NP-MRD: Showing NP-Card for (-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone (NP0042724)

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Record Information

Version

2.0

Created at

2021-06-21 00:18:50 UTC

Updated at

2021-06-30 00:17:58 UTC

NP-MRD ID

NP0042724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone

Provided By

JEOL Database JEOL Logo

Description

(2S)-8-Hydroxy-2alpha-(3-hydroxy-4-methoxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-4H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. (-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone is found in Bidens gardneri Bak. (Asteraceae). (-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone was first documented in 2013 (Silva, D. B., et al.). Based on a literature review very few articles have been published on (2S)-8-Hydroxy-2alpha-(3-hydroxy-4-methoxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-4H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102183D          

 57 60  0  0  0  0            999 V2000
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   -2.2221   -6.8854    2.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8600   -4.7040    1.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5761   -3.3339    1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906   -2.7737    2.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867   -1.2902    2.3188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -0.4893    3.1488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8199    0.9652    3.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.7686    3.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2543    1.4049    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    2.7611    1.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 32  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102183D          

 57 60  0  0  0  0            999 V2000
   -3.3097   -7.4920    2.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -6.8854    2.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2253   -0.8958    0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -3.6140    3.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -4.9720    3.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849   -5.7583    4.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -7.0821    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -7.3922    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -8.5598    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085   -5.0834    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -2.7031    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.1234    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344   -0.7899    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.6046    2.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3525    4.2133    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8372   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    3.1195   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    5.9192   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    5.5756   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315    4.6955   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653    4.0355   -4.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    2.8168   -4.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.2093   -3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    0.7579   -5.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668    2.4888   -4.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466    0.4782   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -0.9322   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -3.2266    3.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -6.6587    3.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 32  2  0  0  0  0
 18 17  1  0  0  0  0
 32 31  1  0  0  0  0
 31  6  2  0  0  0  0
 17 16  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  2  0  0  0  0
 29 27  2  0  0  0  0
 29 11  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 29 30  1  0  0  0  0
 11  9  1  0  0  0  0
  9  8  1  0  0  0  0
  7 30  1  0  0  0  0
  8  7  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  2  0  0  0  0
 16 25  1  0  0  0  0
 14 27  1  0  0  0  0
  6  5  1  0  0  0  0
 25 23  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  1  0  0  0  0
  5  4  2  0  0  0  0
  3  2  1  0  0  0  0
 23 21  1  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
 27 28  1  0  0  0  0
 21 18  1  0  0  0  0
 32 33  1  0  0  0  0
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 16 15  1  0  0  0  0
 24 52  1  0  0  0  0
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 16 44  1  1  0  0  0
 21 49  1  6  0  0  0
 22 50  1  0  0  0  0
 23 51  1  1  0  0  0
 25 53  1  6  0  0  0
 26 54  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 18 45  1  1  0  0  0
  5 38  1  0  0  0  0
  4 37  1  0  0  0  0
 31 56  1  0  0  0  0
  8 40  1  0  0  0  0
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 12 42  1  0  0  0  0
  7 39  1  1  0  0  0
 13 43  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
 28 55  1  0  0  0  0
 33 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C(=C1[H])[C@@]1([H])OC2=C(O[H])C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])=C([H])C([H])=C2C(=O)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O11/c1-30-13-4-2-9(6-12(13)25)15-7-11(24)10-3-5-14(18(27)21(10)31-15)32-22-20(29)19(28)17(26)16(8-23)33-22/h2-6,15-17,19-20,22-23,25-29H,7-8H2,1H3/t15-,16+,17+,19-,20+,22+/m0/s1

> <INCHI_KEY>
MVIJSQNWYLPBGP-PFYPPANJSA-N

> <FORMULA>
C22H24O11

> <MOLECULAR_WEIGHT>
464.423

> <EXACT_MASS>
464.131861593

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.49613407872141

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-8-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.24063130866666602

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.822997351854848

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.631259125593425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354942014

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
109.8974

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-8-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
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    4.1006    5.2088   -1.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238    5.2292   -1.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3058    3.3144   -3.8070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.9466   -3.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5526    1.5580   -5.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160    1.9183   -3.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3749    0.5550   -3.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.8557   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227   -0.0692   -1.4738 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2253   -0.8958    0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -3.6140    3.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -4.9720    3.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7085   -5.0834    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -2.7031    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.1234    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344   -0.7899    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.6046    2.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096    3.5074    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525    4.2133    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8372   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    3.1195   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    5.9192   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    5.5756   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315    4.6955   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653    4.0355   -4.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    2.8168   -4.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.2093   -3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    0.7579   -5.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668    2.4888   -4.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466    0.4782   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -0.9322   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -3.2266    3.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -6.6587    3.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 32  2  0
 18 17  1  0
 32 31  1  0
 31  6  2  0
 17 16  1  0
 13 12  1  0
 12 11  2  0
 29 27  2  0
 29 11  1  0
 21 22  1  0
 23 24  1  0
 25 26  1  0
 29 30  1  0
 11  9  1  0
  9  8  1  0
  7 30  1  0
  8  7  1  0
 19 20  1  0
  9 10  2  0
 13 14  2  0
 16 25  1  0
 14 27  1  0
  6  5  1  0
 25 23  1  0
 14 15  1  0
  7  6  1  0
  5  4  2  0
  3  2  1  0
 23 21  1  0
  2  1  1  0
  4  3  1  0
 27 28  1  0
 21 18  1  0
 32 33  1  0
 18 19  1  0
 16 15  1  0
 24 52  1  0
 20 48  1  0
 16 44  1  1
 21 49  1  6
 22 50  1  0
 23 51  1  1
 25 53  1  6
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 19 46  1  0
 19 47  1  0
 18 45  1  1
  5 38  1  0
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 31 56  1  0
  8 40  1  0
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  7 39  1  1
 13 43  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 28 55  1  0
 33 57  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.310  -7.492   2.044  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.222  -6.885   2.733  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.063  -5.535   2.559  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.860  -4.704   1.776  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.576  -3.334   1.693  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.491  -2.774   2.389  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.187  -1.290   2.319  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.181  -0.489   3.149  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.820   0.965   3.039  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.030   1.769   3.941  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.254   1.405   1.748  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.010   2.761   1.499  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.531   3.161   0.249  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.291   2.204  -0.736  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.125   2.618  -1.970  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.553   2.503  -2.106  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.132   3.807  -1.974  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.552   3.801  -2.163  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.101   5.209  -1.891  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.524   5.229  -1.862  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.890   3.342  -3.589  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.306   3.314  -3.807  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.312   1.947  -3.817  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.553   1.558  -5.179  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.816   1.918  -3.510  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.375   0.555  -3.632  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.545   0.856  -0.487  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.323  -0.069  -1.474  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.009   0.448   0.763  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.225  -0.896   0.935  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.696  -3.614   3.179  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.988  -4.972   3.253  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.185  -5.758   4.035  0.00  0.00           O+0
HETATM   34  H   UNK     0      -4.268  -7.082   2.381  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.195  -7.392   0.960  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.302  -8.560   2.283  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.708  -5.083   1.216  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.213  -2.703   1.075  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.161  -1.123   2.679  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.134  -0.790   4.201  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.211  -0.605   2.791  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.210   3.507   2.266  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.353   4.213   0.041  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.979   1.837  -1.341  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.015   3.119  -1.436  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.752   5.919  -2.649  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.737   5.576  -0.925  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.832   4.696  -2.626  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.465   4.035  -4.326  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.420   2.817  -4.645  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.845   1.209  -3.203  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.003   0.758  -5.314  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.267   2.489  -4.269  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.547   0.478  -3.108  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.587  -0.932  -1.094  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.150  -3.227   3.742  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.556  -6.659   3.951  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3   32    2    4                                                  
CONECT    4    5    3   37                                                  
CONECT    5    6    4   38                                                  
CONECT    6   31    5    7                                                  
CONECT    7   30    8    6   39                                             
CONECT    8    9    7   40   41                                             
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12   29    9                                                  
CONECT   12   13   11   42                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13   27   15                                                  
CONECT   15   14   16                                                       
CONECT   16   17   25   15   44                                             
CONECT   17   18   16                                                       
CONECT   18   17   21   19   45                                             
CONECT   19   20   18   46   47                                             
CONECT   20   19   48                                                       
CONECT   21   22   23   18   49                                             
CONECT   22   21   50                                                       
CONECT   23   24   25   21   51                                             
CONECT   24   23   52                                                       
CONECT   25   26   16   23   53                                             
CONECT   26   25   54                                                       
CONECT   27   29   14   28                                                  
CONECT   28   27   55                                                       
CONECT   29   27   11   30                                                  
CONECT   30   29    7                                                       
CONECT   31   32    6   56                                                  
CONECT   32    3   31   33                                                  
CONECT   33   32   57                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   16                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   28                                                            
CONECT   56   31                                                            
CONECT   57   33                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
   -3.3097   -7.4920    2.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -6.8854    2.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -5.5351    2.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -4.7040    1.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5761   -3.3339    1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906   -2.7737    2.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867   -1.2902    2.3188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -0.4893    3.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199    0.9652    3.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.7686    3.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2543    1.4049    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    2.7611    1.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    3.1608    0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    2.2041   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251    2.6177   -1.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1324    3.8073   -1.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519    3.8013   -2.1626 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1006    5.2088   -1.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238    5.2292   -1.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    3.3418   -3.5892 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3058    3.3144   -3.8070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    1.9466   -3.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5526    1.5580   -5.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160    1.9183   -3.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3749    0.5550   -3.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.8557   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3227   -0.0692   -1.4738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094    0.4477    0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253   -0.8958    0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -3.6140    3.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -4.9720    3.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849   -5.7583    4.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -7.0821    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -7.3922    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -8.5598    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085   -5.0834    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -2.7031    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.1234    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344   -0.7899    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.6046    2.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096    3.5074    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525    4.2133    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788    1.8372   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    3.1195   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    5.9192   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    5.5756   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315    4.6955   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653    4.0355   -4.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    2.8168   -4.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.2093   -3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    0.7579   -5.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668    2.4888   -4.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466    0.4782   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -0.9322   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -3.2266    3.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -6.6587    3.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 32  2  0
 18 17  1  0
 32 31  1  0
 31  6  2  0
 17 16  1  0
 13 12  1  0
 12 11  2  0
 29 27  2  0
 29 11  1  0
 21 22  1  0
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 25 26  1  0
 29 30  1  0
 11  9  1  0
  9  8  1  0
  7 30  1  0
  8  7  1  0
 19 20  1  0
  9 10  2  0
 13 14  2  0
 16 25  1  0
 14 27  1  0
  6  5  1  0
 25 23  1  0
 14 15  1  0
  7  6  1  0
  5  4  2  0
  3  2  1  0
 23 21  1  0
  2  1  1  0
  4  3  1  0
 27 28  1  0
 21 18  1  0
 32 33  1  0
 18 19  1  0
 16 15  1  0
 24 52  1  0
 20 48  1  0
 16 44  1  1
 21 49  1  6
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 25 53  1  6
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 19 46  1  0
 19 47  1  0
 18 45  1  1
  5 38  1  0
  4 37  1  0
 31 56  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  0
  7 39  1  1
 13 43  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 28 55  1  0
 33 57  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-8-Hydroxy-2a-(3-hydroxy-4-methoxyphenyl)-7-(b-D-glucopyranosyloxy)-2,3-dihydro-4H-1-benzopyran-4-one	Generator
(2S)-8-Hydroxy-2α-(3-hydroxy-4-methoxyphenyl)-7-(β-D-glucopyranosyloxy)-2,3-dihydro-4H-1-benzopyran-4-one	Generator

Chemical Formula

C₂₂H₂₄O₁₁

Average Mass

464.4230 Da

Monoisotopic Mass

464.13186 Da

IUPAC Name

(2S)-8-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-8-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C(=C1[H])[C@@]1([H])OC2=C(O[H])C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])=C([H])C([H])=C2C(=O)C1([H])[H]

InChI Identifier

InChI=1S/C22H24O11/c1-30-13-4-2-9(6-12(13)25)15-7-11(24)10-3-5-14(18(27)21(10)31-15)32-22-20(29)19(28)17(26)16(8-23)33-22/h2-6,15-17,19-20,22-23,25-29H,7-8H2,1H3/t15-,16+,17+,19-,20+,22+/m0/s1

InChI Key

MVIJSQNWYLPBGP-PFYPPANJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Bidens gardneri Bak. (Asteraceae)	JEOL database	Silva, D. B., et. al, Phytochem. 96, 418 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
8-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxane
Monocyclic benzene moiety
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
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	0.16	ALOGPS
logP	-0.24	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.9 m³·mol⁻¹	ChemAxon
Polarizability	46.5 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102497695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Silva, D. B., et al. (2013). Silva, D. B., et. al, Phytochem. 96, 418 (2013). Phytochem..

Showing NP-Card for (-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone (NP0042724)

MOL for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

3D MOL for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

3D SDF for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

3D-SDF for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

PDB for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

3D PDB for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

SMILES for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

INCHI for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

Structure for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)

3D Structure for NP0042724 ((-)-4'-methoxy-7-O-beta-D-glucopyranosyl-8,3'-dihydroxyflavanone)