NP-MRD: Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0250713)

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Record Information

Version

2.0

Created at

2022-09-07 13:37:58 UTC

Updated at

2022-09-07 13:37:58 UTC

NP-MRD ID

NP0250713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

Description

2-[(3,4-Dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). 2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one is found in Bidens pilosa. 2-[(3,4-Dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191520202D          

 32 35  0  0  0  0            999 V2000
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  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
    4.7079    1.2375    0.0000 O   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
    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
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  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    1.1270    0.0000 C   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
   -1.1801    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   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
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 12 26  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.0162    1.3594    0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    0.9465    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -0.4081    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -1.5380    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230   -1.6049    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1842   -2.3275   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5498   -2.4393   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253   -1.8477    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6209   -1.9762    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4881   -1.1324    1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1487   -0.5340    2.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051   -1.0164    1.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225   -0.2784    0.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5122    1.0467    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526    1.8289    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125    3.1945    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    3.8152    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    3.0057   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0528    3.6956   -0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309    1.6445   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8648    0.8930   -0.1258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    0.4056   -1.2381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7281    1.0436   -1.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    0.8363   -0.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0382    0.7845   -1.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0866    0.5805   -0.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -0.3365    0.3086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5322   -0.7566    1.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9437   -1.5056   -0.5176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8843   -1.9230   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635   -1.0790   -1.1851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6283   -1.7277   -0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4549   -2.4745    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820   -2.8156   -1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606   -2.9984   -1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0592   -1.5200    1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6369   -0.0026    3.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.4748    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943    3.8260    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    4.9120    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479    3.2623   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725    0.6495   -2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364    1.7366    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2403    1.7446   -1.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0750   -0.0057   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7021   -0.1001   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306   -0.1167    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -0.1538    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464   -2.3564    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3201   -2.7594   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -1.5349   -2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6308   -1.4669    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  3  2  1  0
  2  1  2  0
 22 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27 24  1  0
 14 20  1  0
 12  5  1  0
  2 15  1  0
 26 46  1  0
 25 44  1  0
 25 45  1  0
 24 43  1  1
 22 42  1  6
 19 41  1  0
 17 40  1  0
 16 39  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 31 51  1  6
 32 52  1  0
 29 49  1  1
 30 50  1  0
 27 47  1  1
 28 48  1  0
M  END


  Mrv1533004191520202D          

 32 35  0  0  0  0            999 V2000
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  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
    4.7079    1.2375    0.0000 O   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
    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
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  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    1.1270    0.0000 C   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
   -1.1801    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   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
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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
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 13 14  2  0  0  0  0
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 15 16  2  0  0  0  0
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 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 12 26  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=C(O)C=CC3=C2OC(=CC2=CC=C(O)C(O)=C2)C3=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-14-16(27)17(28)18(29)21(31-14)32-20-11(24)4-2-9-15(26)13(30-19(9)20)6-8-1-3-10(23)12(25)5-8/h1-6,14,16-18,21-25,27-29H,7H2

> <INCHI_KEY>
WDGSPYHJXBEAQC-UHFFFAOYSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.301336636486475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
-0.28005506366666705

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.899888317119277

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.008165451686969

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662200164

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.1143

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.203   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.433   4.771   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.203   6.105   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.107   4.771   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.877   6.105   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.877   3.437   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   15   26                                                       
CONECT   26   25    7   12                                                  
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

Traditional Name

2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=C(O)C=CC3=C2OC(=CC2=CC=C(O)C(O)=C2)C3=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-14-16(27)17(28)18(29)21(31-14)32-20-11(24)4-2-9-15(26)13(30-19(9)20)6-8-1-3-10(23)12(25)5-8/h1-6,14,16-18,21-25,27-29H,7H2

InChI Key

WDGSPYHJXBEAQC-UHFFFAOYSA-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
Bidens pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzofuran
Coumaran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Primary alcohol
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
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	0.61	ALOGPS
logP	-0.28	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.11 m³·mol⁻¹	ChemAxon
Polarizability	42.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74819305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0250713)

MOL for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D MOL for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D SDF for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D-SDF for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

PDB for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D PDB for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

SMILES for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

INCHI for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

Structure for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D Structure for NP0250713 (2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)