AntibioticMech

phenoxymethylpenicillin

CHEBI:27446 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

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	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

Equivalent identifiers for this same structure in other resources.

• ARO:3000633
• cas:87-08-1
• drugbank:DB00417
• drugcentral:2083
• kegg.compound:C08126
• kegg.drug:D05411
• pdb-ccd:PNV
• reaxys:96259
• wikipedia.en:Phenoxymethylpenicillin
• chembl:CHEMBL615
• pubchem.compound:6869

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: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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · 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.