3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose

CHEBI:65753 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An ent-kaurane diterpenoid that is ent-kaur-16-en-18-oic acid substituted by a β-L-3',5'-diacetoxy-arabinofuranosyl moiety at position 18 via a glycosidic linkage. It is isolated from the whole herb of Sagittaria pygmaea and exhibits antibacterial activity against the oral pathogens. — 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:36760 CHEBI:36760
CHEBI:47622 CHEBI:47622

Chemical structure

Computed structure properties
Molecular formula	C29H42O8
Charge	0
Average mass	518.647 Da
Monoisotopic mass	518.28797 Da
Source	ChEBI
InChIKey	NDNXVUYCJZMRRS-ABRNDMKOSA-N

SMILES

[H][C@]12CC[C@]34CC(=C)[C@H](CC[C@@]3([H])[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]1O[C@@H](COC(C)=O)[C@H](OC(C)=O)[C@H]1O)C4

InChI

InChI=1S/C29H42O8/c1-16-13-29-12-9-21-27(4,22(29)8-7-19(16)14-29)10-6-11-28(21,5)26(33)37-25-23(32)24(35-18(3)31)20(36-25)15-34-17(2)30/h19-25,32H,1,6-15H2,2-5H3/t19?,20-,21-,22-,23+,24-,25+,27+,28+,29+/m0/s1

Also called

18-β-L-3',5'-diacetoxy-arabinofuranosyl-ent-kaur-16-ene (EXACT_SYNONYM)— chebi

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:65753`	3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose	`antibioticmech:chebi-19e345b19d`	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.