NP-MRD: Showing NP-Card for kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside) (NP0027403)

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Record Information

Version

2.0

Created at

2021-06-19 19:34:20 UTC

Updated at

2021-06-29 23:53:30 UTC

NP-MRD ID

NP0027403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside)

Provided By

JEOL Database JEOL Logo

Description

CHEMBL469851 is also known as karp CPD. kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside) is found in Zingiber aromaticum and Zingiber spectabile. kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside) was first documented in 2004 (Usia, T., et al.). Based on a literature review very few articles have been published on CHEMBL469851.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121343D          

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     RDKit          3D

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  Mrv1652306192121343D          

 61 64  0  0  0  0            999 V2000
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    0.0750   -0.2138   -5.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    0.3087   -6.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185   -1.3313   -5.5537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    5.0219   -3.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0863    1.0424   -1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    1.5294   -0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -0.2051   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -0.8996   -2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -3.3078   -4.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477   -3.8050   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -3.1333   -1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -1.3072    3.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -0.2634    6.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1672    0.7320    3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645   -0.9032   -2.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4500   -0.2093   -4.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2929    1.4716   -3.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8536    0.2299   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745    1.4541   -4.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0941   -0.7206   -3.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.5980   -5.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.1598   -6.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -0.4779   -7.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0  0  0  0
 25 26  1  0  0  0  0
 26  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 17  1  0  0  0  0
 33 34  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 33 31  1  0  0  0  0
 12 13  2  0  0  0  0
 20 22  2  0  0  0  0
 13 15  1  0  0  0  0
 33  5  1  0  0  0  0
 15 16  2  0  0  0  0
 16 10  1  0  0  0  0
  9 10  1  0  0  0  0
 22 23  1  0  0  0  0
 13 14  1  0  0  0  0
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 26 27  2  0  0  0  0
  6  5  1  0  0  0  0
 20 21  1  0  0  0  0
 18 19  2  0  0  0  0
 23 24  1  0  0  0  0
  8  7  1  0  0  0  0
 19 20  1  0  0  0  0
  4  2  1  0  0  0  0
 18 25  1  0  0  0  0
  2  1  1  0  0  0  0
  6 28  1  0  0  0  0
  2  3  2  0  0  0  0
 28 29  1  0  0  0  0
 34 35  1  0  0  0  0
 29 31  1  0  0  0  0
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  6  7  1  0  0  0  0
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  5  4  1  0  0  0  0
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  6 42  1  1  0  0  0
 30 53  1  0  0  0  0
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 30 55  1  0  0  0  0
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  1 40  1  0  0  0  0
 36 59  1  0  0  0  0
 36 60  1  0  0  0  0
 36 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C(O[C@]2([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])OC(=O)C([H])([H])[H])C(=O)C2=C(O[H])C([H])=C(O[H])C([H])=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c1-10-19(31)22(34-11(2)26)24(35-12(3)27)25(33-10)37-23-20(32)18-16(30)8-15(29)9-17(18)36-21(23)13-4-6-14(28)7-5-13/h4-10,19,22,24-25,28-31H,1-3H3/t10-,19-,22+,24+,25-/m0/s1

> <INCHI_KEY>
BHCRVKVXJRBQJR-YPDHAKIYSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.57992280720717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6S)-4-(acetyloxy)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-6-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.087890813000001

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.869718923765357

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372346199475972

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6277091271996467

> <JCHEM_POLAR_SURFACE_AREA>
178.27999999999997

> <JCHEM_REFRACTIVITY>
124.05389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6S)-4-(acetyloxy)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -0.9427    4.8824   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0370   -1.1195    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -1.6046   -0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9208   -0.9989   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5371   -1.3839   -2.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0750   -0.2138   -5.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    0.3087   -6.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185   -1.3313   -5.5537 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4541   -0.8996   -2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -3.3078   -4.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477   -3.8050   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -3.1333   -1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -1.3072    3.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -0.2634    6.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6645   -0.9032   -2.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4500   -0.2093   -4.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2139   -1.0580   -5.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -0.7206   -3.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.5980   -5.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.1598   -6.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -0.4779   -7.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 25 26  1  0
 26  8  1  0
  8  9  2  0
  9 17  1  0
 33 34  1  0
 10 11  2  0
 11 12  1  0
 33 31  1  0
 12 13  2  0
 20 22  2  0
 13 15  1  0
 33  5  1  0
 15 16  2  0
 16 10  1  0
  9 10  1  0
 22 23  1  0
 13 14  1  0
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  6  5  1  0
 20 21  1  0
 18 19  2  0
 23 24  1  0
  8  7  1  0
 19 20  1  0
  4  2  1  0
 18 25  1  0
  2  1  1  0
  6 28  1  0
  2  3  2  0
 28 29  1  0
 34 35  1  0
 29 31  1  0
 35 36  1  0
  6  7  1  0
 35 37  2  0
 31 32  1  0
 29 30  1  0
  5  4  1  0
 32 57  1  0
 31 56  1  6
  6 42  1  1
 30 53  1  0
 30 54  1  0
 30 55  1  0
 29 52  1  1
  5 41  1  1
 33 58  1  1
 22 50  1  0
 19 48  1  0
 11 43  1  0
 12 44  1  0
 15 46  1  0
 16 47  1  0
 14 45  1  0
 21 49  1  0
 24 51  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 36 59  1  0
 36 60  1  0
 36 61  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      -0.943   4.882  -2.305  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.739   3.482  -1.817  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.199   3.181  -0.763  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.243   2.592  -2.714  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.105   1.200  -2.333  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.162   0.818  -1.274  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.948  -0.527  -0.818  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.201  -0.589   0.349  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.037  -1.119   0.398  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.723  -1.605  -0.812  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.921  -0.999  -1.220  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.537  -1.384  -2.412  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.962  -2.378  -3.192  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.562  -2.682  -4.378  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.798  -3.022  -2.785  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.182  -2.638  -1.591  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.818  -1.209   1.537  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.294  -0.775   2.726  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.104  -0.890   3.855  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.624  -0.467   5.091  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.449  -0.598   6.169  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.654   0.069   5.219  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.459   0.181   4.088  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.706   0.714   4.273  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.986  -0.239   2.839  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.809  -0.131   1.628  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.946   0.325   1.697  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.478   0.967  -1.833  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.724   0.154  -2.984  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.161   0.421  -3.424  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.725   0.442  -4.122  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.980  -0.458  -5.208  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.290   0.323  -3.580  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.307   0.731  -4.564  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.075  -0.214  -5.463  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.172   0.309  -6.337  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.419  -1.331  -5.554  0.00  0.00           O+0
HETATM   38  H   UNK     0      -0.425   5.022  -3.258  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.011   5.085  -2.414  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.527   5.584  -1.577  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.086   1.042  -1.962  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.134   1.529  -0.443  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.369  -0.205  -0.625  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.454  -0.900  -2.736  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.991  -3.308  -4.858  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.348  -3.805  -3.388  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.738  -3.133  -1.288  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.104  -1.307   3.776  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.990  -0.263   6.958  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.038   0.401   6.179  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.167   0.732   3.403  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.664  -0.903  -2.694  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.450  -0.209  -4.270  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.293   1.472  -3.707  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.854   0.230  -2.597  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.874   1.454  -4.516  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.214  -1.058  -5.323  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.094  -0.721  -3.309  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.028   0.598  -5.723  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.809   1.160  -6.918  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.490  -0.478  -7.027  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5   33    6    4   41                                             
CONECT    6    5   28    7   42                                             
CONECT    7    8    6                                                       
CONECT    8   26    9    7                                                  
CONECT    9    8   17   10                                                  
CONECT   10   11   16    9                                                  
CONECT   11   10   12   43                                                  
CONECT   12   11   13   44                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13   45                                                       
CONECT   15   13   16   46                                                  
CONECT   16   15   10   47                                                  
CONECT   17   18    9                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   48                                                  
CONECT   20   22   21   19                                                  
CONECT   21   20   49                                                       
CONECT   22   20   23   50                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   51                                                       
CONECT   25   26   23   18                                                  
CONECT   26   25    8   27                                                  
CONECT   27   26                                                            
CONECT   28    6   29                                                       
CONECT   29   28   31   30   52                                             
CONECT   30   29   53   54   55                                             
CONECT   31   33   29   32   56                                             
CONECT   32   31   57                                                       
CONECT   33   34   31    5   58                                             
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   59   60   61                                             
CONECT   37   35                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   30                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
CONECT   59   36                                                            
CONECT   60   36                                                            
CONECT   61   36                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
   -0.9427    4.8824   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390    3.4821   -1.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1988    3.1810   -0.7625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    2.5918   -2.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    1.2000   -2.3328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1618    0.8178   -1.2742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9476   -0.5269   -0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2012   -0.5888    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -1.1195    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -1.6046   -0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9208   -0.9989   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5371   -1.3839   -2.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -2.3783   -3.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -2.6824   -4.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7982   -3.0223   -2.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818   -2.6377   -1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8177   -1.2091    1.5370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2935   -0.7746    2.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -0.8900    3.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -0.4672    5.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488   -0.5977    6.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    0.0688    5.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.1812    4.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064    0.7139    4.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   -0.2390    2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8086   -0.1307    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463    0.3254    1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4780    0.9666   -1.8331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    0.1541   -2.9837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1607    0.4214   -3.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7250    0.4415   -4.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9800   -0.4584   -5.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2895    0.3226   -3.5796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3066    0.7314   -4.5637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -0.2138   -5.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    0.3087   -6.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185   -1.3313   -5.5537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    5.0219   -3.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    5.0848   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267    5.5839   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863    1.0424   -1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    1.5294   -0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -0.2051   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -0.8996   -2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -3.3078   -4.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477   -3.8050   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -3.1333   -1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -1.3072    3.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -0.2634    6.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378    0.4006    6.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1672    0.7320    3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645   -0.9032   -2.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4500   -0.2093   -4.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2929    1.4716   -3.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8536    0.2299   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745    1.4541   -4.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -1.0580   -5.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -0.7206   -3.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    0.5980   -5.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.1598   -6.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -0.4779   -7.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 25 26  1  0
 26  8  1  0
  8  9  2  0
  9 17  1  0
 33 34  1  0
 10 11  2  0
 11 12  1  0
 33 31  1  0
 12 13  2  0
 20 22  2  0
 13 15  1  0
 33  5  1  0
 15 16  2  0
 16 10  1  0
  9 10  1  0
 22 23  1  0
 13 14  1  0
 23 25  2  0
 26 27  2  0
  6  5  1  0
 20 21  1  0
 18 19  2  0
 23 24  1  0
  8  7  1  0
 19 20  1  0
  4  2  1  0
 18 25  1  0
  2  1  1  0
  6 28  1  0
  2  3  2  0
 28 29  1  0
 34 35  1  0
 29 31  1  0
 35 36  1  0
  6  7  1  0
 35 37  2  0
 31 32  1  0
 29 30  1  0
  5  4  1  0
 32 57  1  0
 31 56  1  6
  6 42  1  1
 30 53  1  0
 30 54  1  0
 30 55  1  0
 29 52  1  1
  5 41  1  1
 33 58  1  1
 22 50  1  0
 19 48  1  0
 11 43  1  0
 12 44  1  0
 15 46  1  0
 16 47  1  0
 14 45  1  0
 21 49  1  0
 24 51  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 36 59  1  0
 36 60  1  0
 36 61  1  0
M  END

View in JSmol

Synonyms

Value	Source
Kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside)	MeSH
KARP CPD	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

(2S,3R,4R,5S,6S)-4-(acetyloxy)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-6-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4R,5S,6S)-4-(acetyloxy)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C(O[C@]2([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])OC(=O)C([H])([H])[H])C(=O)C2=C(O[H])C([H])=C(O[H])C([H])=C2O1

InChI Identifier

InChI=1S/C25H24O12/c1-10-19(31)22(34-11(2)26)24(35-12(3)27)25(33-10)37-23-20(32)18-16(30)8-15(29)9-17(18)36-21(23)13-4-6-14(28)7-5-13/h4-10,19,22,24-25,28-31H,1-3H3/t10-,19-,22+,24+,25-/m0/s1

InChI Key

BHCRVKVXJRBQJR-YPDHAKIYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Zingiber aromaticum	JEOL database	Usia, T., et al, J. Nat. Prod. 67, 1079 (2004)
Zingiber spectabile	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.26	ALOGPS
logP	2.09	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.05 m³·mol⁻¹	ChemAxon
Polarizability	49.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

9378180

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11203112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Usia, T., et al. (2004). Usia, T., et al, J. Nat. Prod. 67, 1079 (2004). J. Nat. Prod..

Showing NP-Card for kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside) (NP0027403)

MOL for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

3D MOL for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

3D SDF for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

3D-SDF for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

PDB for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

3D PDB for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

SMILES for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

INCHI for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

Structure for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))

3D Structure for NP0027403 (kaempferol-3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside))