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Showing NP-Card for Cappariloside B (NP0048086)

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Record Information
Version2.0
Created at2022-03-17 20:50:51 UTC
Updated at2022-03-17 20:50:51 UTC
NP-MRD IDNP0048086
Secondary Accession NumbersNone
Natural Product Identification
Common NameCappariloside B
DescriptionCappariloside B belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Cappariloside B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cappariloside B has been detected, but not quantified in, capers and herbs and spices. This could make cappariloside b a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048086 (Cappariloside B)


  Mrv0541 05061308082D          

 35 38  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23  5  3  0  0  0  0
 24  6  1  0  0  0  0
 24 10  1  0  0  0  0
 25  7  1  0  0  0  0
 26 15  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32  8  1  0  0  0  0
 32 21  1  0  0  0  0
 33 11  1  0  0  0  0
 33 22  1  0  0  0  0
 34 12  1  0  0  0  0
 34 21  1  0  0  0  0
 35 13  1  0  0  0  0
 35 22  1  0  0  0  0
M  END
Download

3D MOL for NP0048086 (Cappariloside B)

Download
3D SDF for NP0048086 (Cappariloside B)

  Mrv0541 05061308082D          

 35 38  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23  5  3  0  0  0  0
 24  6  1  0  0  0  0
 24 10  1  0  0  0  0
 25  7  1  0  0  0  0
 26 15  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32  8  1  0  0  0  0
 32 21  1  0  0  0  0
 33 11  1  0  0  0  0
 33 22  1  0  0  0  0
 34 12  1  0  0  0  0
 34 21  1  0  0  0  0
 35 13  1  0  0  0  0
 35 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2OC(OC3=CC=CC4=C3C(CC#N)=CN4)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O11/c23-5-4-9-6-24-10-2-1-3-11(14(9)10)33-22-20(31)18(29)16(27)13(35-22)8-32-21-19(30)17(28)15(26)12(7-25)34-21/h1-3,6,12-13,15-22,24-31H,4,7-8H2

> <INCHI_KEY>
YWQNATCXFBWYHU-UHFFFAOYSA-N

> <FORMULA>
C22H28N2O11

> <MOLECULAR_WEIGHT>
496.4645

> <EXACT_MASS>
496.169309748

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
47.99426297801376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetonitrile

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-2.5747640956666658

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.419640765734183

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.901574206089986

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
218.10999999999996

> <JCHEM_REFRACTIVITY>
113.96999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048086 (Cappariloside B)
Download
PDB for NP0048086 (Cappariloside B)
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       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.788  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.454 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.788 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.788 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.454  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.166  -2.581   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       4.787 -13.860   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.454 -13.860   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.122 -12.320   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.455  -2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.122  -9.240   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.454  -7.700   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.121 -10.010   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       7.454  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   10                                                       
CONECT    3    1   11                                                       
CONECT    4    5    9                                                       
CONECT    5    4   23                                                       
CONECT    6    9   24                                                       
CONECT    7   12   25                                                       
CONECT    8   13   32                                                       
CONECT    9    4    6   14                                                  
CONECT   10    2   14   24                                                  
CONECT   11    3   14   33                                                  
CONECT   12    7   15   34                                                  
CONECT   13    8   16   35                                                  
CONECT   14    9   10   11                                                  
CONECT   15   12   17   26                                                  
CONECT   16   13   18   27                                                  
CONECT   17   15   19   28                                                  
CONECT   18   16   20   29                                                  
CONECT   19   17   21   30                                                  
CONECT   20   18   22   31                                                  
CONECT   21   19   32   34                                                  
CONECT   22   20   33   35                                                  
CONECT   23    5                                                            
CONECT   24    6   10                                                       
CONECT   25    7                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   20                                                            
CONECT   32    8   21                                                       
CONECT   33   11   22                                                       
CONECT   34   12   21                                                       
CONECT   35   13   22                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

Download
3D PDB for NP0048086 (Cappariloside B)
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SMILES for NP0048086 (Cappariloside B)
OCC1OC(OCC2OC(OC3=CC=CC4=C3C(CC#N)=CN4)C(O)C(O)C2O)C(O)C(O)C1O
Download
INCHI for NP0048086 (Cappariloside B)
InChI=1S/C22H28N2O11/c23-5-4-9-6-24-10-2-1-3-11(14(9)10)33-22-20(31)18(29)16(27)13(35-22)8-32-21-19(30)17(28)15(26)12(7-25)34-21/h1-3,6,12-13,15-22,24-31H,4,7-8H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H28N2O11
Average Mass496.4645 Da
Monoisotopic Mass496.16931 Da
IUPAC Name2-(4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetonitrile
Traditional Name2-(4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetonitrile
CAS Registry Number229483-42-5
SMILES
OCC1OC(OCC2OC(OC3=CC=CC4=C3C(CC#N)=CN4)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C22H28N2O11/c23-5-4-9-6-24-10-2-1-3-11(14(9)10)33-22-20(31)18(29)16(27)13(35-22)8-32-21-19(30)17(28)15(26)12(7-25)34-21/h1-3,6,12-13,15-22,24-31H,4,7-8H2
InChI KeyYWQNATCXFBWYHU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Capparis spinosaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentPhenolic glycosides  
Alternative Parents
Substituents
  • Phenolic glycoside
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  • Disaccharide
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  • O-glycosyl compound
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  • 3-alkylindole
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  • Indole
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  • Indole or derivatives
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  • Oxane
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  • Benzenoid
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  • Substituted pyrrole
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  • Heteroaromatic compound
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  • Pyrrole
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  • Secondary alcohol
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  • Acetal
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  • Carbonitrile
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  • Nitrile
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  • Oxacycle
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  • Azacycle
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  • Polyol
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  • Organoheterocyclic compound
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  • Organic nitrogen compound
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  • Organonitrogen compound
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  • Organopnictogen compound
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  • Hydrocarbon derivative
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  • Primary alcohol
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  • Alcohol
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  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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-0.68ALOGPS
logP-2.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)11.9ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area218.11 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity113.97 m³·mol⁻¹ChemAxon
Polarizability47.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0034938  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013530  
KNApSAcK IDC00026884  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73157716  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available