rhizopycnolide A

CHEBI:141316 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A benzochromene that is benzo[c]chromen-6-one which is substituted by hydroxy groups at positions 1, 4 and 7, methoxy groups at positions 3 and 9, a methyl group at position 1, and a 2-carboxy-2-hydroxyethyl group at position 4, and in which the carboxy group has undergone condensation with the 4-hydroxy group to afford the corresponding spirocyclic lactone. It is active against the pathogenic bacteria Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Ralstonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria, with MIC values in the range 25-100 μg/mL. — 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:26878 CHEBI:26878
CHEBI:35681 CHEBI:35681
CHEBI:37581 CHEBI:37581
CHEBI:37948 CHEBI:37948
CHEBI:38920 CHEBI:38920

Chemical structure

Computed structure properties
Molecular formula	C19H20O9
Charge	0
Average mass	392.36 Da
Monoisotopic mass	392.11073 Da
Source	ChEBI
InChIKey	DXDVGVFRBGQXNB-WPZAJUNFSA-N

SMILES

COc1cc(O)c2c(=O)oc3c(c2c1)[C@@](C)(O)C[C@@H](OC)[C@@]31C[C@@H](O)C(=O)O1

InChI

InChI=1S/C19H20O9/c1-18(24)7-12(26-3)19(6-11(21)16(22)28-19)15-14(18)9-4-8(25-2)5-10(20)13(9)17(23)27-15/h4-5,11-12,20-21,24H,6-7H2,1-3H3/t11-,12-,18+,19+/m1/s1

Also called

(1S,3R,4S,4'R)-1,4',7-trihydroxy-3,9-dimethoxy-1-methyl-2,3,3',4'-tetrahydro-1H,5'H,6H-spiro[benzo[c]chromene-4,2'-furan]-5',6-dione (EXACT_SYNONYM)— chebi

Activity roles

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

CHEBI:35718 CHEBI:35718

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:141316`	rhizopycnolide A	`antibioticmech:chebi-da1ec738b6`	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.