SWA

1S-8AB-OCTAHYDRO-INDOLIZIDINE-1A,2A,8B-TRIOL

Created:	2001-01-15
Last modified:	2020-06-05

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5 entries where SWA is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	27
Chiral Atom Count	4
Bond Count	28
Aromatic Bond Count	0

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Chemical Component Summary
Name	1S-8AB-OCTAHYDRO-INDOLIZIDINE-1A,2A,8B-TRIOL
Synonyms	SWAINSONINE
Systematic Name (OpenEye OEToolkits)	(1S,2R,4R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
Formula	C₈ H₁₅ N O₃
Molecular Weight	173.21
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	OC1CCCN2C1C(O)C(O)C2
SMILES	CACTVS	3.341	O[CH]1CCCN2C[CH](O)[CH](O)[CH]12
SMILES	OpenEye OEToolkits	1.5.0	C1CC(C2C(C(CN2C1)O)O)O
Canonical SMILES	CACTVS	3.341	O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)[C@@H]12
Canonical SMILES	OpenEye OEToolkits	1.5.0	C1C[C@H]([C@@H]2[C@@H]([C@@H](C[N@]2C1)O)O)O
InChI	InChI	1.03	InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
InChIKey	InChI	1.03	FXUAIOOAOAVCGD-WCTZXXKLSA-N

Drug Info: DrugBank

DrugBank ID	DB02034
Name	Tridolgosir
Groups	experimental
Description	An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.
Synonyms	Swainosine Tridolgosir hydrochloride Tridolgosir (1S,2R,8R,8AR)-octahydro-1,2,8-indolizinetriol
CAS number	72741-87-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Alpha-mannosidase 2	MKLSRQFTVFGSAIFCVVIFSLYLMLDRGHLDYPRNPRREGSFPQGQLSM...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682