NP-MRD: Showing NP-Card for (1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol (NP0196966)

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Record Information

Version

2.0

Created at

2022-09-04 15:08:51 UTC

Updated at

2022-09-04 15:08:51 UTC

NP-MRD ID

NP0196966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

Description

Upunaphenol O belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol is found in Upuna borneensis. Based on a literature review very few articles have been published on Upunaphenol O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217082D          

 68 78  0  0  1  0            999 V2000
    2.7333   -3.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719   -2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575   -0.8171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7623   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514    1.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183    0.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0804    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4986    1.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5166    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3151   -0.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.8294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0857   -1.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360   -1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829   -2.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -1.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010   -1.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3696   -2.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444   -2.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6661   -2.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1409   -1.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5382   -3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165   -3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3924   -4.2028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5881   -4.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6613   -3.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795   -4.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -5.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2976   -6.1469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0137   -4.7455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9399   -5.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913   -5.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175   -6.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7922   -7.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7183   -8.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5407   -6.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6145   -6.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7219   -4.3223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108   -0.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184    1.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2832    2.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    3.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4588    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    4.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    2.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   -1.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.3424    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  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
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 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
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 38 39  1  1  0  0  0
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 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 39 46  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  6  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  2  0  0  0  0
 48 54  1  0  0  0  0
 47 55  1  0  0  0  0
 36 55  1  0  0  0  0
 28 56  1  0  0  0  0
 56 57  2  0  0  0  0
 25 57  1  0  0  0  0
 17 58  1  0  0  0  0
 58 59  1  0  0  0  0
 15 59  1  0  0  0  0
 59 60  1  1  0  0  0
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 61 62  1  0  0  0  0
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 63 64  1  0  0  0  0
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 65 66  2  0  0  0  0
 60 66  1  0  0  0  0
  5 67  1  0  0  0  0
 67 68  2  0  0  0  0
  2 68  1  0  0  0  0
M  END

     RDKit          3D

110120  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309042217082D          

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M  END
> <DATABASE_ID>
NP0196966

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=C([C@H]1C1=CC(O)=CC(O)=C1)C(\C=C\C1=CC=C(O[C@H]3[C@H](C4=CC=C(O)C=C4)C4=C(O)C=C(O)C=C4[C@H]4[C@@H](OC5=C4C3=CC(O)=C5)C3=CC=C(O)C=C3)C=C1)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C56H42O12/c57-34-11-5-29(6-12-34)49-51-43(23-40(63)25-45(51)65)53-52-44(24-41(64)27-47(52)68-55(53)31-9-15-36(59)16-10-31)56(49)66-42-17-2-28(3-18-42)1-4-32-19-39(62)26-46-48(32)50(33-20-37(60)22-38(61)21-33)54(67-46)30-7-13-35(58)14-8-30/h1-27,49-50,53-65H/b4-1+/t49-,50-,53-,54+,55+,56-/m1/s1

> <INCHI_KEY>
JSQVCLZFBPQVBY-UVPGZANQSA-N

> <FORMULA>
C56H42O12

> <MOLECULAR_WEIGHT>
906.94

> <EXACT_MASS>
906.267626792

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
92.94047082529502

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8R,9S,16R)-9-{4-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

> <JCHEM_LOGP>
11.076701637333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.913572836672179

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.502969794414996

> <JCHEM_PKA_STRONGEST_BASIC>
-5.467487037522489

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
255.20749999999987

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,9S,16R)-9-{4-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       5.102  -7.035   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.413  -5.658   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.876  -5.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.188  -4.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.036  -2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.347  -1.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.290  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.768  -0.739   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.133  -2.235   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.881   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.516   1.821   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.629   2.885   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.038   2.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.925   1.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.527   1.837   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.150   1.148   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.931   2.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.421   1.858   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.831   0.373   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.322  -0.014   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.750  -0.724   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.170  -0.358   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.808  -1.548   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.160  -2.945   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.374  -3.083   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.021  -4.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.555  -4.618   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.441  -3.359   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.975  -3.497   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.623  -4.894   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.157  -5.032   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.043  -3.772   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.577  -3.910   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -11.463  -2.651   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -11.224  -5.308   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.338  -6.567   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.804  -6.429   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.199  -7.845   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.698  -8.188   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.650  -7.059   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.149  -7.402   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.101  -6.273   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.695  -8.874   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.743 -10.003   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -4.289 -11.474   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -6.244  -9.660   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.359  -8.858   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -9.221 -10.392   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -7.824 -11.040   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -7.686 -12.573   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -8.945 -13.460   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -8.808 -14.994   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -10.343 -12.812   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -10.480 -11.278   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -10.681  -8.068   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -3.794  -1.962   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -2.260  -1.824   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -0.221   3.612   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       1.298   3.359   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       2.395   4.440   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       2.008   5.930   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       3.105   7.011   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       4.590   6.601   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       5.687   7.682   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       4.977   5.111   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       3.880   4.030   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.573  -2.995   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       5.262  -4.372   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   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14   16   59                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   58                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   57                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   56                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   55                                                  
CONECT   37   36   31   38                                                  
CONECT   38   37   39   47                                                  
CONECT   39   38   40   46                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   39                                                       
CONECT   47   38   48   55                                                  
CONECT   48   47   49   54                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   48                                                       
CONECT   55   47   36                                                       
CONECT   56   28   57                                                       
CONECT   57   56   25                                                       
CONECT   58   17   59                                                       
CONECT   59   58   15   60                                                  
CONECT   60   59   61   66                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66                                                       
CONECT   66   65   60                                                       
CONECT   67    5   68                                                       
CONECT   68   67    2                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  156    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₆H₄₂O₁₂

Average Mass

906.9400 Da

Monoisotopic Mass

906.26763 Da

IUPAC Name

(1R,8R,9S,16R)-9-{4-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=C([C@H]1C1=CC(O)=CC(O)=C1)C(\C=C\C1=CC=C(O[C@H]3[C@H](C4=CC=C(O)C=C4)C4=C(O)C=C(O)C=C4[C@H]4[C@@H](OC5=C4C3=CC(O)=C5)C3=CC=C(O)C=C3)C=C1)=CC(O)=C2

InChI Identifier

InChI=1S/C56H42O12/c57-34-11-5-29(6-12-34)49-51-43(23-40(63)25-45(51)65)53-52-44(24-41(64)27-47(52)68-55(53)31-9-15-36(59)16-10-31)56(49)66-42-17-2-28(3-18-42)1-4-32-19-39(62)26-46-48(32)50(33-20-37(60)22-38(61)21-33)54(67-46)30-7-13-35(58)14-8-30/h1-27,49-50,53-65H/b4-1+/t49-,50-,53-,54+,55+,56-/m1/s1

InChI Key

JSQVCLZFBPQVBY-UVPGZANQSA-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
Upuna borneensis	LOTUS Database	35616633

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
1-phenylcoumaran
Dibenzocycloheptene
Stilbene
Coumaran
Phenoxy compound
Phenol ether
Resorcinol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Organoheterocyclic compound
Oxacycle
Polyol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	11.08	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-5.5	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	8	ChemAxon
Refractivity	255.21 m³·mol⁻¹	ChemAxon
Polarizability	92.94 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

102424431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol (NP0196966)

MOL for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

3D MOL for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

3D SDF for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

3D-SDF for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

PDB for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

3D PDB for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

SMILES for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

INCHI for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

Structure for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)

3D Structure for NP0196966 ((1r,8r,9s,16r)-9-{4-[(1e)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy}-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol)