NP-MRD: Showing NP-Card for bauhiniaside A (NP0038293)

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Record Information

Version

2.0

Created at

2021-06-20 21:01:07 UTC

Updated at

2021-06-30 00:11:00 UTC

NP-MRD ID

NP0038293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bauhiniaside A

Provided By

JEOL Database JEOL Logo

Description

1-(4-Hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-methoxyphenyl)propan-1-one 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. bauhiniaside A is found in Bauhinia glauca subsp. pernervosa and Bauhinia glauca. bauhiniaside A was first documented in 2009 (Wu, Z.-B., et al.). Based on a literature review very few articles have been published on 1-(4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-methoxyphenyl)propan-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123013D          

 57 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123013D          

 57 59  0  0  0  0            999 V2000
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    1.9593    4.2929   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    4.3939   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    6.1180   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590    5.6086   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103    3.4132    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696    1.8460    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9155    1.3203    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070    1.9643    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131   -0.2590   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143    0.4351   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -2.1033   -1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -3.8453   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -4.9246   -2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -3.4986   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2485   -3.4596    1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599   -4.5141    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8162   -2.7901    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8381   -4.4654    2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5905   -3.5406   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4707   -1.9727    3.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4087   -3.4056    5.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -3.6121    4.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -1.6958    5.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0779   -0.8075    3.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -1.2896    2.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307    3.3987   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    4.9811   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 31  2  0  0  0  0
 21 20  1  0  0  0  0
 31 30  1  0  0  0  0
 20 19  1  0  0  0  0
 30  6  2  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
 24 25  1  0  0  0  0
  7  8  1  0  0  0  0
 26 27  1  0  0  0  0
  8  9  1  0  0  0  0
 28 29  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 22 23  1  0  0  0  0
 14 16  1  0  0  0  0
 19 28  1  0  0  0  0
 16 17  2  0  0  0  0
 17 11  1  0  0  0  0
 28 26  1  0  0  0  0
 11 12  2  0  0  0  0
  5  4  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 17 18  1  0  0  0  0
 26 24  1  0  0  0  0
 14 15  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 24 21  1  0  0  0  0
  2  1  1  0  0  0  0
 21 22  1  0  0  0  0
 19 18  1  0  0  0  0
 29 55  1  0  0  0  0
 19 45  1  1  0  0  0
 24 50  1  6  0  0  0
 25 51  1  0  0  0  0
 26 52  1  1  0  0  0
 27 53  1  0  0  0  0
 28 54  1  6  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 21 46  1  1  0  0  0
 23 49  1  0  0  0  0
  5 36  1  0  0  0  0
  4 35  1  0  0  0  0
 31 57  1  0  0  0  0
 30 56  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
 16 44  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  0  0  0  0
 15 43  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038293

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O9/c1-29-14-6-2-12(3-7-14)4-9-16(25)15-8-5-13(24)10-17(15)30-22-21(28)20(27)19(26)18(11-23)31-22/h2-3,5-8,10,18-24,26-28H,4,9,11H2,1H3/t18-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
ADVQDJMRDIRSLK-QMCAAQAGSA-N

> <FORMULA>
C22H26O9

> <MOLECULAR_WEIGHT>
434.441

> <EXACT_MASS>
434.157682417

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.51665990245172

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-methoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.776931817

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200120097596923

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.775593809003394

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346267868

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
108.35310000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.49e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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   -5.1335   -2.6772    1.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -3.5357    2.2516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2615   -3.7338    1.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1510   -4.2017    0.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9160   -2.9193    3.6520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5852   -3.7848    4.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4949   -2.6605    4.1500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5592   -1.9819    5.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -1.8340    3.1452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3490   -1.7535    3.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    3.3953   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    4.2929   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    4.3939   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    6.1180   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2696    1.8460    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9155    1.3203    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070    1.9643    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131   -0.2590   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143    0.4351   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -2.1033   -1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -3.8453   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -4.9246   -2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -3.4986   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2485   -3.4596    1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599   -4.5141    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8162   -2.7901    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8381   -4.4654    2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5905   -3.5406   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4707   -1.9727    3.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4087   -3.4056    5.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -3.6121    4.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -1.6958    5.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0779   -0.8075    3.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -1.2896    2.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307    3.3987   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    4.9811   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 31  2  0
 21 20  1  0
 31 30  1  0
 20 19  1  0
 30  6  2  0
  6  5  1  0
  6  7  1  0
 24 25  1  0
  7  8  1  0
 26 27  1  0
  8  9  1  0
 28 29  1  0
  9 10  2  0
  9 11  1  0
 22 23  1  0
 14 16  1  0
 19 28  1  0
 16 17  2  0
 17 11  1  0
 28 26  1  0
 11 12  2  0
  5  4  2  0
 12 13  1  0
 13 14  2  0
 17 18  1  0
 26 24  1  0
 14 15  1  0
  4  3  1  0
  3  2  1  0
 24 21  1  0
  2  1  1  0
 21 22  1  0
 19 18  1  0
 29 55  1  0
 19 45  1  1
 24 50  1  6
 25 51  1  0
 26 52  1  1
 27 53  1  0
 28 54  1  6
 22 47  1  0
 22 48  1  0
 21 46  1  1
 23 49  1  0
  5 36  1  0
  4 35  1  0
 31 57  1  0
 30 56  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 16 44  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.436   5.329  -1.448  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.061   5.244  -1.799  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.309   4.318  -1.129  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.771   3.431  -0.157  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.889   2.530   0.450  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.535   2.507   0.096  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.592   1.518   0.735  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.527   0.218  -0.064  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.454  -0.757   0.557  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.747  -0.731   1.752  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.048  -1.802  -0.323  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.274  -2.391  -1.333  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.825  -3.383  -2.145  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.144  -3.779  -1.954  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.639  -4.742  -2.783  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.927  -3.206  -0.958  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.372  -2.227  -0.125  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.134  -1.596   0.823  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.770  -2.491   1.751  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.133  -2.677   1.351  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.858  -3.536   2.252  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.261  -3.734   1.669  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.151  -4.202   0.321  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.916  -2.919   3.652  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.585  -3.785   4.569  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.495  -2.660   4.150  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.559  -1.982   5.415  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.693  -1.834   3.145  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.349  -1.754   3.645  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.076   3.395  -0.883  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.959   4.293  -1.487  0.00  0.00           C+0
HETATM   32  H   UNK     0       5.959   4.394  -1.673  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.888   6.118  -2.056  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.559   5.609  -0.396  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.810   3.413   0.153  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.270   1.846   1.206  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.916   1.320   1.766  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.407   1.964   0.821  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.513  -0.259  -0.095  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.214   0.435  -1.093  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.762  -2.103  -1.493  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.229  -3.845  -2.928  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.564  -4.925  -2.547  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.965  -3.499  -0.839  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.248  -3.460   1.778  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.360  -4.514   2.269  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.816  -2.790   1.640  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.838  -4.465   2.243  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.590  -3.541  -0.127  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.471  -1.973   3.633  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.409  -3.406   5.455  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.988  -3.612   4.355  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.639  -1.696   5.592  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.078  -0.808   3.110  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.810  -1.290   2.959  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.031   3.399  -1.181  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.592   4.981  -2.245  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3   31    4    2                                                  
CONECT    4    5    3   35                                                  
CONECT    5    6    4   36                                                  
CONECT    6   30    5    7                                                  
CONECT    7    6    8   37   38                                             
CONECT    8    7    9   39   40                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   17   12                                                  
CONECT   12   11   13   41                                                  
CONECT   13   12   14   42                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   43                                                       
CONECT   16   14   17   44                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   20   28   18   45                                             
CONECT   20   21   19                                                       
CONECT   21   20   24   22   46                                             
CONECT   22   23   21   47   48                                             
CONECT   23   22   49                                                       
CONECT   24   25   26   21   50                                             
CONECT   25   24   51                                                       
CONECT   26   27   28   24   52                                             
CONECT   27   26   53                                                       
CONECT   28   29   19   26   54                                             
CONECT   29   28   55                                                       
CONECT   30   31    6   56                                                  
CONECT   31    3   30   57                                                  
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
CONECT   57   31                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
    5.4360    5.3291   -1.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0608    5.2438   -1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088    4.3180   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    3.4313   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    2.5300    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    2.5070    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924    1.5180    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    0.2179   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541   -0.7574    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -0.7312    1.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482   -1.8018   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2738   -2.3906   -1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -3.3830   -2.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1440   -3.7792   -1.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -4.7417   -2.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271   -3.2058   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -2.2266   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -1.5961    0.8233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7697   -2.4913    1.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1335   -2.6772    1.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584   -3.5357    2.2516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2615   -3.7338    1.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1510   -4.2017    0.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9160   -2.9193    3.6520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5852   -3.7848    4.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4949   -2.6605    4.1500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5592   -1.9819    5.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -1.8340    3.1452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3490   -1.7535    3.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    3.3953   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    4.2929   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    4.3939   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    6.1180   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590    5.6086   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103    3.4132    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696    1.8460    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9155    1.3203    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070    1.9643    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131   -0.2590   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143    0.4351   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -2.1033   -1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -3.8453   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -4.9246   -2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -3.4986   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2485   -3.4596    1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599   -4.5141    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8162   -2.7901    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8381   -4.4654    2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5905   -3.5406   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4707   -1.9727    3.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4087   -3.4056    5.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -3.6121    4.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -1.6958    5.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0779   -0.8075    3.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -1.2896    2.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307    3.3987   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    4.9811   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 31  2  0
 21 20  1  0
 31 30  1  0
 20 19  1  0
 30  6  2  0
  6  5  1  0
  6  7  1  0
 24 25  1  0
  7  8  1  0
 26 27  1  0
  8  9  1  0
 28 29  1  0
  9 10  2  0
  9 11  1  0
 22 23  1  0
 14 16  1  0
 19 28  1  0
 16 17  2  0
 17 11  1  0
 28 26  1  0
 11 12  2  0
  5  4  2  0
 12 13  1  0
 13 14  2  0
 17 18  1  0
 26 24  1  0
 14 15  1  0
  4  3  1  0
  3  2  1  0
 24 21  1  0
  2  1  1  0
 21 22  1  0
 19 18  1  0
 29 55  1  0
 19 45  1  1
 24 50  1  6
 25 51  1  0
 26 52  1  1
 27 53  1  0
 28 54  1  6
 22 47  1  0
 22 48  1  0
 21 46  1  1
 23 49  1  0
  5 36  1  0
  4 35  1  0
 31 57  1  0
 30 56  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 16 44  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₉

Average Mass

434.4410 Da

Monoisotopic Mass

434.15768 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H26O9/c1-29-14-6-2-12(3-7-14)4-9-16(25)15-8-5-13(24)10-17(15)30-22-21(28)20(27)19(26)18(11-23)31-22/h2-3,5-8,10,18-24,26-28H,4,9,11H2,1H3/t18-,19-,20+,21-,22-/m1/s1

InChI Key

ADVQDJMRDIRSLK-QMCAAQAGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Bauhinia glauca subsp. pernervosa	JEOL database	Wu, Z.-B., et al, Chem. Pharm. Bull. 57, 628 (2009)
Cheniella glauca	LOTUS Database	35616633

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
Phenolic glycoside
Linear 1,3-diarylpropanoid
Cinnamylphenol
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Butyrophenone
Phenylketone
Phenoxy compound
Phenol ether
Anisole
Benzoyl
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Alcohol
Hydrocarbon derivative
Aldehyde
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.92	ALOGPS
logP	0.78	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.35 m³·mol⁻¹	ChemAxon
Polarizability	45.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10306384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21722185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu, Z.-B., et al. (2009). Wu, Z.-B., et al, Chem. Pharm. Bull. 57, 628 (2009). Chem. Pharm. Bull..

Showing NP-Card for bauhiniaside A (NP0038293)

MOL for NP0038293 (bauhiniaside A)

3D MOL for NP0038293 (bauhiniaside A)

3D SDF for NP0038293 (bauhiniaside A)

3D-SDF for NP0038293 (bauhiniaside A)

PDB for NP0038293 (bauhiniaside A)

3D PDB for NP0038293 (bauhiniaside A)

SMILES for NP0038293 (bauhiniaside A)

INCHI for NP0038293 (bauhiniaside A)

Structure for NP0038293 (bauhiniaside A)

3D Structure for NP0038293 (bauhiniaside A)