lupulin A

CHEBI:66597 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A diterpenoid isolated from Ajuga lupulina and has been shown to exhibit anti-inflammatory and antibacterial activities. — 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:23849 CHEBI:23849
CHEBI:32955 CHEBI:32955
CHEBI:47622 CHEBI:47622
CHEBI:47790 CHEBI:47790

Chemical structure

Computed structure properties
Molecular formula	C30H46O11
Charge	0
Average mass	582.687 Da
Monoisotopic mass	582.30401 Da
Source	ChEBI
InChIKey	UEZOFWAZJUOMCN-HKDNVZQMSA-N

SMILES

[H][C@]12C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]3(CO3)[C@]1(COC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@]2(C)[C@]1([H])CC2C[C@H](OC)OC2O1

InChI

InChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15?,16-,19?,20-,21-,22+,23+,24-,25+,27?,28+,29+,30-/m1/s1

Also called

(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5-[(2S,5R)-5-methoxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8528547

Activity roles

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

CHEBI:33282 CHEBI:33282

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:66597`	lupulin A	`antibioticmech:chebi-5b33033102`	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.