylmercaptomethylpenicillin (EXACT_SYNONYM)— chebi
allylmercaptomethylpenicillinic acid (EXACT_SYNONYM)— chebi
allylthiomethylpenicillin (EXACT_SYNONYM)— chebi
penicillin AT (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:87-09-2
drugcentral:3422
kegg.compound:C17405
patent:US2528175
patent:US2623876
reaxys:44307

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:51207`	penicillin O	`antibioticmech:chebi-2c1345bcb8`	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.