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Showing NP-Card for Swainsonine (NP0137350)

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Record Information
Version2.0
Created at2022-05-30 16:49:45 UTC
Updated at2022-05-30 16:49:45 UTC
NP-MRD IDNP0137350
Secondary Accession NumbersNone
Natural Product Identification
Common NameSwainsonine
DescriptionSwainsonine 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. Swainsonine is a very strong basic compound (based on its pKa). Swainsonine is a potentially toxic compound. Swainsonine inhibits the activity of glycoside hydrolases, especially N-linked glycosylation. It is also an appetite suppressant. Along with slaframine, the other biologially active compound of R. Leguminicola, it may contribute to a condition called "slobbers syndrome" in livestock that has ingested contaminated feed. Other symptoms include diarrhea, lacrimation, stiff joints, frequent urination, tremors, spontaneous abortion, labored breathing, loss of appetite, bloat, and possibly death. Swainsonine also causes vacuolation of most tissues. The major symptom of "slobbers syndrome" is profuse salivation. Swainsonine causes a variety of neurological disorders, including locoism and "slobbers syndrome" in livestock. Swainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). Swainsonine is found in Astragalus allochrous, Astragalus lentiginosus, Astragalus oxyphysus, Castanospermum australe, Ipomoea carnea, Ipomoea polpha, Oxytropis sericea, Slafractonia leguminicola, Swainsona canescens and Swainsona galegifolia. Symptoms of locoism include staggering gait, depression, muscular incoordination, staring, nervousness, hyperexcitability, loss of appetite, and reproductive alterations such as abortion and birth defects.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137350 (Swainsonine)


  Mrv0541 02241205112D          

 12 13  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0137350 (Swainsonine)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.3525    0.3871   -0.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    0.1207    0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5755   -1.1550   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -0.7509   -0.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696   -1.7111   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320   -1.1027    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3917    0.2028   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    1.1160   -0.4386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4177    2.4121   -0.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    0.4798    0.2234 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2581    1.2313    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5226    2.1075    1.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076   -0.4645   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7319    0.0498    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -1.9348    0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0320   -1.5516   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -2.1129   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222   -2.5838    0.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066   -1.8057    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -1.0274    1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166   -0.0012   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463    0.7397    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    1.0466   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774    2.7110   -0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750    0.2642    1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533    1.7585   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950    1.5745    1.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  4  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  6
  9 24  1  0
 10 25  1  1
 11 26  1  6
 12 27  1  0
M  END
Download

3D SDF for NP0137350 (Swainsonine)


  Mrv0541 02241205112D          

 12 13  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CN2CCCC(O)C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2

> <INCHI_KEY>
FXUAIOOAOAVCGD-UHFFFAOYSA-N

> <FORMULA>
C8H15NO3

> <MOLECULAR_WEIGHT>
173.2096

> <EXACT_MASS>
173.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
18.1096065809744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octahydroindolizine-1,2,8-triol

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-1.4067957670000002

> <ALOGPS_LOGS>
0.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.38189835886045

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.284673320768636

> <JCHEM_PKA_STRONGEST_BASIC>
9.470513713136212

> <JCHEM_POLAR_SURFACE_AREA>
63.93000000000001

> <JCHEM_REFRACTIVITY>
43.117799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
octahydroindolizine-1,2,8-triol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0137350 (Swainsonine)

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PDB for NP0137350 (Swainsonine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.590  -0.533   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0137350 (Swainsonine)
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SMILES for NP0137350 (Swainsonine)
OC1CN2CCCC(O)C2C1O
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INCHI for NP0137350 (Swainsonine)
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H15NO3
Average Mass173.2096 Da
Monoisotopic Mass173.10519 Da
IUPAC Nameoctahydroindolizine-1,2,8-triol
Traditional Nameoctahydroindolizine-1,2,8-triol
CAS Registry NumberNot Available
SMILES
OC1CN2CCCC(O)C2C1O
InChI Identifier
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2
InChI KeyFXUAIOOAOAVCGD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Astragalus allochrousLOTUS Database
Astragalus lentiginosusLOTUS Database
Astragalus oxyphysusLOTUS Database
Castanospermum australeLOTUS Database
Ipomoea carneaLOTUS Database
Ipomoea polphaLOTUS Database
Oxytropis sericeaLOTUS Database
Rhizoctonia leguminicolaLOTUS Database
Swainsona canescensLOTUS Database
Swainsona galegifoliaLOTUS Database
Chemical Taxonomy
Description 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
    • 

  • Piperidine
    • 

  • N-alkylpyrrolidine
    • 

  • Pyrrolidine
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Secondary alcohol
    • 

  • 1,2-aminoalcohol
    • 

  • Azacycle
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.12 m³·mol⁻¹ChemAxon
Polarizability18.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSwainsonine  
METLIN IDNot Available
PubChem Compound5363  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available