NP-MRD: Showing NP-Card for (1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0230446)

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Record Information

Version

2.0

Created at

2022-09-06 10:53:50 UTC

Updated at

2022-09-06 10:53:51 UTC

NP-MRD ID

NP0230446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Description

3,3',3'',4,4',4''-Hexahydro-2alpha,2'alpha,2''alpha-tris(3,4-dihydroxyphenyl)-2,7'-epoxy-4beta,8':4'Beta,8''-ter[2H-1-benzopyran]-3alpha,3'beta,3''alpha,5,5',5'',7,7''-octol 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''. (1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol is found in Aesculus hippocastanum. Based on a literature review very few articles have been published on 3,3',3'',4,4',4''-Hexahydro-2alpha,2'alpha,2''alpha-tris(3,4-dihydroxyphenyl)-2,7'-epoxy-4beta,8':4'Beta,8''-ter[2H-1-benzopyran]-3alpha,3'beta,3''alpha,5,5',5'',7,7''-octol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212532D          

 63 72  0  0  1  0            999 V2000
   -1.2726   12.1827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   11.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   11.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   10.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   10.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    9.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   10.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425   10.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    9.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    8.7962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1749    8.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906    7.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085    7.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108    8.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6287    8.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    9.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973    9.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771    9.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    8.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    7.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4331    6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    5.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    7.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4331    8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2196    9.0776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3234    9.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9298    9.9291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    8.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4248    8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1393    9.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7103    7.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4248    6.6307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9959    5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    5.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    4.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    4.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7103    4.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5682    7.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2827    6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972    7.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2827    5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972    5.3932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1393    4.5682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4248    4.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
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 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
 10 19  1  0  0  0  0
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 24 25  1  0  0  0  0
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 20 26  1  0  0  0  0
 27 26  1  6  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
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 61 63  1  0  0  0  0
 49 63  1  0  0  0  0
M  END

     RDKit          3D

 99108  0  0  0  0  0  0  0  0999 V2000
    3.0078    4.7022   -4.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296    3.5922   -3.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126    2.4089   -3.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7242    2.5985   -1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0097    2.0155    2.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309062212532D          

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 49 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C([C@@H]1[C@H](O)[C@H](OC3=C4[C@@H]5[C@@H](O)[C@@](OC6=CC(O)=CC(O)=C56)(OC4=CC(O)=C13)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38-,39+,40-,41-,44-,45+/m1/s1

> <INCHI_KEY>
BYSRPHRKESMCPO-RZYYSIBWSA-N

> <FORMULA>
C45H36O18

> <MOLECULAR_WEIGHT>
864.765

> <EXACT_MASS>
864.190164319

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
83.68240401033559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6S,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_LOGP>
4.911170094999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.014707025187052

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.597961065379815

> <JCHEM_PKA_STRONGEST_BASIC>
-5.217533055260987

> <JCHEM_POLAR_SURFACE_AREA>
320.14

> <JCHEM_REFRACTIVITY>
216.70460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.376  22.741   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.977  21.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.489  20.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.091  19.367   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.397  18.969   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.180  18.279   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  18.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.066  20.165   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  17.907   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.400  16.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.926  16.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.516  14.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.043  14.595   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.980  15.817   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.507  15.616   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.391  17.239   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.328  18.461   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.864  17.440   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.630  15.086   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.142  14.687   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.142  13.147   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.808  12.377   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.808  10.837   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.525  13.147   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.525  14.687   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.808  15.457   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.410  16.945   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.470  17.181   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.736  18.534   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.859  15.457   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.193  14.687   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.526  15.457   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.526  16.997   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.860  17.767   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.194  16.997   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.527  17.767   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.194  15.457   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.527  14.687   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.860  14.687   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.193  13.147   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.526  12.377   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.859  12.377   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.859  10.837   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.525  10.067   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.006   9.906   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       0.525   8.527   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.859   7.757   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.859   6.217   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       3.193   8.527   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.193  10.067   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.526  10.837   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.860  10.067   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.194  10.837   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       7.194  12.377   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.527  13.147   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       9.861  12.377   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      11.195  13.147   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       9.861  10.837   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      11.195  10.067   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       8.527  10.067   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.860   8.527   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       7.194   7.757   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       4.526   7.757   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   19   28                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19   10   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   42                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   20   27                                                  
CONECT   27   26    6   28                                                  
CONECT   28   27   10   29                                                  
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   31   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   24   43                                                  
CONECT   43   42   44   50                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   63                                                  
CONECT   50   49   43   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   61                                                  
CONECT   53   52   54   60                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   53                                                       
CONECT   61   52   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   49                                                       
MASTER        0    0    0    0    0    0    0    0   63    0  144    0
END

View in JSmol

Synonyms

Value	Source
3,3',3'',4,4',4''-Hexahydro-2a,2'a,2''alpha-tris(3,4-dihydroxyphenyl)-2,7'-epoxy-4b,8':4'b,8''-ter[2H-1-benzopyran]-3a,3'b,3''alpha,5,5',5'',7,7''-octol	Generator
3,3',3'',4,4',4''-Hexahydro-2α,2'α,2''alpha-tris(3,4-dihydroxyphenyl)-2,7'-epoxy-4β,8':4'β,8''-ter[2H-1-benzopyran]-3α,3'β,3''alpha,5,5',5'',7,7''-octol	Generator

Chemical Formula

C₄₅H₃₆O₁₈

Average Mass

864.7650 Da

Monoisotopic Mass

864.19016 Da

IUPAC Name

(1R,5R,6S,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C([C@@H]1[C@H](O)[C@H](OC3=C4[C@@H]5[C@@H](O)[C@@](OC6=CC(O)=CC(O)=C56)(OC4=CC(O)=C13)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C(O)C=C2O

InChI Identifier

InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38-,39+,40-,41-,44-,45+/m1/s1

InChI Key

BYSRPHRKESMCPO-RZYYSIBWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum	LOTUS Database	35616633

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

B-type proanthocyanidin
A-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
3'-hydroxyflavonoid
Flavan-3-ol
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Pyranochromene
1-benzopyran
Benzopyran
Chromane
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Ketal
Phenol
1-hydroxy-2-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	4.91	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	320.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	216.7 m³·mol⁻¹	ChemAxon
Polarizability	83.68 Å³	ChemAxon
Number of Rings	10	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

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

101915834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0230446)

MOL for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D MOL for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D SDF for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D-SDF for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

PDB for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D PDB for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

SMILES for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

INCHI for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

Structure for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D Structure for NP0230446 ((1r,5r,6s,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)