Castanospermine

Castanospermine

Names
IUPAC name (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
Identifiers
CAS Number	79831-76-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27860 N
ChemSpider	49177 N
ECHA InfoCard	100.127.469
PubChem CID	54445
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 N Key: JDVVGAQPNNXQDW-TVNFTVLESA-N N InChI=1/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 Key: JDVVGAQPNNXQDW-TVNFTVLEBE
SMILES O[C@H]1CCN2[C@H]1[C@@H](O)[C@H](O)[C@@H](O)C2
Properties
Chemical formula	C8H15NO4
Molar mass	189.209 g/mol
Appearance	White to off-white solid
Melting point	212 to 215 °C (414 to 419 °F; 485 to 488 K)
Solubility in water	Soluble
Hazards
R-phrases (outdated)	R20/21/22
S-phrases (outdated)	S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe. It is a potent inhibitor of some glucosidase enzymes and has antiviral activity in vitro and in mouse models.

Castanospermine was a lead to celgosivir.