NP-MRD: Showing NP-Card for (1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol (NP0316669)

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Record Information

Version

2.0

Created at

2022-09-11 16:00:49 UTC

Updated at

2022-09-11 16:00:50 UTC

NP-MRD ID

NP0316669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol

Description

(1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol is found in Sophora davidii. Based on a literature review very few articles have been published on (1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112218002D          

 52 59  0  0  1  0            999 V2000
    6.5285   -0.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0436   -0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -0.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8438    2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    3.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    2.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6837    3.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    4.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    5.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    4.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764    3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089    2.6896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6434    2.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5257    1.9764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528    3.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009    4.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192    4.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893    5.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075    6.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1411    5.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    4.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6231   -0.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409    3.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    3.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4148    3.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    1.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792    0.6563    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  6  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
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  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  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 34 41  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 43 49  1  0  0  0  0
 42 50  1  0  0  0  0
 31 50  1  0  0  0  0
  5 51  1  0  0  0  0
 51 52  2  0  0  0  0
  2 52  1  0  0  0  0
M  END


  Mrv1652309112218002D          

 52 59  0  0  1  0            999 V2000
    6.5285   -0.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0436   -0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -0.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8438    2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    3.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    2.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6837    3.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    4.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    5.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    4.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764    3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089    2.6896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6434    2.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5257    1.9764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528    3.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009    4.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192    4.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893    5.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075    6.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1411    5.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    4.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6231   -0.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409    3.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    3.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4148    3.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    1.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792    0.6563    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  6  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
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  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  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 34 41  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 43 49  1  0  0  0  0
 42 50  1  0  0  0  0
 31 50  1  0  0  0  0
  5 51  1  0  0  0  0
 51 52  2  0  0  0  0
  2 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]([C@H]1[C@@H]([C@H](C2=C(O)C=C(O)C=C12)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)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C42H34O10/c43-24-7-1-20(2-8-24)35-37-31(16-29(48)18-33(37)50)40(41(51)21-3-9-25(44)10-4-21)39(35)32-17-30(49)19-34-38(32)36(23-13-27(46)15-28(47)14-23)42(52-34)22-5-11-26(45)12-6-22/h1-19,35-36,39-51H/t35-,36+,39+,40+,41-,42-/m0/s1

> <INCHI_KEY>
UAFPJINRIKXWOZ-DFBZKPFLSA-N

> <FORMULA>
C42H34O10

> <MOLECULAR_WEIGHT>
698.724

> <EXACT_MASS>
698.215197295

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
70.72943764481249

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <JCHEM_LOGP>
7.271823545666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.085468830447068

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.689541145137925

> <JCHEM_PKA_STRONGEST_BASIC>
-5.451928030486735

> <JCHEM_POLAR_SURFACE_AREA>
191.29999999999998

> <JCHEM_REFRACTIVITY>
193.37889999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0      12.187  -1.428   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.281  -0.182   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.750  -0.343   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.845   0.903   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.471   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.566   3.556   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.042   5.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.449   5.647   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.028   5.583   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.610   7.178   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.364   8.084   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.646   9.659   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.172   7.491   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.796   5.926   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.550   5.021   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.934   5.304   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.715   3.689   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.765   7.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.362   7.637   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.209   9.169   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.460  10.068   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.307  11.600   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.863   9.434   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.016   7.901   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.026   3.556   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.630  -1.095   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.340   3.801   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.864   5.265   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.636   5.985   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.895   6.410   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.401   6.090   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.641   7.165   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -3.796   0.735   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      11.003   2.471   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.908   1.225   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7   25                                                  
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   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   15    6   26                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   50                                                  
CONECT   32   31   26   33                                                  
CONECT   33   32   34   42                                                  
CONECT   34   33   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34                                                       
CONECT   42   33   43   50                                                  
CONECT   43   42   44   49                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   43                                                       
CONECT   50   42   31                                                       
CONECT   51    5   52                                                       
CONECT   52   51    2                                                       
MASTER        0    0    0    0    0    0    0    0   52    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₃₄O₁₀

Average Mass

698.7240 Da

Monoisotopic Mass

698.21520 Da

IUPAC Name

(1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

(1S,2R,3S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(R)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

CAS Registry Number

Not Available

SMILES

O[C@H]([C@H]1[C@@H]([C@H](C2=C(O)C=C(O)C=C12)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)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C42H34O10/c43-24-7-1-20(2-8-24)35-37-31(16-29(48)18-33(37)50)40(41(51)21-3-9-25(44)10-4-21)39(35)32-17-30(49)19-34-38(32)36(23-13-27(46)15-28(47)14-23)42(52-34)22-5-11-26(45)12-6-22/h1-19,35-36,39-51H/t35-,36+,39+,40+,41-,42-/m0/s1

InChI Key

UAFPJINRIKXWOZ-DFBZKPFLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sophora davidii	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
Linear 1,7-diphenylheptane skeleton
1-phenylcoumaran
Stilbene
Indane
Coumaran
Resorcinol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
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	7.27	ChemAxon
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	191.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	193.38 m³·mol⁻¹	ChemAxon
Polarizability	70.73 Å³	ChemAxon
Number of Rings	8	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

162907359

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,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol (NP0316669)

MOL for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D MOL for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D SDF for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D-SDF for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

PDB for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D PDB for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

SMILES for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

INCHI for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

Structure for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D Structure for NP0316669 ((1s,2r,3s)-2-[(2r,3r)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-1-[(r)-hydroxy(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)