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Identification
NameSwainsonine
Accession NumberDB02034  (EXPT02983)
TypeSmall Molecule
GroupsExperimental
Description

An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity. [PubChem]

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number72741-87-8
WeightAverage: 173.2096
Monoisotopic: 173.105193351
Chemical FormulaC8H15NO3
InChI KeyFXUAIOOAOAVCGD-FKSUSPILSA-N
InChI
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+/m0/s1
IUPAC Name
(1S,2R,8S,8aS)-octahydroindolizine-1,2,8-triol
SMILES
O[C@@H]1CN2CCC[C@H](O)[C@H]2[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndolizidines
Sub ClassNot Available
Direct ParentIndolizidines
Alternative Parents
Substituents
  • Indolizidine
  • N-alkylpyrrolidine
  • Piperidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9652
Blood Brain Barrier+0.5273
Caco-2 permeable-0.5141
P-glycoprotein substrateSubstrate0.6622
P-glycoprotein inhibitor INon-inhibitor0.8542
P-glycoprotein inhibitor IINon-inhibitor0.9732
Renal organic cation transporterNon-inhibitor0.6424
CYP450 2C9 substrateNon-substrate0.8769
CYP450 2D6 substrateNon-substrate0.6593
CYP450 3A4 substrateNon-substrate0.5136
CYP450 1A2 substrateNon-inhibitor0.7861
CYP450 2C9 substrateNon-inhibitor0.9292
CYP450 2D6 substrateNon-inhibitor0.9075
CYP450 2C19 substrateNon-inhibitor0.9214
CYP450 3A4 substrateNon-inhibitor0.9972
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9921
Ames testNon AMES toxic0.7576
CarcinogenicityNon-carcinogens0.9722
BiodegradationNot ready biodegradable0.9773
Rat acute toxicity2.3774 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6501
hERG inhibition (predictor II)Non-inhibitor0.8976
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point143-144 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility1320.0 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.4ChemAxon
logS0.88ALOGPS
pKa (Strongest Acidic)13.28ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.93 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.12 m3·mol-1ChemAxon
Polarizability18.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

William H. Pearson, Erik J. Hembre, “Method for preparing swainsonine.” U.S. Patent US5919952, issued December, 1986.

US5919952
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Alpha-mannosidase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-mannosidase 2 Q16706 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17