Compound: castanospermine
SMILES: O[C@H]1[C@H](O)[C@@H]2N(CC[C@@H]2O)C[C@@H]1O
InChIKey: JDVVGAQPNNXQDW-TVNFTVLESA-N
Synonyms: castanospermine, 79831-76-8, Castinospermine, 1,6,7,8-Tetrahydroxyoctahydroindolizine, (+)-Castanospermine, (1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol, (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol, Q0I3184XM7, NSC-625381, CHEBI:27860, DTXSID601026043, (1S-(1alpha,6beta,7alpha,8beta,8alphabeta))-octahydro-1,6,7,8-indolizinetetrol, RefChem:574815, DTXCID101510299, (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 6,7-Diepicastanospermine, MFCD00017555, (1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetraol, CTS, SR-01000597675, NSC 625381, UNII-Q0I3184XM7, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol, Indolizine der., NSC625381, 2cbu, Octahydro-indolizine-1,6,7,8-tetraol, 79831-76-8 (free base), CID54445, CAST, MolMap_000013, UPCMLD-DP122, CASTANOSPERMINE [MI], SCHEMBL61040, BSPBio_001552, KBioGR_000272, KBioSS_000272, MLS000028641, CHEMBL311226, UPCMLD-DP122:001, UPCMLD-DP122:002, UPCMLD-DP122:003, BCBcMAP01_000133, BDBM36388, KBio2_000272, KBio2_002840, KBio2_005408, KBio3_000543, KBio3_000544, Bio1_000396, Bio1_000885, Bio1_001374, Bio2_000272, Bio2_000752, GLXC-03822, HMS1361N14, HMS1791N14, HMS1989N14, HMS2232G11, HMS3266B08, HMS3402N14, HMS3414H05, HMS3678H05, HY-N2022, EBC-75135, AKOS024458634, CCG-208170, CS-5633, DB01816, MC08277, IDI1_034022, SMP1_000059, NCGC00024773-02, NCGC00024773-04, SMR000059227, NS00069171, Octahydro-indolizine-1,6,7,8-tetraol, 13, C02256, EN300-7407999, Q753104, SR-01000597675-1, SR-01000597675-4, BRD-K20897876-001-10-0, CASTANOSPERMINE FROM CASTANOSPERMUM AUSTRALE SEEDS, 81041B9A-D148-44DC-A86D-C78D6ABF9633, (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%, 1,6,7,8-Indolizinetetrol, octahydro-,?(1S,6S,7R,8R,8aR)-, Castanospermine, >=94% (GC), BioUltra, from Castanospermum australe seeds, 1,6,7,8-Indolizinetetrol, octahydro-, (1S-(1alpha,6beta,7alpha,8beta,8abeta))-
Theoretical properties:
molecular_formula: C8H15NO4
molecular_weight: 189.21 g/mol
exact_mass: 189.10010796 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 0
heavy_atom_count: 13
topological_polar_surface_area: 84.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Castanospermine is 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). It has a role as a metabolite, an EC 3.2.1.* (glycosidase) inhibitor, an anti-HIV-1 agent and an anti-inflammatory agent.
chebi: A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1<i>S</i>,6<i>S</i>,7<i>R</i>,8<i>R</i>,8a<i>R</i>-diastereomer).
chembl: CASTANOSPERMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: 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.
The castanospermine derivative celgosivir is an antiviral drug candidate that as of 2009 was in development for possible use in treating hepatitis C virus (HCV) infection.