piericidin A

CHEBI:138511 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A member of the class of monohydroxypyridines that acts as an irreversible mitochondrial Complex I inhibitor that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of NADH:ubiquinone oxidoreductase — 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:134396 CHEBI:134396
CHEBI:25340 CHEBI:25340
CHEBI:35618 CHEBI:35618
CHEBI:38182 CHEBI:38182

Chemical structure

Computed structure properties
Molecular formula	C25H37NO4
Charge	0
Average mass	415.574 Da
Monoisotopic mass	415.27226 Da
Source	ChEBI
InChIKey	BBLGCDSLCDDALX-LKGBESRRSA-N

SMILES

C/C=C(\C)[C@H](O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1nc(OC)c(OC)c(O)c1C

InChI

InChI=1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1

Also called

2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol (EXACT_SYNONYM)— chebi
(+)-piericidin A1 (EXACT_SYNONYM)— chebi
2-[(2E,5E,7E,11E)-10R-hydroxy-3,7,9R,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4-pyridinol (EXACT_SYNONYM)— chebi
2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one (EXACT_SYNONYM)— chebi
AR 054 (EXACT_SYNONYM)— chebi
Piericidin A1 (EXACT_SYNONYM)— chebi
SN 198E (EXACT_SYNONYM)— chebi
Shaoguanmycin B (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:2738-64-9
metacyc.compound:CPD0-1233
reaxys:4720916

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:138511`	piericidin A	`antibioticmech:chebi-e110475a2b`	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.