NP-MRD: Showing NP-Card for (1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol (NP0157592)

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Record Information

Version

2.0

Created at

2022-09-02 15:00:37 UTC

Updated at

2022-09-02 15:00:37 UTC

NP-MRD ID

NP0157592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

Description

Isovaticanol B belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol is found in Upuna borneensis. Based on a literature review very few articles have been published on Isovaticanol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217002D          

 68 79  0  0  1  0            999 V2000
    4.2484   -3.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7052   -2.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -3.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3461   -2.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -1.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0487   -1.0577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2289   -1.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0775    0.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133    1.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311    1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3178    0.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926    0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367   -0.2057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9824    0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733   -0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853   -0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5624    0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    2.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    0.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615    1.5988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0245    2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9275    3.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506    3.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884    4.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8476    2.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    1.6044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3069    2.2977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5492    3.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    3.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297    4.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    4.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    5.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956    4.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244    2.0364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1470    2.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    3.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    3.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    4.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4897    3.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    2.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8979    2.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1464    1.3876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6561    0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636    0.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540    0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636    0.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246   -0.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4952   -0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904   -1.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714    1.3809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4509    0.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092   -0.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172   -1.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7515    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2720    0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327    2.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -1.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599   -2.1119    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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
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 28 29  1  0  0  0  0
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 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 13  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
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 33 41  1  0  0  0  0
 12 41  1  0  0  0  0
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 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 42 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  6  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 50 57  1  0  0  0  0
 49 58  1  0  0  0  0
 58 59  1  6  0  0  0
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 60 61  1  0  0  0  0
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 62 63  1  0  0  0  0
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 58 66  1  0  0  0  0
 47 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

110121  0  0  0  0  0  0  0  0999 V2000
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   -3.9403   -4.2166   -2.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022217002D          

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M  END
> <DATABASE_ID>
NP0157592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1OC2=CC(O)=C3[C@H]([C@@H]([C@H]4[C@@H](C5=CC=C(O)C=C5)C5=C(O)C=C(O)C=C5[C@H]1C2=C34)C1=CC=C(O)C=C1)C1=CC(O)=CC2=C1[C@@H]([C@@H](O2)C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C56H42O12/c57-30-9-1-25(2-10-30)44-47-38(20-36(63)22-40(47)65)50-52-43(68-56(50)28-7-15-33(60)16-8-28)24-41(66)51-49(45(53(44)54(51)52)26-3-11-31(58)12-4-26)39-21-37(64)23-42-48(39)46(29-17-34(61)19-35(62)18-29)55(67-42)27-5-13-32(59)14-6-27/h1-24,44-46,49-50,53,55-66H/t44-,45-,46-,49-,50-,53+,55-,56+/m0/s1

> <INCHI_KEY>
VOANMQWFRWOKSM-VMHVPZBPSA-N

> <FORMULA>
C56H42O12

> <MOLECULAR_WEIGHT>
906.94

> <EXACT_MASS>
906.267626792

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
94.07184732966813

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
10.430361719333334

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.04817570963634

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.658839429049285

> <JCHEM_PKA_STRONGEST_BASIC>
-5.453814655210164

> <JCHEM_POLAR_SURFACE_AREA>
220.75999999999996

> <JCHEM_REFRACTIVITY>
253.1099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       7.930  -6.645   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.916  -5.407   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.410  -5.727   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.379  -4.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.855  -3.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.824  -1.974   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.294  -2.148   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.656  -0.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.188  -0.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.145   1.222   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.145   2.551   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.991   2.261   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.460   1.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.159   0.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.175  -0.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.567   0.275   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.689  -0.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.164  -0.336   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.679  -0.914   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.516   1.163   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.395   2.218   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.089   3.893   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.920   1.774   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.968   2.984   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.646   4.367   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   5.646   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.465   7.028   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.001   7.133   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.192   8.281   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.860   5.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.182   4.472   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.428   2.995   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.440   4.289   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.892   5.761   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.843   6.889   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.295   8.361   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.796   8.705   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.833  10.339   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.845   7.578   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.393   6.106   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.979   3.801   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.274   4.696   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.126   6.229   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.379   7.124   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.809   8.696   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -2.781   6.486   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.929   4.954   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.676   4.059   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.140   2.590   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.225   1.352   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.305   1.525   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       1.221   0.287   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       2.732   0.892   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.606  -1.125   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.924  -1.299   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -1.475  -2.877   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -1.840  -0.060   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.680   2.578   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -4.575   1.324   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -3.937  -0.077   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -4.832  -1.331   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -6.365  -1.182   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -7.312  -2.474   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -7.003   0.220   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -6.108   1.473   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -4.168   4.038   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       6.361  -2.798   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       7.392  -3.942   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   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   41                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14    6   16                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   24   13   33                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34                                                       
CONECT   41   33   12   42                                                  
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   66                                                  
CONECT   48   47   42   49                                                  
CONECT   49   48   50   58                                                  
CONECT   50   49   51   57                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   50                                                       
CONECT   58   49   59   66                                                  
CONECT   59   58   60   65                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   59                                                       
CONECT   66   58   47                                                       
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,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1OC2=CC(O)=C3[C@H]([C@@H]([C@H]4[C@@H](C5=CC=C(O)C=C5)C5=C(O)C=C(O)C=C5[C@H]1C2=C34)C1=CC=C(O)C=C1)C1=CC(O)=CC2=C1[C@@H]([C@@H](O2)C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C56H42O12/c57-30-9-1-25(2-10-30)44-47-38(20-36(63)22-40(47)65)50-52-43(68-56(50)28-7-15-33(60)16-8-28)24-41(66)51-49(45(53(44)54(51)52)26-3-11-31(58)12-4-26)39-21-37(64)23-42-48(39)46(29-17-34(61)19-35(62)18-29)55(67-42)27-5-13-32(59)14-6-27/h1-24,44-46,49-50,53,55-66H/t44-,45-,46-,49-,50-,53+,55-,56+/m0/s1

InChI Key

VOANMQWFRWOKSM-VMHVPZBPSA-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
4-prenylated 2-arybenzofuran
Linear 1,7-diphenylheptane skeleton
Neolignan skeleton
Dibenzocycloheptene
1-phenylcoumaran
Stilbene
Benzofuran
Indane
Coumaran
Resorcinol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Organoheterocyclic compound
Polyol
Oxacycle
Ether
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	6.13	ALOGPS
logP	10.43	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	8.66	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	94.07 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

Not Available

Chemspider ID

10286765

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21674273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol (NP0157592)

MOL for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

3D MOL for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

3D SDF for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

3D-SDF for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

PDB for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

3D PDB for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

SMILES for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

INCHI for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

Structure for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)

3D Structure for NP0157592 ((1s,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol)