epicillin

CHEBI:58974 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido 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.

CHEBI:17334 CHEBI:17334
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C16H21N3O4S
Charge	0
Average mass	351.428 Da
Monoisotopic mass	351.12528 Da
Source	ChEBI
InChIKey	RPBAFSBGYDKNRG-NJBDSQKTSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1

InChI

InChI=1S/C16H21N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-4,7,9-11,14H,5-6,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

Also called

epicilina (INN)— chebi
epicilline (INN)— chebi
epicillinum (INN)— chebi
6β-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
Dexacillin (EXACT_SYNONYM)— chebi
Dihydroampicillin (EXACT_SYNONYM)— chebi
dexacillin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009131
cas:26774-90-3
drugcentral:1025
patent:DE2161659
reaxys:1091831
wikipedia.en:Epicillin
chembl:CHEMBL2104266
pubchem.compound:71392

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
ARO	`ARO:3009131`	epicillin	`antibioticmech:aro-0f226030c6`	2026-08-30
CHEBI	`CHEBI:58974`	epicillin	`antibioticmech:chebi-173aad2657`	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.