NP-MRD: Showing NP-Card for (1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol (NP0239719)

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Record Information

Version

2.0

Created at

2022-09-06 23:22:19 UTC

Updated at

2022-09-06 23:22:19 UTC

NP-MRD ID

NP0239719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol

Description

Vaticanol C belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol was first documented in 2010 (PMID: 20735051). Based on a literature review a small amount of articles have been published on vaticanol C (PMID: 28928759) (PMID: 32581406) (PMID: 21510709) (PMID: 21212619).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201222D          

 68 79  0  0  1  0            999 V2000
   -0.1520    0.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072    1.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8451    2.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802    2.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    3.1031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1852    2.5355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6889    3.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    2.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766    3.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8798    4.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    4.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6312    5.3272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921    3.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    4.3358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7295    5.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    5.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7024    6.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4235    6.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0057    3.9656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8354    3.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2392    1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    0.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4118    4.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3119    3.0800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.6304    3.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0913    2.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6575    2.3278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.6007    1.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3705    0.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0067   -0.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4503    1.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4951    0.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351   -0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358    0.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040    0.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257    1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    1.2397    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  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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  6 23  1  0  0  0  0
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 29 48  1  0  0  0  0
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  9 58  1  0  0  0  0
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  5 67  1  0  0  0  0
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  2 68  1  0  0  0  0
M  END

     RDKit          3D

110121  0  0  0  0  0  0  0  0999 V2000
    1.5757    0.8299   -6.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    0.5020   -4.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    1.4052   -3.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778    0.9980   -2.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.2526   -2.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555   -0.6511   -1.0878 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.0216   -0.9406    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072201222D          

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M  END
> <DATABASE_ID>
NP0239719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=CC(O)=C3[C@H]([C@H]4[C@@H]([C@H](C5=C4C4=C(O[C@H]([C@@H]4C4=CC(O)=CC(O)=C4)C4=CC=C(O)C=C4)C=C5O)C3=C2[C@H]1C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C56H42O12/c57-31-9-1-25(2-10-31)43-47-39(65)23-41-49(45(29-17-35(61)21-36(62)18-29)55(67-41)27-5-13-33(59)14-6-27)53(47)52-44(26-3-11-32(58)12-4-26)51(43)54-48(52)40(66)24-42-50(54)46(30-19-37(63)22-38(64)20-30)56(68-42)28-7-15-34(60)16-8-28/h1-24,43-46,51-52,55-66H/t43-,44+,45-,46-,51+,52-,55+,56+/m1/s1

> <INCHI_KEY>
DTAYOOZOCCYGJM-FCMAYUGISA-N

> <FORMULA>
C56H42O12

> <MOLECULAR_WEIGHT>
906.94

> <EXACT_MASS>
906.267626792

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
93.74083660184104

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,11R,12R,15R,16R,22S)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0^{2,10}.0^{3,7}.0^{13,21}.0^{14,18}]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol

> <JCHEM_LOGP>
10.430361719333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.03402908781441

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.636779447216927

> <JCHEM_PKA_STRONGEST_BASIC>
-5.48835617819729

> <JCHEM_POLAR_SURFACE_AREA>
220.75999999999996

> <JCHEM_REFRACTIVITY>
253.1099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,11R,12R,15R,16R,22S)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0^{2,10}.0^{3,7}.0^{13,21}.0^{14,18}]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.284   1.668   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.947   2.853   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.692   4.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.578   5.039   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.323   4.813   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.511   5.793   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.946   4.733   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.886   5.953   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.365   5.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.476   6.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.109   8.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.630   8.514   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.645   9.944   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.519   7.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.120   8.093   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.095   9.633   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.749  10.381   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.724  11.921   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.044  12.713   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.173  14.334   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.391  11.965   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.416  10.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.744   7.403   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.426   5.896   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.406   4.708   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.180   2.962   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.242   1.136   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.348   3.011   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.368   4.199   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.907   5.641   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.702   6.600   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.769   8.138   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.530   8.965   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.464  10.504   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.564  11.708   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.902  11.215   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.201  10.388   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.740  11.761   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.134   8.850   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.582   5.749   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.025   6.288   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -3.213   5.309   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.656   5.848   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.910   7.366   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -6.447   7.827   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -3.722   8.346   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.279   7.807   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -0.170   4.265   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      10.833   5.861   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      10.561   4.345   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.627   3.234   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.122   3.601   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      14.188   2.490   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      13.758   1.011   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      14.946  -0.068   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.263   0.643   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      11.197   1.755   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       9.035   4.136   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       8.307   2.779   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       9.119   1.470   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.391   0.113   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       8.839  -1.455   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       6.852   0.065   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       6.040   1.374   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       5.048   0.146   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       6.768   2.731   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       3.578   3.294   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       2.389   2.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   68                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   67                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   58                                                  
CONECT   10    9   11   49                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16                                                       
CONECT   23   15    6   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24    7   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   48                                                  
CONECT   30   29   24   31                                                  
CONECT   31   30   32   40                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   31   41   48                                                  
CONECT   41   40   42   47                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   41                                                       
CONECT   48   40   29                                                       
CONECT   49   10   50                                                       
CONECT   50   49   51   58                                                  
CONECT   51   50   52   57                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   51                                                       
CONECT   58   50    9   59                                                  
CONECT   59   58   60   66                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   59                                                       
CONECT   67    5   68                                                       
CONECT   68   67    2                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  158    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₆H₄₂O₁₂

Average Mass

906.9400 Da

Monoisotopic Mass

906.26763 Da

IUPAC Name

(1S,4R,5R,11R,12R,15R,16R,22S)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0^{2,10}.0^{3,7}.0^{13,21}.0^{14,18}]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=CC(O)=C3[C@H]([C@H]4[C@@H]([C@H](C5=C4C4=C(O[C@H]([C@@H]4C4=CC(O)=CC(O)=C4)C4=CC=C(O)C=C4)C=C5O)C3=C2[C@H]1C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C56H42O12/c57-31-9-1-25(2-10-31)43-47-39(65)23-41-49(45(29-17-35(61)21-36(62)18-29)55(67-41)27-5-13-33(59)14-6-27)53(47)52-44(26-3-11-32(58)12-4-26)51(43)54-48(52)40(66)24-42-50(54)46(30-19-37(63)22-38(64)20-30)56(68-42)28-7-15-34(60)16-8-28/h1-24,43-46,51-52,55-66H/t43-,44+,45-,46-,51+,52-,55+,56+/m1/s1

InChI Key

DTAYOOZOCCYGJM-FCMAYUGISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4-prenylated 2-arybenzofuran
Linear 1,7-diphenylheptane skeleton
1-aryltetralin lignan
Neolignan skeleton
Phenylnaphthalene
Dibenzocycloheptene
1-phenylcoumaran
Stilbene
Naphthofuran
Tetralin
Benzofuran
Indane
Coumaran
Resorcinol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	10.43	ChemAxon
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	220.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	253.11 m³·mol⁻¹	ChemAxon
Polarizability	93.74 Å³	ChemAxon
Number of Rings	12	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

C00037981

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

101053432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chitarrini G, Soini E, Riccadonna S, Franceschi P, Zulini L, Masuero D, Vecchione A, Stefanini M, Di Gaspero G, Mattivi F, Vrhovsek U: Identification of Biomarkers for Defense Response to Plasmopara viticola in a Resistant Grape Variety. Front Plant Sci. 2017 Sep 5;8:1524. doi: 10.3389/fpls.2017.01524. eCollection 2017. [PubMed:28928759 ]
Inoue C, Sobue S, Mizutani N, Kawamoto Y, Nishizawa Y, Ichihara M, Takeuchi T, Hayakawa F, Suzuki M, Ito T, Nozawa Y, Murate T: Vaticanol C, a phytoalexin, induces apoptosis of leukemia and cancer cells by modulating expression of multiple sphingolipid metabolic enzymes. Nagoya J Med Sci. 2020 May;82(2):261-280. doi: 10.18999/nagjms.82.2.261. [PubMed:32581406 ]
Mattivi F, Vrhovsek U, Malacarne G, Masuero D, Zulini L, Stefanini M, Moser C, Velasco R, Guella G: Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling x Teroldego) genotypes infected with Plasmopara viticola. J Agric Food Chem. 2011 May 25;59(10):5364-75. doi: 10.1021/jf200771y. Epub 2011 May 3. [PubMed:21510709 ]
Ito T: [Structures of oligostilbenoids in dipterocarpaceaeous plants and their biological activities]. Yakugaku Zasshi. 2011 Jan;131(1):93-100. doi: 10.1248/yakushi.131.93. [PubMed:21212619 ]
Abe N, Ito T, Ohguchi K, Nasu M, Masuda Y, Oyama M, Nozawa Y, Ito M, Iinuma M: Resveratrol oligomers from Vatica albiramis. J Nat Prod. 2010 Sep 24;73(9):1499-506. doi: 10.1021/np1002675. [PubMed:20735051 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol (NP0239719)

MOL for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

3D MOL for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

3D SDF for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

3D-SDF for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

PDB for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

3D PDB for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

SMILES for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

INCHI for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

Structure for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)

3D Structure for NP0239719 ((1s,4r,5r,11r,12r,15r,16r,22s)-4,15-bis(3,5-dihydroxyphenyl)-5,11,16,22-tetrakis(4-hydroxyphenyl)-6,17-dioxahexacyclo[10.9.1.0²,¹⁰.0³,⁷.0¹³,²¹.0¹⁴,¹⁸]docosa-2,7,9,13(21),14(18),19-hexaene-9,20-diol)