phenoxymethylpenicillin

CHEBI:27446 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin compound having a 6β-(phenoxyacetyl)amino side-chain. — 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.

penicillin CHEBI:17334
penicillin allergen CHEBI:88187
penicillin beta-lactam ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C16H18N2O5S
Charge	0
Average mass	350.396 Da
Monoisotopic mass	350.09364 Da
Source	ChEBI
InChIKey	BPLBGHOLXOTWMN-MBNYWOFBSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)COc1ccccc1

InChI

InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

Also called

Fenospen (BRAND_NAME)— chebi
V-Cillin (BRAND_NAME)— chebi
fenoximetilpenicilina (INN)— chebi
phenoxymethylpenicillinum (INN)— chebi
phénoxyméthylpénicilline (INN)— chebi
2,2-dimethyl-6β-[(phenoxyacetyl)amino]penam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
3,3-dimethyl-6β-[(phenoxyacetyl)amino]penam-2α-carboxylic acid (PIN) (EXACT_SYNONYM)— chebi
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1- AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID (EXACT_SYNONYM)— chebi
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
6-phenoxyacetamidopenicillanic acid (EXACT_SYNONYM)— chebi
Oracillin (EXACT_SYNONYM)— chebi
PV (EXACT_SYNONYM)— chebi
Penicillin V (EXACT_SYNONYM)— chebi
penicillin phenoxymethyl (EXACT_SYNONYM)— chebi
phenoxomethylpenicillin (EXACT_SYNONYM)— chebi
phenoxymethylenepenicillinic acid (EXACT_SYNONYM)— chebi
penicillin V (EXACT_SYNONYM)— aro
phenomycilline (EXACT_SYNONYM)— aro
phenopenicillin (EXACT_SYNONYM)— aro

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.

wikipedia.en:Phenoxymethylpenicillin

Activity roles

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

antimicrobial agent 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:3000633`	phenoxymethylpenicillin	`antibioticmech:aro-5455d345e8`	2026-08-30
CHEBI	`CHEBI:27446`	phenoxymethylpenicillin	`antibioticmech:chebi-bba43ddac4`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:3000633 (phenoxymethylpenicillin); database assertion, not a primary citation.)

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 2026-08-31 · 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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