castanospermine

CHEBI:27860 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer). — 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:38511 CHEBI:38511

Chemical structure

Computed structure properties
Molecular formula	C8H15NO4
Charge	0
Average mass	189.211 Da
Monoisotopic mass	189.10011 Da
Source	ChEBI
InChIKey	JDVVGAQPNNXQDW-TVNFTVLESA-N

SMILES

[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O

InChI

InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

Also called

(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol (EXACT_SYNONYM)— chebi
(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine (EXACT_SYNONYM)— chebi
(1S-(1α,6β,7α,8β,8αβ))-octahydro-1,6,7,8-indolizinetetrol (EXACT_SYNONYM)— chebi
1,6,7,8-tetrahydroxyoctahydroindolizine (EXACT_SYNONYM)— chebi
CASTANOSPERMINE (EXACT_SYNONYM)— chebi
Castanospermine (EXACT_SYNONYM)— chebi
castinospermine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:79831-76-8
kegg.compound:C02256
knapsack:C00002028
patent:KR20070061879
patent:MX2009004170
patent:US5837709
pdb-ccd:CTS
reaxys:3588654
wikipedia.en:Castanospermine

Activity roles

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

CHEBI:64947 CHEBI:64947

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:27860`	castanospermine	`antibioticmech:chebi-933d86bc22`	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.