benzylpenicillin

CHEBI:18208 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido 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	C16H18N2O4S
Charge	0
Average mass	334.397 Da
Monoisotopic mass	334.09873 Da
Source	ChEBI
InChIKey	JGSARLDLIJGVTE-MBNYWOFBSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)Cc1ccccc1

InChI

InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

Also called

bencilpenicilina (INN)— chebi
benzylpenicillinum (INN)— chebi
benzylpénicilline (INN)— chebi
2,2-dimethyl-6β-(phenylacetamido)penam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
6-(2-phenylacetamido)penicillanic acid (EXACT_SYNONYM)— chebi
Benzylpenicillin (EXACT_SYNONYM)— chebi
PCG (EXACT_SYNONYM)— chebi
PENICILLIN G (EXACT_SYNONYM)— chebi
PG (EXACT_SYNONYM)— chebi
Penicillin G (EXACT_SYNONYM)— chebi
bensylpenicillin (EXACT_SYNONYM)— chebi
benzyl benicillin (EXACT_SYNONYM)— chebi
benzylpenicillinic acid (EXACT_SYNONYM)— chebi
free penicillin II (EXACT_SYNONYM)— chebi
benzopenicillin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000632
cas:61-33-6
drugbank:DB01053
drugcentral:2082
gmelin:781913
hmdb:HMDB0015186
kegg.compound:C05551
kegg.drug:D02336
lincs.smallmolecule:LSM-3229
patent:US3024169
pdb-ccd:PNN
reaxys:44740
wikipedia.en:Benzylpenicillin
chembl:CHEMBL29
pubchem.compound:5904

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:3000632`	benzylpenicillin	`antibioticmech:aro-558ace57e8`	2026-08-30
CHEBI	`CHEBI:18208`	benzylpenicillin	`antibioticmech:chebi-ac69226a2d`	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:3000632 (benzylpenicillin); database assertion, not a primary citation.)

Resistance mechanisms

10 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 8

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
AMZ-1	ARO:3007694	not organism-specific	—	ARO:3007694 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
KBL-1	ARO:3007206	not organism-specific	—	ARO:3007206 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
LAQ-1	ARO:3007438	not organism-specific	—	ARO:3007438 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
Rhodobacter sphaeroides ampC beta-lactamase	ARO:3004291	not organism-specific	—	ARO:3004291 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 2

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Burkholderia pseudomallei Omp38	ARO:3004123	not organism-specific	—	ARO:3004123 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000632 (benzylpenicillin); 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

Provenance

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