pentalenolactone

CHEBI:70816 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A sesquiterpene lactone that is isolated from several Streptomyces species and exhibits antibiotic activity. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:133131 CHEBI:133131
CHEBI:26979 CHEBI:26979
CHEBI:37667 CHEBI:37667
CHEBI:79020 CHEBI:79020

Chemical structure

Computed structure properties
Molecular formula	C15H16O5
Charge	0
Average mass	276.288 Da
Monoisotopic mass	276.09977 Da
Source	ChEBI
InChIKey	NUPNVWUYFVEAIT-UJJBCWTCSA-N

SMILES

[H][C@@]12COC(=O)[C@]3(CO3)[C@@]13C=C(C)[C@@H](C)[C@@]3([H])C=C2C(=O)O

InChI

InChI=1S/C15H16O5/c1-7-4-14-10(8(7)2)3-9(12(16)17)11(14)5-19-13(18)15(14)6-20-15/h3-4,8,10-11H,5-6H2,1-2H3,(H,16,17)/t8-,10-,11+,14-,15-/m1/s1

Also called

(2R,4a'S,7'S,7a'R,9a'R)-6',7'-dimethyl-3'-oxo-1',7',7a',9a'-tetrahydrospiro[oxirane-2,4'-pentaleno[1,6a-c]pyran]-9'-carboxylic acid (EXACT_SYNONYM)— chebi
Arenemycine (EXACT_SYNONYM)— chebi
PA-132 (EXACT_SYNONYM)— chebi
arenaemycin E (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:31501-48-1
metacyc.compound:CPD-13619
reaxys:39567

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
CHEBI	`CHEBI:70816`	pentalenolactone	`antibioticmech:chebi-786a1f574d`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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.