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Showing NP-Card for Calystegine B2 (NP0049170)

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Record Information
Version2.0
Created at2022-03-17 21:08:13 UTC
Updated at2022-03-17 21:08:13 UTC
NP-MRD IDNP0049170
Secondary Accession NumbersNone
Natural Product Identification
Common NameCalystegine B2
DescriptionCalystegine B2, also known as nortropanoline or calystegine b(4), 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 B2 is a very strong basic compound (based on its pKa). Outside of the human body, Calystegine B2 has been detected, but not quantified in, several different foods, such as alcoholic beverages, eggplants, fruits, potato, and swamp cabbages. Calystegine B2 is found in Argyreia capitata, Argyreia hookeri Clarke, Atropa belladonna , Bonamia semidigyna, Bonamia spectabilis, Brunfelsia nitida, Calystegia japonica Choisy , Calystegia sepium , Calystegia soldanella (L.) Roem.et Schult. , Convolvulus arvensis L , Convolvulus caput-medusae Lowe, Convolvulus cneorum L., Convolvulus sabatius ssp.mauritanicus, Convolvulus spp., Datura wrightii, Dichondra repens , Duboisia leichhardtii, Duboisia leichhardtii F.Muell, Erycibe malaccensis, Erycibe parvifolia, Erythroxylum novogranatense, Evolvulus argyreus, Falkia repens L., Hyoscyamus albus , Hyoscyamus niger , Ipomoea alba , Ipomoea batatas , Ipomoea batatas Lam.var.edulis Makino , Ipomoea carnea, Ipomoea carnea Jacq. , Ipomoea eremnobracha, Ipomoea hederifolia, Ipomoea obscura Ker. , Ipomoea pes-caprae (L.) Sweet , Ipomoea setifera , Iseia luxurians, Lycium chinense , Mandragora autumnalis , Mandragora officinarum, Mandragora officinarum L. , Maripa panamensis, Merremia quinquefolia , Merremia umbellata , Morus alba, Morus australis, Physalis alkekengi , Physalis alkekengi var.francheti , Physalis lagascae, Porana volubilis, Quamoclit angulata Bojer., Scopolia japonica , Solanum dimidiatum, Solanum dulcamara , Solanum kwebense, Solanum sodomaeum, Stictocardia campanulata, Turbina abutiloides, Withania frutescens and Withania somnifera . This could make calystegine B2 a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049170 (Calystegine B2)


  Mrv0541 05061310322D          

 12 13  0  0  0  0            999 V2000
    0.7292   -1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450   -0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -1.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5877   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -0.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228   -0.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
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3D MOL for NP0049170 (Calystegine B2)

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3D SDF for NP0049170 (Calystegine B2)

  Mrv0541 05061310322D          

 12 13  0  0  0  0            999 V2000
    0.7292   -1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450   -0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -1.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5877   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -0.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228   -0.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C2CCC(O)(N2)C(O)C1O

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

> <INCHI_KEY>
FXFBVZOJVHCEDO-UHFFFAOYSA-N

> <FORMULA>
C7H13NO4

> <MOLECULAR_WEIGHT>
175.1824

> <EXACT_MASS>
175.084457909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.31541680506856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol

> <ALOGPS_LOGP>
-1.81

> <JCHEM_LOGP>
-2.148462142

> <ALOGPS_LOGS>
0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.075446024332724

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.129613675619893

> <JCHEM_PKA_STRONGEST_BASIC>
8.572879603048014

> <JCHEM_POLAR_SURFACE_AREA>
92.95

> <JCHEM_REFRACTIVITY>
39.071

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049170 (Calystegine B2)
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PDB for NP0049170 (Calystegine B2)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.361  -2.328   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.220  -3.021   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.951  -1.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.659  -0.996   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.913  -2.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.964  -1.711   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.176  -1.711   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.071  -0.064   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       5.204  -0.442   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.897  -3.704   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.048   0.075   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.416  -1.199   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    2    6    8   12                                             
CONECT    8    3    7                                                       
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0049170 (Calystegine B2)
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SMILES for NP0049170 (Calystegine B2)
OC1C2CCC(O)(N2)C(O)C1O
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INCHI for NP0049170 (Calystegine B2)
InChI=1S/C7H13NO4/c9-4-3-1-2-7(12,8-3)6(11)5(4)10/h3-6,8-12H,1-2H2
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View in JSmol
Synonyms
ValueSource
Calystegin b2HMDB
NortropanolineHMDB
Calystegine b(4)MeSH
Calystegine b(2)MeSH
Calystegine b4MeSH
1,2,3,4-Tetrahydroxy-nor-tropaneMeSH
Calystegine b3MeSH
Calystegine b(3)MeSH
Chemical FormulaC7H13NO4
Average Mass175.1824 Da
Monoisotopic Mass175.08446 Da
IUPAC Name8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol
Traditional Name8-azabicyclo[3.2.1]octane-1,2,3,4-tetrol
CAS Registry Number127414-85-1
SMILES
OC1C2CCC(O)(N2)C(O)C1O
InChI Identifier
InChI=1S/C7H13NO4/c9-4-3-1-2-7(12,8-3)6(11)5(4)10/h3-6,8-12H,1-2H2
InChI KeyFXFBVZOJVHCEDO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Argyreia capitataPlant
Argyreia hookeri ClarkePlant
Atropa belladonnaPlant
Bonamia semidigynaPlant
Bonamia spectabilisPlant
Brunfelsia nitidaPlant
Calystegia japonica ChoisyPlant
Calystegia sepiumPlant
Calystegia soldanella (L.) Roem.et Schult.Plant
Convolvulus arvensis LPlant
Convolvulus caput-medusae LowePlant
Convolvulus cneorumPlant
Convolvulus sabatius ssp.mauritanicusPlant
Convolvulus spp.Plant
Datura wrightiiPlant
Dichondra repensPlant
Duboisia leichhardtiiPlant
Duboisia leichhardtii F.MuellPlant
Erycibe malaccensisPlant
Erycibe parvifoliaPlant
Erythroxylum novogranatensePlant
Evolvulus argyreusPlant
Falkia repens L.Plant
Hyoscyamus albusPlant
Hyoscyamus nigerPlant
Ipomoea albaPlant
Ipomoea aquaticaFooDB
Ipomoea batatasPlant
Ipomoea batatas Lam.var.edulis MakinoPlant
Ipomoea carneaLOTUS Database
Ipomoea carnea Jacq.Plant
Ipomoea eremnobrachaPlant
Ipomoea hederifoliaPlant
Ipomoea obscura Ker.Plant
Ipomoea pes-caprae (L.) SweetPlant
Ipomoea setiferaPlant
Iseia luxuriansPlant
Lycium chinensePlant
Mandragora autumnalisPlant
Mandragora officinarumLOTUS Database
Mandragora officinarum L.Plant
Maripa panamensisPlant
Merremia quinquefoliaPlant
Merremia umbellataPlant
Morus albaLOTUS Database
Morus australisLOTUS Database
Physalis alkekengiPlant
Physalis alkekengi var.franchetiPlant
Physalis lagascaeLOTUS Database
Porana volubilisPlant
Quamoclit angulata Bojer.Plant
Scopolia japonicaPlant
Solanum dimidiatumPlant
Solanum dulcamaraPlant
Solanum kwebensePlant
Solanum melongenaFooDB
Solanum sodomaeumPlant
Solanum tuberosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Stictocardia campanulataPlant
Turbina abutiloidesPlant
Withania frutescensPlant
Withania somniferaPlant
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-1.8ALOGPS
logP-2.1ChemAxon
logS0.62ALOGPS
pKa (Strongest Acidic)12.13ChemAxon
pKa (Strongest Basic)8.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area92.95 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.07 m³·mol⁻¹ChemAxon
Polarizability16.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038594  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017985  
KNApSAcK IDC00002283  
Chemspider ID21537476  
KEGG Compound IDC10851  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3693124  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available