Compound: swainsonine
SMILES: O[C@H]1[C@H]2N(CCC1)C[C@H]([C@H]2O)O
InChIKey: FXUAIOOAOAVCGD-WCTZXXKLSA-N
Synonyms: swainsonine, Tridolgosir, 72741-87-8, DTXSID5046356, RSY4RK37KQ, (1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol, (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol, 1,2,8-Indolizinetriol, octahydro-, (1S-(1alpha,2alpha,8beta,8abeta))-, CHEBI:9367, DTXCID3026356, tridolgosirum, RefChem:890073, (-)-Swainsonine, Tridolgosir [INN], Swainsonine (Synthetic), MFCD00017554, (1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol, 1S-8AB-OCTAHYDRO-INDOLIZIDINE-1A,2A,8B-TRIOL, CHEMBL371197, NCGC00163481-02, SWA, UNII-RSY4RK37KQ, Swainosine, Locoweed deriv., NSC614553, 1hww, Octahydro-1,2,8-indolizinetriol hydrochloride, A1IGC, GlyTouCan:G66979UZ, CBiol_001919, BSPBio_001148, KBioGR_000488, KBioSS_000488, TRIDOLGOSIR [WHO-DD], orb419474, CHEMBL63139, SCHEMBL765848, (-)-(1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine Hydrochloride, KBio2_000488, KBio2_003056, KBio2_005624, KBio3_000895, KBio3_000896, Bio1_000205, Bio1_000694, Bio1_001183, Bio2_000414, Bio2_000894, GLXC-22773, HMS1362J09, HMS1792J09, HMS1990J09, HMS3403J09, Octahydro-indolizine-1,2,8-triol, G66979UZ, HY-N6722, Tox21_112058, BDBM50016706, BDBM50168995, (1S,2R,8aR)-Octahydroindolizinetriol, AKOS016344385, CCG-208274, DB02034, MS10129, NSC-614553, IDI1_002169, SMP1_000286, NCGC00163481-03, NCGC00163481-04, AC-34386, CAS-72741-87-8, CS-0015643, NS00037401, (1S, 2R, 8R, 8AR)-1,2,8-Indolizidinetriol, Q415324, SR-05000002325, SR-05000002325-2, (1S,2R,8R,8aR)-Octahydro-indolizine-1,2,8-triol, 1,8-Indolizinetriol, octahydro-, (1S,2R,8R,8aR)-, BRD-K15170068-001-03-2, 1,2,8-Indolizinetriol, octahydro-, (1S,2R,8R,8aR)-, CFCE4066-9132-492F-B4E1-B50B974FE148, (1S,2R,8R,8?R)-1,2,3,5,6,7,8,8?-Octahydroindolizine-1,2,8-triol, 1,2,8-INDOLIZINETRIOL, OCTAHYDRO-, (1S-(1.ALPHA.,2.ALPHA.,8.BETA.,8A.BETA.))-, 1,8-Indolizinetriol, octahydro-,[1S-(1.alpha.,2.alpha., 8.beta.,8a.beta.)]-
Theoretical properties:
molecular_formula: C8H15NO3
molecular_weight: 173.21 g/mol
exact_mass: 173.10519334 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 12
topological_polar_surface_area: 63.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 143-144 °C
Descriptions:
pubchem: Swainsonine is an indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8. It has a role as an antineoplastic agent, an immunological adjuvant, an EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor and a plant metabolite.
chebi: An indolizidine alkaloid isolated from the plant <em>Swainsona canescens</em> with three hydroxy substituents at positions 1, 2 and 8.
chembl: TRIDOLGOSIR is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Swainsonine is an indolizidine alkaloid.  It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug. As a toxin in locoweed (likely its primary toxin) it also is a significant cause of economic losses in livestock industries, particularly in North America. It was first isolated from Swainsona canescens.