NP-MRD: Showing NP-Card for pleioside A (NP0027657)

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Record Information

Version

1.0

Created at

2021-06-19 19:45:14 UTC

Updated at

2021-06-29 23:53:54 UTC

NP-MRD ID

NP0027657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pleioside A

Provided By

JEOL Database JEOL Logo

Description

pleioside A is found in Ananas comosus and Pleioblastus amarus. It was first documented in 2004 (Wang, H.-B., et al.). Based on a literature review very few articles have been published on 2-(3,5-dimethoxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121453D          

 62 65  0  0  0  0            999 V2000
    2.3793   -0.7779    7.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -2.1753    7.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6712   -4.0842    5.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -4.7501    4.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -6.0983    4.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -4.0400    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0604   -4.6998    2.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192121453D          

 62 65  0  0  0  0            999 V2000
    2.3793   -0.7779    7.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -2.1753    7.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7815   -6.0983    4.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -4.0400    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0604   -4.6998    2.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -5.9056    2.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5714    5.6225   -2.4723 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9160    2.2000   -3.2033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8028    1.1057   -2.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    0.4675   -0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073    1.6646   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049    2.0126   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -0.4173    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -1.9088    2.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1018   -1.9964    4.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954   -0.2016    6.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -0.5216    8.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481   -0.5134    7.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -4.6425    6.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -6.4355    3.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032   -4.3405    0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -2.8902   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -2.6557   -3.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523   -3.3786   -2.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -2.8211   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8224    5.7290   -3.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2004    6.5799   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    4.3696   -2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143    4.8535   -4.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0347    3.4633   -1.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7100    2.1580   -4.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602    0.2919   -3.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.2779   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952    2.9750   -0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    2.1363    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.1840    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.9269    4.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 35 34  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 34  1  0  0  0  0
 12 33  2  0  0  0  0
 22 23  1  0  0  0  0
 33 30  1  0  0  0  0
 19 28  1  0  0  0  0
 30 17  2  0  0  0  0
 28 26  1  0  0  0  0
 17 14  1  0  0  0  0
  3  4  2  0  0  0  0
 14 13  2  0  0  0  0
 13 12  1  0  0  0  0
 11 12  1  0  0  0  0
 26 24  1  0  0  0  0
  3  2  1  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  5  7  2  0  0  0  0
  5  6  1  0  0  0  0
 24 21  1  0  0  0  0
  8  9  2  0  0  0  0
 35 36  2  0  0  0  0
 14 15  1  0  0  0  0
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 36  3  1  0  0  0  0
 30 31  1  0  0  0  0
 35  7  1  0  0  0  0
 15 16  1  0  0  0  0
 21 20  1  0  0  0  0
 31 32  1  0  0  0  0
 21 22  1  0  0  0  0
 19 18  1  0  0  0  0
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 24 52  1  6  0  0  0
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 28 56  1  6  0  0  0
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 22 49  1  0  0  0  0
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  4 40  1  0  0  0  0
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 33 61  1  0  0  0  0
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 16 46  1  0  0  0  0
 32 58  1  0  0  0  0
 32 59  1  0  0  0  0
 32 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C(OC([H])([H])[H])=C1[H])C1=C([H])C(OC([H])([H])[H])=C(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O12/c1-31-11-6-12(26)19-13(27)8-14(34-15(19)7-11)10-4-16(32-2)23(17(5-10)33-3)36-24-22(30)21(29)20(28)18(9-25)35-24/h4-8,18,20-22,24-26,28-30H,9H2,1-3H3/t18-,20-,21+,22-,24+/m0/s1

> <INCHI_KEY>
VEXAWZKDFANDTL-RDYNEMLHSA-N

> <FORMULA>
C24H26O12

> <MOLECULAR_WEIGHT>
506.46

> <EXACT_MASS>
506.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.818563958256426

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,5-dimethoxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.2691725649999994

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19983232209042

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.365639917630102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092366207709

> <JCHEM_POLAR_SURFACE_AREA>
173.6

> <JCHEM_REFRACTIVITY>
122.46700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,5-dimethoxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    2.1073    1.6646   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1018   -1.9964    4.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954   -0.2016    6.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4478   -2.8902   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -2.6557   -3.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523   -3.3786   -2.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -2.8211   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278    2.0748   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8224    5.7290   -3.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2964    5.8483   -3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2602    0.2919   -3.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.2779   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952    2.9750   -0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    2.1363    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.1840    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.9269    4.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 24 25  1  0
 26 27  1  0
 28 29  1  0
 35 34  1  0
  7  8  1  0
  8 10  1  0
 10 11  2  0
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 12 33  2  0
 22 23  1  0
 33 30  1  0
 19 28  1  0
 30 17  2  0
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  4  5  1  0
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  5  6  1  0
 24 21  1  0
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 35 36  2  0
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 17 18  1  0
 36  3  1  0
 30 31  1  0
 35  7  1  0
 15 16  1  0
 21 20  1  0
 31 32  1  0
 21 22  1  0
 19 18  1  0
 19 47  1  1
 24 52  1  6
 25 53  1  0
 26 54  1  1
 27 55  1  0
 28 56  1  6
 29 57  1  0
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 36 62  1  0
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 33 61  1  0
 13 43  1  0
  1 37  1  0
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 16 44  1  0
 16 45  1  0
 16 46  1  0
 32 58  1  0
 32 59  1  0
 32 60  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       2.379  -0.778   7.464  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.601  -2.175   7.319  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.449  -2.705   6.068  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.671  -4.084   5.987  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.549  -4.750   4.770  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.781  -6.098   4.773  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.202  -4.040   3.620  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.060  -4.700   2.317  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.240  -5.906   2.190  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.691  -3.853   1.175  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.496  -2.542   1.376  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.131  -1.636   0.269  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.094  -1.961  -0.621  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.251  -1.091  -1.658  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.259  -1.310  -2.565  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.822  -2.617  -2.605  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.438   0.126  -1.786  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.095   0.944  -2.840  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.601   2.121  -2.399  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.198   3.275  -2.677  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.438   4.493  -2.252  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.571   5.622  -2.472  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.785   5.303  -1.782  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.732   4.715  -3.039  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.416   5.886  -2.590  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.646   3.500  -2.864  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.801   3.658  -3.705  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.916   2.200  -3.203  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.803   1.106  -2.917  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.484   0.468  -0.912  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.107   1.665  -1.142  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.205   2.013  -0.308  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.814  -0.417   0.117  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.637  -1.909   2.601  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.980  -2.667   3.694  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.102  -1.996   4.915  0.00  0.00           C+0
HETATM   37  H   UNK     0       3.095  -0.202   6.869  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.538  -0.522   8.516  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.348  -0.513   7.208  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.942  -4.643   6.881  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.662  -6.436   3.856  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.603  -4.340   0.213  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.448  -2.890  -0.475  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.514  -2.656  -3.452  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.052  -3.379  -2.767  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.398  -2.821  -1.696  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.828   2.075  -1.323  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.636   4.425  -1.174  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.822   5.729  -3.533  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.200   6.580  -2.096  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.966   4.370  -2.014  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.514   4.854  -4.105  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.296   5.848  -3.018  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.035   3.463  -1.838  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.249   2.787  -3.684  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.710   2.158  -4.280  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.260   0.292  -3.003  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.013   1.278  -0.390  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.595   2.975  -0.653  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.884   2.136   0.731  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.613  -0.184   0.815  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.921  -0.927   4.936  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   36                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   41                                                       
CONECT    7    8    5   35                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   42                                                  
CONECT   11   10   34   12                                                  
CONECT   12   33   13   11                                                  
CONECT   13   14   12   43                                                  
CONECT   14   17   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   44   45   46                                             
CONECT   17   30   14   18                                                  
CONECT   18   17   19                                                       
CONECT   19   20   28   18   47                                             
CONECT   20   19   21                                                       
CONECT   21   24   20   22   48                                             
CONECT   22   23   21   49   50                                             
CONECT   23   22   51                                                       
CONECT   24   25   26   21   52                                             
CONECT   25   24   53                                                       
CONECT   26   27   28   24   54                                             
CONECT   27   26   55                                                       
CONECT   28   29   19   26   56                                             
CONECT   29   28   57                                                       
CONECT   30   33   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   58   59   60                                             
CONECT   33   12   30   61                                                  
CONECT   34   35   11                                                       
CONECT   35   34   36    7                                                  
CONECT   36   35    3   62                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    4                                                            
CONECT   41    6                                                            
CONECT   42   10                                                            
CONECT   43   13                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   32                                                            
CONECT   59   32                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   36                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    2.3793   -0.7779    7.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -2.1753    7.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -2.7052    6.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -4.0842    5.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -4.7501    4.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -6.0983    4.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -4.0400    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0604   -4.6998    2.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -5.9056    2.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6907   -3.8526    1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958   -2.5415    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309   -1.6360    0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938   -1.9607   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -1.0915   -1.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -1.3101   -2.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -2.6171   -2.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    0.1261   -1.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0946    0.9436   -2.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    2.1207   -2.3992 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1978    3.2751   -2.6769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4378    4.4931   -2.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5714    5.6225   -2.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848    5.3033   -1.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321    4.7154   -3.0387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4163    5.8858   -2.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    3.4998   -2.8641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8015    3.6575   -3.7046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160    2.2000   -3.2033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8028    1.1057   -2.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    0.4675   -0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073    1.6646   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049    2.0126   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -0.4173    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -1.9088    2.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -2.6674    3.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018   -1.9964    4.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954   -0.2016    6.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -0.5216    8.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481   -0.5134    7.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -4.6425    6.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -6.4355    3.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032   -4.3405    0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -2.8902   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -2.6557   -3.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523   -3.3786   -2.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -2.8211   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278    2.0748   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6361    4.4246   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8224    5.7290   -3.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2004    6.5799   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    4.3696   -2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143    4.8535   -4.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2964    5.8483   -3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    3.4633   -1.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2489    2.7866   -3.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100    2.1580   -4.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602    0.2919   -3.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.2779   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952    2.9750   -0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    2.1363    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.1840    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.9269    4.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 24 25  1  0
 26 27  1  0
 28 29  1  0
 35 34  1  0
  7  8  1  0
  8 10  1  0
 10 11  2  0
 11 34  1  0
 12 33  2  0
 22 23  1  0
 33 30  1  0
 19 28  1  0
 30 17  2  0
 28 26  1  0
 17 14  1  0
  3  4  2  0
 14 13  2  0
 13 12  1  0
 11 12  1  0
 26 24  1  0
  3  2  1  0
  4  5  1  0
  2  1  1  0
  5  7  2  0
  5  6  1  0
 24 21  1  0
  8  9  2  0
 35 36  2  0
 14 15  1  0
 17 18  1  0
 36  3  1  0
 30 31  1  0
 35  7  1  0
 15 16  1  0
 21 20  1  0
 31 32  1  0
 21 22  1  0
 19 18  1  0
 19 47  1  1
 24 52  1  6
 25 53  1  0
 26 54  1  1
 27 55  1  0
 28 56  1  6
 29 57  1  0
 22 49  1  0
 22 50  1  0
 21 48  1  1
 23 51  1  0
  4 40  1  0
 36 62  1  0
 10 42  1  0
 33 61  1  0
 13 43  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  6 41  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₁₂

Average Mass

506.4600 Da

Monoisotopic Mass

506.14243 Da

IUPAC Name

2-(3,5-dimethoxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

2-(3,5-dimethoxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxychromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C(OC([H])([H])[H])=C1[H])C1=C([H])C(OC([H])([H])[H])=C(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C24H26O12/c1-31-11-6-12(26)19-13(27)8-14(34-15(19)7-11)10-4-16(32-2)23(17(5-10)33-3)36-24-22(30)21(29)20(28)18(9-25)35-24/h4-8,18,20-22,24-26,28-30H,9H2,1-3H3/t18-,20-,21+,22-,24+/m0/s1

InChI Key

VEXAWZKDFANDTL-RDYNEMLHSA-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
Ananas comosus	Plant	KNApSAcK
Pleioblastus amarus	JEOL database	Wang, H.-B., et al, Phytochemistry 65, 969 (2004)

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
Flavonoid-4p-o-glycoside
3p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Chromone
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
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	0.84	ALOGPS
logP	0.27	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	173.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.47 m³·mol⁻¹	ChemAxon
Polarizability	50.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

8611647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10436223

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, H.-B., et al. (2004). Wang, H.-B., et al, Phytochemistry 65, 969 (2004). Phytochem..

Showing NP-Card for pleioside A (NP0027657)

MOL for NP0027657 (pleioside A)

3D MOL for NP0027657 (pleioside A)

3D SDF for NP0027657 (pleioside A)

3D-SDF for NP0027657 (pleioside A)

PDB for NP0027657 (pleioside A)

3D PDB for NP0027657 (pleioside A)

SMILES for NP0027657 (pleioside A)

INCHI for NP0027657 (pleioside A)

Structure for NP0027657 (pleioside A)

3D Structure for NP0027657 (pleioside A)