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Showing NP-Card for 8-azabicyclo[3.2.1]octane-1,2,7-triol (NP0249666)

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Record Information
Version2.0
Created at2022-09-07 12:17:00 UTC
Updated at2022-09-07 12:17:01 UTC
NP-MRD IDNP0249666
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-azabicyclo[3.2.1]octane-1,2,7-triol
DescriptionCalystegine A6 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. Calystegine A6 is a very strong basic compound (based on its pKa). Outside of the human body, Calystegine A6 has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and tea. 8-azabicyclo[3.2.1]octane-1,2,7-triol is found in Hyoscyamus niger. This could make calystegine A6 a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)


  Mrv0541 02241214582D          

 11 12  0  0  0  0            999 V2000
   -0.7625    0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039   -0.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211    0.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462   -1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -0.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    1.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066    1.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    0.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    1.7215   -1.7742    0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -0.6955   -0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6298    0.6160    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6074    1.6697    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    1.3179   -0.4164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5458    0.6113    0.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710   -0.7831    0.5755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0204   -1.7118    0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -0.8450   -0.6756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3805   -1.9910   -1.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875    0.3625   -1.4499 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -1.5306    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469   -0.8450   -1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5658    0.9975   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736    0.4185    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    2.0036    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788    2.5957   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2060    2.2373   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083    0.5818    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4507    1.0820    1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885   -0.9958    1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5074   -1.6346    1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0847   -1.9108   -2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    0.2237   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2  9  1  0
  9 10  1  6
  9 11  1  0
  9  7  1  0
 11  5  1  0
  8 22  1  0
  7 21  1  1
  6 19  1  0
  6 20  1  0
  5 18  1  6
  4 16  1  0
  4 17  1  0
  3 14  1  0
  3 15  1  0
  2 13  1  6
  1 12  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)


  Mrv0541 02241214582D          

 11 12  0  0  0  0            999 V2000
   -0.7625    0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039   -0.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211    0.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462   -1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -0.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    1.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066    1.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    0.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249666

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2CCC(O)C1(O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO3/c9-5-2-1-4-3-6(10)7(5,11)8-4/h4-6,8-11H,1-3H2

> <INCHI_KEY>
YOBNKFROEGVQPW-UHFFFAOYSA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.183

> <EXACT_MASS>
159.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.833609584170635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,7-triol

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-1.2294659950000002

> <ALOGPS_LOGS>
0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.045347856504655

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.597638055203074

> <JCHEM_PKA_STRONGEST_BASIC>
9.049900211788795

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
37.863499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.69e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)

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PDB for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)
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  C   UNK     0      -1.423   0.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.423  -1.528   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.039  -2.003   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.941  -0.758   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.039   0.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.580   0.481   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.580  -2.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.668  -0.607   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.170   1.903   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.199   2.003   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.668   0.920   0.000  0.00  0.00           O+0
CONECT    1    2    5   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    6   10                                             
CONECT    6    5    8    9                                                  
CONECT    7    3    8                                                       
CONECT    8    6    7                                                       
CONECT    9    6                                                            
CONECT   10    5                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)
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SMILES for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)
OC1CC2CCC(O)C1(O)N2
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INCHI for NP0249666 (8-azabicyclo[3.2.1]octane-1,2,7-triol)
InChI=1S/C7H13NO3/c9-5-2-1-4-3-6(10)7(5,11)8-4/h4-6,8-11H,1-3H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H13NO3
Average Mass159.1830 Da
Monoisotopic Mass159.08954 Da
IUPAC Name8-azabicyclo[3.2.1]octane-1,2,7-triol
Traditional Name8-azabicyclo[3.2.1]octane-1,2,7-triol
CAS Registry NumberNot Available
SMILES
OC1CC2CCC(O)C1(O)N2
InChI Identifier
InChI=1S/C7H13NO3/c9-5-2-1-4-3-6(10)7(5,11)8-4/h4-6,8-11H,1-3H2
InChI KeyYOBNKFROEGVQPW-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
Hyoscyamus nigerLOTUS 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-1.1ALOGPS
logP-1.2ChemAxon
logS0.62ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.86 m³·mol⁻¹ChemAxon
Polarizability15.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031345  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003409  
KNApSAcK IDC00036864  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85271756  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]