NP-MRD: Showing NP-Card for asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside (NP0028023)

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Record Information

Version

2.0

Created at

2021-06-19 20:01:29 UTC

Updated at

2021-06-29 23:54:32 UTC

NP-MRD ID

NP0028023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside

Provided By

JEOL Database JEOL Logo

Description

asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside is found in Pieris japonica. asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside was first documented in 2005 (PMID: 15787442). Based on a literature review very few articles have been published on Asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122013D          

 56 58  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192122013D          

 56 58  0  0  0  0            999 V2000
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   -0.2031   -1.2725   -3.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.9883    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.4154    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9729   -4.1625   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436   -2.4479   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.8636    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    3.1007   -0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    2.1633   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.6554    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    0.3693   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    2.1061    2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267    4.4893    2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    1.9137    3.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350    4.1538    3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    2.3139    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 19  1  0  0  0  0
 15 16  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
 19 20  1  0  0  0  0
 10 11  1  0  0  0  0
 19  7  2  0  0  0  0
 11 12  1  0  0  0  0
  3 32  2  0  0  0  0
 12 13  2  0  0  0  0
  7  5  1  0  0  0  0
 13 14  1  0  0  0  0
  5  4  2  0  0  0  0
 14 15  2  0  0  0  0
 21 30  1  0  0  0  0
 30 28  1  0  0  0  0
 28 26  1  0  0  0  0
 26 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 26 27  1  0  0  0  0
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  4  3  1  0  0  0  0
 24 25  1  0  0  0  0
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  7  8  1  0  0  0  0
  5  6  1  0  0  0  0
 17 18  2  0  0  0  0
  3  2  1  0  0  0  0
 18 12  1  0  0  0  0
  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
 21 20  1  0  0  0  0
  4 36  1  0  0  0  0
 32 56  1  0  0  0  0
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 30 54  1  1  0  0  0
 31 55  1  0  0  0  0
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 23 48  1  6  0  0  0
 25 51  1  0  0  0  0
  6 37  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C(=O)C1=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])C(=O)[C@@]2([H])O[H])C([H])=C(OC([H])([H])[H])C([H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19,21-24,26-27,29H,4,7,10H2,1H3/t17-,19-,21-,22-/m1/s1

> <INCHI_KEY>
NTMBWMBWUUMBLE-JHMKDJTOSA-N

> <FORMULA>
C22H24O10

> <MOLECULAR_WEIGHT>
448.424

> <EXACT_MASS>
448.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.57797369155427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,5R,6R)-3,5-dihydroxy-2-{3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy}-6-(hydroxymethyl)oxan-4-one

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.738542669666666

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.629034123157428

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.929359292987762

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9866476467653875

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
109.5673

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,5R,6R)-3,5-dihydroxy-2-{3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy}-6-(hydroxymethyl)oxan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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   -1.6949    0.8704   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876    1.1079    1.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154    2.0764    0.9292 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0844    1.4015    0.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1759    2.3120    0.3422 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3239    1.5321   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9313    1.0717   -1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5831    2.8917    1.6949 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6178    3.8532    1.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3475    3.5153    2.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    4.6001    2.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0661    2.6941    2.3229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0517    3.5140    2.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147    1.6106   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854    2.4866   -4.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1017    0.4683   -3.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -1.2725   -3.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.9883    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.4154    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -1.6998    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936   -2.8927    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6125   -6.5072   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -6.1382   -3.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9729   -4.1625   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436   -2.4479   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.8636    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    3.1007   -0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    2.1633   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.6554    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    0.3693   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    2.1061    2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267    4.4893    2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    1.9137    3.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350    4.1538    3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    2.3139    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 19  1  0
 15 16  1  0
  8 10  1  0
  8  9  2  0
 19 20  1  0
 10 11  1  0
 19  7  2  0
 11 12  1  0
  3 32  2  0
 12 13  2  0
  7  5  1  0
 13 14  1  0
  5  4  2  0
 14 15  2  0
 21 30  1  0
 30 28  1  0
 28 26  1  0
 26 23  1  0
 23 22  1  0
 22 21  1  0
 26 27  1  0
 30 31  1  0
  4  3  1  0
 24 25  1  0
 15 17  1  0
 28 29  2  0
  7  8  1  0
  5  6  1  0
 17 18  2  0
  3  2  1  0
 18 12  1  0
  2  1  1  0
 23 24  1  0
 21 20  1  0
  4 36  1  0
 32 56  1  0
 10 38  1  0
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 11 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 17 45  1  0
 18 46  1  0
 16 44  1  0
 21 47  1  6
 26 52  1  1
 27 53  1  0
 30 54  1  1
 31 55  1  0
 24 49  1  0
 24 50  1  0
 23 48  1  6
 25 51  1  0
  6 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.001   2.170  -3.481  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.433   2.260  -2.180  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.345   1.473  -1.925  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.742   0.592  -2.823  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.636  -0.162  -2.424  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.091  -0.989  -3.371  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.133  -0.066  -1.121  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.018  -0.953  -0.722  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.928  -1.064  -1.507  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.051  -1.690   0.606  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.364  -2.415   0.902  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.705  -3.482  -0.111  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.918  -4.638  -0.221  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.226  -5.615  -1.169  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.319  -5.441  -2.008  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.580  -6.417  -2.923  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.117  -4.307  -1.910  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.811  -3.331  -0.959  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.695   0.870  -0.249  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.188   1.108   1.003  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.115   2.076   0.929  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.084   1.401   0.537  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.176   2.312   0.342  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.324   1.532  -0.309  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.931   1.072  -1.602  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.583   2.892   1.695  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.618   3.853   1.545  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.347   3.515   2.332  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.410   4.600   2.921  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.066   2.694   2.323  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.052   3.514   2.669  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.815   1.611  -0.639  0.00  0.00           C+0
HETATM   33  H   UNK     0      -4.285   2.487  -4.247  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.374   1.160  -3.680  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.855   2.854  -3.521  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.102   0.468  -3.839  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.203  -1.272  -3.061  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.183  -0.988   1.412  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.772  -2.415   0.591  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.191  -1.700   0.983  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.294  -2.893   1.888  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.059  -4.787   0.428  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.613  -6.507  -1.254  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.338  -6.138  -3.461  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.973  -4.162  -2.561  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.444  -2.448  -0.891  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.367   2.864   0.203  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.861   3.101  -0.354  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.208   2.163  -0.438  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.601   0.655   0.286  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.257   0.369  -1.475  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.930   2.106   2.376  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.527   4.489   2.284  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.162   1.914   3.086  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.735   4.154   3.338  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.269   2.314   0.057  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1                                                       
CONECT    3   32    4    2                                                  
CONECT    4    5    3   36                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   37                                                       
CONECT    7   19    5    8                                                  
CONECT    8   10    9    7                                                  
CONECT    9    8                                                            
CONECT   10    8   11   38   39                                             
CONECT   11   10   12   40   41                                             
CONECT   12   11   13   18                                                  
CONECT   13   12   14   42                                                  
CONECT   14   13   15   43                                                  
CONECT   15   16   14   17                                                  
CONECT   16   15   44                                                       
CONECT   17   15   18   45                                                  
CONECT   18   17   12   46                                                  
CONECT   19   32   20    7                                                  
CONECT   20   19   21                                                       
CONECT   21   30   22   20   47                                             
CONECT   22   23   21                                                       
CONECT   23   26   22   24   48                                             
CONECT   24   25   23   49   50                                             
CONECT   25   24   51                                                       
CONECT   26   28   23   27   52                                             
CONECT   27   26   53                                                       
CONECT   28   30   26   29                                                  
CONECT   29   28                                                            
CONECT   30   21   28   31   54                                             
CONECT   31   30   55                                                       
CONECT   32   19    3   56                                                  
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   21                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
CONECT   56   32                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -5.0013    2.1703   -3.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4326    2.2605   -2.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3446    1.4726   -1.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417    0.5917   -2.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -0.1617   -2.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0913   -0.9888   -3.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329   -0.0659   -1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -0.9533   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -1.0637   -1.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -1.6899    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641   -2.4150    0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7047   -3.4819   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -4.6378   -0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -5.6150   -1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -5.4410   -2.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796   -6.4172   -2.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166   -4.3066   -1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8114   -3.3308   -0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949    0.8704   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876    1.1079    1.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154    2.0764    0.9292 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0844    1.4015    0.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1759    2.3120    0.3422 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3239    1.5321   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9313    1.0717   -1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5831    2.8917    1.6949 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6178    3.8532    1.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3475    3.5153    2.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    4.6001    2.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0661    2.6941    2.3229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0517    3.5140    2.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147    1.6106   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854    2.4866   -4.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3738    1.1599   -3.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8549    2.8538   -3.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017    0.4683   -3.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -1.2725   -3.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -0.9883    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.4154    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -1.6998    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936   -2.8927    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589   -4.7873    0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -6.5072   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -6.1382   -3.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9729   -4.1625   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436   -2.4479   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.8636    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    3.1007   -0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    2.1633   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.6554    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    0.3693   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    2.1061    2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267    4.4893    2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    1.9137    3.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350    4.1538    3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    2.3139    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 19  1  0
 15 16  1  0
  8 10  1  0
  8  9  2  0
 19 20  1  0
 10 11  1  0
 19  7  2  0
 11 12  1  0
  3 32  2  0
 12 13  2  0
  7  5  1  0
 13 14  1  0
  5  4  2  0
 14 15  2  0
 21 30  1  0
 30 28  1  0
 28 26  1  0
 26 23  1  0
 23 22  1  0
 22 21  1  0
 26 27  1  0
 30 31  1  0
  4  3  1  0
 24 25  1  0
 15 17  1  0
 28 29  2  0
  7  8  1  0
  5  6  1  0
 17 18  2  0
  3  2  1  0
 18 12  1  0
  2  1  1  0
 23 24  1  0
 21 20  1  0
  4 36  1  0
 32 56  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 17 45  1  0
 18 46  1  0
 16 44  1  0
 21 47  1  6
 26 52  1  1
 27 53  1  0
 30 54  1  1
 31 55  1  0
 24 49  1  0
 24 50  1  0
 23 48  1  6
 25 51  1  0
  6 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
Asebogenin 2'-O-b-D-ribohexo-3-ulopyranoside	Generator
Asebogenin 2'-O-β-D-ribohexo-3-ulopyranoside	Generator

Chemical Formula

C₂₂H₂₄O₁₀

Average Mass

448.4240 Da

Monoisotopic Mass

448.13695 Da

IUPAC Name

(2S,3S,5R,6R)-3,5-dihydroxy-2-{3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy}-6-(hydroxymethyl)oxan-4-one

Traditional Name

(2S,3S,5R,6R)-3,5-dihydroxy-2-{3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy}-6-(hydroxymethyl)oxan-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C(=O)C1=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])C(=O)[C@@]2([H])O[H])C([H])=C(OC([H])([H])[H])C([H])=C1O[H]

InChI Identifier

InChI=1S/C22H24O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19,21-24,26-27,29H,4,7,10H2,1H3/t17-,19-,21-,22-/m1/s1

InChI Key

NTMBWMBWUUMBLE-JHMKDJTOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pieris japonica	JEOL database	Yao, G.-M., et al, J. Nat. Prod. 68, 392 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Alkyl-phenylketone
Hexose monosaccharide
Butyrophenone
Methoxyphenol
Phenylketone
Methoxybenzene
Benzoyl
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Vinylogous acid
Ketone
Cyclic ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.49	ALOGPS
logP	1.74	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.57 m³·mol⁻¹	ChemAxon
Polarizability	43.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9422898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11247865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yao GM, Ding Y, Zuo JP, Wang HB, Wang YB, Ding BY, Chiu P, Qin GW: Dihydrochalcones from the leaves of Pieris japonica. J Nat Prod. 2005 Mar;68(3):392-6. doi: 10.1021/np049698a. [PubMed:15787442 ]
Yao, G.-M., et al. (2005). Yao, G.-M., et al, J. Nat. Prod. 68, 392 (2005). J. Nat. Prod..

Showing NP-Card for asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside (NP0028023)

MOL for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

3D MOL for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

3D SDF for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

3D-SDF for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

PDB for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

3D PDB for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

SMILES for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

INCHI for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

Structure for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)

3D Structure for NP0028023 (asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside)