NP-MRD: Showing NP-Card for Proanthocyanidin A-6 (NP0025690)

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Record Information

Version

1.0

Created at

2021-06-19 17:45:00 UTC

Updated at

2021-06-29 23:50:47 UTC

NP-MRD ID

NP0025690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Proanthocyanidin A-6

Provided By

JEOL Database JEOL Logo

Description

Proanthocyanidin A-6 belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Proanthocyanidin A-6 is found in Aesculus hippocastanum , Parameria laevigata MOLDENKE and Parameria laevigata MOLDENKE . It was first documented in 2014 (PMID: 25356846). Proanthocyanidin A-6 is a moderately basic compound (based on its pKa) (PMID: 30043588) (PMID: 29716563) (PMID: 26051626) (PMID: 25911741).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119453D          

 66 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119453D          

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M  END
> <DATABASE_ID>
NP0025690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]3(OC4=C([H])C5=C(C(O[H])=C4[C@]2([H])[C@@]3([H])O[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O5)C2=C([H])C(O[H])=C(O[H])C([H])=C2[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2/t20-,26-,28-,29-,30+/m1/s1

> <INCHI_KEY>
BEPYKTSNKZMROV-FEEPWOQDSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.51

> <EXACT_MASS>
576.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.918942161075286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,7R,13S,21R)-7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.590532096666666

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111216654632903

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.666792986478557

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8766022958579898

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
144.19630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,7R,13S,21R)-7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 40 65  1  0
 38 64  1  0
 21 52  1  0
  3 44  1  0
  8 46  1  0
 27 54  1  6
 28 55  1  6
 29 56  1  0
 12 47  1  0
 13 48  1  0
 18 51  1  0
  1 43  1  0
  5 45  1  0
 15 49  1  0
 17 50  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  6
 32 60  1  0
 25 53  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  O   UNK     0       6.126   0.785   3.831  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.121   0.024   3.309  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.261  -0.416   1.998  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.254  -1.194   1.432  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.364  -1.625   0.137  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.114  -1.543   2.165  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.991  -1.079   3.480  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.995  -0.301   4.057  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.930  -1.380   4.286  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.800  -2.069   3.688  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.011  -2.622   4.890  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.405  -1.720   5.899  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.128  -2.150   7.015  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.446  -3.490   7.133  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.149  -3.918   8.222  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.055  -4.399   6.156  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.402  -5.711   6.337  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.337  -3.979   5.038  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.122  -1.137   3.073  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.020  -0.910   1.729  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.990  -0.073   1.181  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.971   0.219  -0.181  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.002  -0.338  -1.016  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.992  -1.149  -0.445  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.975  -1.617  -1.275  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.977  -1.468   0.920  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.997  -2.369   1.570  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.287  -3.147   2.684  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.164  -4.145   3.242  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.005  -0.047  -2.497  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.288   0.641  -2.941  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.310  -0.357  -3.109  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.674   1.694  -1.882  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.852   2.605  -2.202  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.087   3.709  -1.353  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.143   4.594  -1.588  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.974   4.376  -2.673  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.008   5.237  -2.907  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.769   3.290  -3.517  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.634   3.127  -4.564  0.00  0.00           O+0
HETATM   41  C   UNK     0      -3.716   2.406  -3.292  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.972   1.039  -0.633  0.00  0.00           O+0
HETATM   43  H   UNK     0       5.888   1.043   4.737  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.149  -0.137   1.440  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.249  -1.374  -0.189  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.882   0.039   5.082  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.164  -0.661   5.811  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.439  -1.444   7.778  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.256  -4.879   8.080  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.042  -6.226   5.594  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.051  -4.714   4.293  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.761   0.356   1.816  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.798  -1.734  -0.756  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.401  -3.105   0.865  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.433  -3.688   2.254  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.793  -3.689   3.833  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.857   0.611  -2.709  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.133  -0.981  -3.056  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.131   1.103  -3.922  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.582  -0.629  -2.211  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.812   2.361  -1.729  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.443   3.880  -0.492  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.314   5.439  -0.929  0.00  0.00           H+0
HETATM   64  H   UNK     0      -6.447   4.877  -3.703  0.00  0.00           H+0
HETATM   65  H   UNK     0      -5.398   2.300  -5.021  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.578   1.564  -3.963  0.00  0.00           H+0
CONECT    1    2   43                                                       
CONECT    2    3    1    8                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   45                                                       
CONECT    6   27    4    7                                                  
CONECT    7    9    8    6                                                  
CONECT    8    7    2   46                                                  
CONECT    9    7   10                                                       
CONECT   10   28    9   19   11                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   47                                                  
CONECT   13   12   14   48                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   49                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   50                                                       
CONECT   18   16   11   51                                                  
CONECT   19   10   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   22   20   52                                                  
CONECT   22   21   23   42                                                  
CONECT   23   24   22   30                                                  
CONECT   24   23   26   25                                                  
CONECT   25   24   53                                                       
CONECT   26   27   20   24                                                  
CONECT   27    6   28   26   54                                             
CONECT   28   27   10   29   55                                             
CONECT   29   28   56                                                       
CONECT   30   23   31   57   58                                             
CONECT   31   30   33   32   59                                             
CONECT   32   31   60                                                       
CONECT   33   34   31   42   61                                             
CONECT   34   35   41   33                                                  
CONECT   35   36   34   62                                                  
CONECT   36   35   37   63                                                  
CONECT   37   39   38   36                                                  
CONECT   38   37   64                                                       
CONECT   39   37   40   41                                                  
CONECT   40   39   65                                                       
CONECT   41   34   39   66                                                  
CONECT   42   22   33                                                       
CONECT   43    1                                                            
CONECT   44    3                                                            
CONECT   45    5                                                            
CONECT   46    8                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   15                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   21                                                            
CONECT   53   25                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   30                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   35                                                            
CONECT   63   36                                                            
CONECT   64   38                                                            
CONECT   65   40                                                            
CONECT   66   41                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  144    0
END

RDKit          3D

66 72  0  0  0  0  0  0  0  0999 V2000
    6.1260    0.7845    3.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2541   -1.1940    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4050   -1.7200    5.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9895   -0.0725    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.2193   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -0.3376   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921   -1.1495   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9972   -2.3692    1.5704 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2870   -3.1472    2.6839 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1644   -4.1452    3.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -0.0465   -2.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6344    3.1265   -4.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9718    1.0391   -0.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    1.0427    4.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1487   -0.1366    1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488   -1.3742   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0506   -4.7139    4.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7608    0.3555    1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7976   -1.7336   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4011   -3.1053    0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331   -3.6885    2.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -3.6894    3.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570    0.6112   -2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1330   -0.9811   -3.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310    1.1031   -3.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5824   -0.6289   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4466    4.8765   -3.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3984    2.3004   -5.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    1.5638   -3.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
  6 27  1  0
 27 28  1  0
 28 10  1  0
 10  9  1  0
 22 21  1  0
 10 19  1  0
 27 26  1  0
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  2  3  2  0
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 33 34  1  0
 14 16  1  0
  3  4  1  0
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  4  6  2  0
  2  1  1  0
 39 37  2  0
  4  5  1  0
  7  8  2  0
 14 15  1  0
  8  2  1  0
 16 17  1  0
 22 23  2  0
  7  6  1  0
 39 40  1  0
 37 38  1  0
 37 36  1  0
 22 42  1  0
 23 30  1  0
 30 31  1  0
 31 33  1  0
 33 42  1  0
 26 24  2  0
 31 32  1  0
 41 39  1  0
 24 25  1  0
 41 66  1  0
 36 63  1  0
 35 62  1  0
 33 61  1  1
 40 65  1  0
 38 64  1  0
 21 52  1  0
  3 44  1  0
  8 46  1  0
 27 54  1  6
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 29 56  1  0
 12 47  1  0
 13 48  1  0
 18 51  1  0
  1 43  1  0
  5 45  1  0
 15 49  1  0
 17 50  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  6
 32 60  1  0
 25 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5100 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

(1R,6R,7R,13S,21R)-7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol

Traditional Name

(1R,6R,7R,13S,21R)-7,13-bis(3,4-dihydroxyphenyl)-8,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-2,4(9),10,15,17,19-hexaene-3,6,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]3(OC4=C([H])C5=C(C(O[H])=C4[C@]2([H])[C@@]3([H])O[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O5)C2=C([H])C(O[H])=C(O[H])C([H])=C2[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C1[H]

InChI Identifier

InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2/t20-,26-,28-,29-,30+/m1/s1

InChI Key

BEPYKTSNKZMROV-FEEPWOQDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum	Plant	KNApSAcK
Parameria laevigata	JEOL database	Kamiya, K., et al, Chem. Pharm. Bull. 49, 551 (2001)
Parameria laevigata MOLDENKE	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

A-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Pyranochromene
Chromane
1-benzopyran
Benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
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	2.46	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	57.92 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

22913199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45359583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Autieri G, Mussano F, Petruzzi M, Carossa M, Genova T, Corsalini M, Carossa S: Proanthocyanidin may improve the shear bond strength at the composites/dentine interface. J Biol Regul Homeost Agents. 2018 Jul-Aug;32(4):1021-1025. [PubMed:30043588 ]
Asma B, Vicky L, Stephanie D, Yves D, Amy H, Sylvie D: Standardised high dose versus low dose cranberry Proanthocyanidin extracts for the prevention of recurrent urinary tract infection in healthy women [PACCANN]: a double blind randomised controlled trial protocol. BMC Urol. 2018 May 2;18(1):29. doi: 10.1186/s12894-018-0342-7. [PubMed:29716563 ]
Ribas-Latre A, Baselga-Escudero L, Casanova E, Arola-Arnal A, Salvado MJ, Blade C, Arola L: Dietary proanthocyanidins modulate BMAL1 acetylation, Nampt expression and NAD levels in rat liver. Sci Rep. 2015 Jun 8;5:10954. doi: 10.1038/srep10954. [PubMed:26051626 ]
Zhu Z, Wang H, Wang Y, Guan S, Wang F, Tang J, Zhang R, Xie L, Lu Y: Characterization of the cis elements in the proximal promoter regions of the anthocyanin pathway genes reveals a common regulatory logic that governs pathway regulation. J Exp Bot. 2015 Jul;66(13):3775-89. doi: 10.1093/jxb/erv173. Epub 2015 Apr 23. [PubMed:25911741 ]
Bindon K, Kassara S, Hayasaka Y, Schulkin A, Smith P: Properties of wine polymeric pigments formed from anthocyanin and tannins differing in size distribution and subunit composition. J Agric Food Chem. 2014 Nov 26;62(47):11582-93. doi: 10.1021/jf503922h. Epub 2014 Nov 17. [PubMed:25356846 ]
Kamiya, K., et al. (2001). Kamiya, K., et al, Chem. Pharm. Bull. 49, 551 (2001). Chem. Pharm. Bull..

Showing NP-Card for Proanthocyanidin A-6 (NP0025690)

MOL for NP0025690 (Proanthocyanidin A-6)

3D MOL for NP0025690 (Proanthocyanidin A-6)

3D SDF for NP0025690 (Proanthocyanidin A-6)

3D-SDF for NP0025690 (Proanthocyanidin A-6)

PDB for NP0025690 (Proanthocyanidin A-6)

3D PDB for NP0025690 (Proanthocyanidin A-6)

SMILES for NP0025690 (Proanthocyanidin A-6)

INCHI for NP0025690 (Proanthocyanidin A-6)

Structure for NP0025690 (Proanthocyanidin A-6)

3D Structure for NP0025690 (Proanthocyanidin A-6)