temocillin

CHEBI:51817 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin compound having a 6α-methoxy and 6β-[2-carboxy(thiophen-3-yl)acetamido side-groups. — 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
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C16H18N2O7S2
Charge	0
Average mass	414.461 Da
Monoisotopic mass	414.05554 Da
Source	ChEBI
InChIKey	BVCKFLJARNKCSS-DWPRYXJFSA-N

SMILES

[H]C(C(=O)O)(C(=O)N[C@]1(OC)C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@@]21[H])c1ccsc1

InChI

InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1

Also called

temocillina (INN)— chebi
temocilline (INN)— chebi
temocillinum (INN)— chebi
6β-[carboxy(thiophen-3-yl)acetamido]-6-methoxy-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6S)-6-[2-carboxy(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6S)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6S)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
N-((2S,5R,6S)-2-carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-3-thiophenemalonamic acid (EXACT_SYNONYM)— chebi
BRL 17421 (EXACT_SYNONYM)— aro
Temocilline (EXACT_SYNONYM)— aro
Temocillinum (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3003831
cas:66148-78-5
drugcentral:2587
kegg.drug:D06064
patent:DE2600866
reaxys:1094670
chembl:CHEMBL1276310
pubchem.compound:171758

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:3003831`	temocillin	`antibioticmech:aro-c18540f369`	2026-08-30
CHEBI	`CHEBI:51817`	temocillin	`antibioticmech:chebi-fa51383c48`	2026-08-30

Resistance mechanisms

2 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 2

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
OXA-48	ARO:3001782	not organism-specific	—	ARO:3001782 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003831 (temocillin); database assertion, not a primary citation.)
blaC	ARO:3007182	not organism-specific	—	ARO:3007182 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003831 (temocillin); 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

Provenance

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