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Showing NP-Card for 8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol (NP0293229)

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Record Information
Version2.0
Created at2022-09-10 01:08:06 UTC
Updated at2022-09-10 01:08:07 UTC
NP-MRD IDNP0293229
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol
DescriptionCalystegine B1 belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. 8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol is found in Calystegia sepium, Duboisia leichhardtii, Hyoscyamus niger, Ipomoea carnea and Physalis minima. Calystegine B1 is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)


  Mrv1533004231514482D          

 12 13  0  0  0  0            999 V2000
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 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 NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.4220   -0.5237   -1.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1087    0.0503 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1514    1.2458   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    0.9963    0.4632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7702    2.0417    1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -0.1304    1.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7003   -1.0351    0.5237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1664   -1.5598   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -0.8023   -0.5817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0906   -0.9242    0.6866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1190    0.6740   -0.7116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2217    1.4968   -0.7346 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3790   -0.7772   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683   -0.0389    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072    2.0053    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    1.6115   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698    2.7442    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    0.2122    2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.8295    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -2.6218   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026   -1.4747   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -1.1382   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -1.8842    0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652    0.7622   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.0587   -0.3876 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  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
  7  2  1  0
 11  4  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  8 21  1  0
  9 22  1  6
 10 23  1  0
 11 24  1  6
 12 25  1  0
M  END
Download

3D SDF for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)


  Mrv1533004231514482D          

 12 13  0  0  0  0            999 V2000
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2(O)NC1CC(O)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO4/c9-4-1-3-5(10)2-7(12,8-3)6(4)11/h3-6,8-12H,1-2H2

> <INCHI_KEY>
BQFFLYRIKODYEN-UHFFFAOYSA-N

> <FORMULA>
C7H13NO4

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.084457903

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.635269350179648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol

> <ALOGPS_LOGP>
-1.91

> <JCHEM_LOGP>
-2.166820226

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.523821953270442

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.169415574231907

> <JCHEM_PKA_STRONGEST_BASIC>
8.47796595124574

> <JCHEM_POLAR_SURFACE_AREA>
92.95

> <JCHEM_REFRACTIVITY>
38.767799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)

Download
PDB for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.692  -2.044   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.443   2.626   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.496  -1.404   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    6    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 NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)
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SMILES for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)
OC1CC2(O)NC1CC(O)C2O
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INCHI for NP0293229 (8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol)
InChI=1S/C7H13NO4/c9-4-1-3-5(10)2-7(12,8-3)6(4)11/h3-6,8-12H,1-2H2
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View in JSmol
Synonyms
ValueSource
Calystegine b(1)MeSH
Chemical FormulaC7H13NO4
Average Mass175.1840 Da
Monoisotopic Mass175.08446 Da
IUPAC Name8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol
Traditional Name8-azabicyclo[3.2.1]octane-1,2,3,6-tetrol
CAS Registry NumberNot Available
SMILES
OC1CC2(O)NC1CC(O)C2O
InChI Identifier
InChI=1S/C7H13NO4/c9-4-1-3-5(10)2-7(12,8-3)6(4)11/h3-6,8-12H,1-2H2
InChI KeyBQFFLYRIKODYEN-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
Calystegia sepiumLOTUS Database
Duboisia leichhardtiiLOTUS Database
Hyoscyamus nigerLOTUS Database
Ipomoea carneaLOTUS Database
Physalis minimaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassTropane alkaloids  
Sub ClassNot Available
Direct ParentTropane alkaloids  
Alternative Parents
Substituents
  • Tropane alkaloid
    • 

  • Piperidine
    • 

  • Cyclic alcohol
    • 

  • Pyrrolidine
    • 

  • Hemiaminal
    • 

  • Secondary alcohol
    • 

  • Alkanolamine
    • 

  • Secondary aliphatic amine
    • 

  • Polyol
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • Organic nitrogen 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-1.9ALOGPS
logP-2.2ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)8.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area92.95 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.77 m³·mol⁻¹ChemAxon
Polarizability16.64 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 LinkNot Available
METLIN IDNot Available
PubChem Compound3804328  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]