deguelin

CHEBI:4357 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. — 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:35618 CHEBI:35618
CHEBI:38164 CHEBI:38164
CHEBI:46786 CHEBI:46786
CHEBI:72581 CHEBI:72581

Chemical structure

Computed structure properties
Molecular formula	C23H22O6
Charge	0
Average mass	394.423 Da
Monoisotopic mass	394.14164 Da
Source	ChEBI
InChIKey	ORDAZKGHSNRHTD-UXHICEINSA-N

SMILES

[H][C@@]12COc3cc(OC)c(OC)cc3[C@]1([H])C(=O)c1ccc3c(c1O2)C=CC(C)(C)O3

InChI

InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

Also called

(7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one (EXACT_SYNONYM)— chebi
(7aS,13aS)-13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one (EXACT_SYNONYM)— chebi
(7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-7(7aH)-one (EXACT_SYNONYM)— chebi
(−)-cis-deguelin (EXACT_SYNONYM)— chebi
(−)-deguelin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:522-17-8
chemspider:97058
hmdb:HMDB0250941
kegg.compound:C10417
knapsack:C00002522
lincs.smallmolecule:LSM-3368
lipidmaps:LMPK12060019
metacyc.compound:CPD-12163
wikipedia.en:Deguelin

Activity roles

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

CHEBI:22587 CHEBI:22587

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:4357`	deguelin	`antibioticmech:chebi-e3d069886f`	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.