NP-MRD: Showing NP-Card for 5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol (NP0326111)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 07:23:17 UTC

Updated at

2022-09-12 07:23:18 UTC

NP-MRD ID

NP0326111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol

Description

Viniferifuran, also known as amurensin H, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Viniferifuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Viniferifuran has been detected, but not quantified in, alcoholic beverages and fruits. 5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol is found in Vitis vinifera. This could make viniferifuran a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307152D          

 34 38  0  0  0  0            999 V2000
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    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
    3.2789    2.0625    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
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   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
   -0.7676    1.1270    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
    3.9934    0.8250    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
    2.0769    2.4777    0.0000 C   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
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    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
    3.2789    1.2375    0.0000 C   0  0  0  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
    6.1368    1.2375    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
    0.4630    2.8207    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
    3.9934    0.0000    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  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
    6.8513    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    3.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   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
  4  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  2  0  0  0  0
 16  3  1  0  0  0  0
 17  5  2  0  0  0  0
 17  6  1  0  0  0  0
 18  4  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20  7  2  0  0  0  0
 20  8  1  0  0  0  0
 21  9  2  0  0  0  0
 21 10  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  2  0  0  0  0
 23 13  2  0  0  0  0
 23 14  1  0  0  0  0
 24 11  1  0  0  0  0
 24 15  2  0  0  0  0
 25 15  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  2  0  0  0  0
 27 19  1  0  0  0  0
 27 26  1  0  0  0  0
 28 17  1  0  0  0  0
 28 27  2  0  0  0  0
 29 20  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  1  0  0  0  0
 34 28  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    7.5254    1.0574    0.8399 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907    0.4444    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2435   -0.9074    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328   -1.5136    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8277   -0.8190    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082   -1.5293   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5085   -1.1105   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573    0.1597   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    0.8811   -1.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    2.1098   -2.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    2.8339   -3.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    2.6821   -2.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884    2.0104   -1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355    2.3562   -1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.4226   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4219    1.3252    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703    1.2556    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    1.1644    1.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9549    1.1402    1.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2133    1.0455    1.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8176    1.2088   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5357    1.3012   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439    0.3910   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -0.8309    0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766   -1.0634    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -2.2329    2.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437   -2.4716    3.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9174   -3.2098    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -3.0085    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122   -3.9623   -0.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -1.8293   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    0.7537   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    0.5048    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1281    1.1644    0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5425    2.0454    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1847   -1.4336    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490   -2.5912   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -2.5678    0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654   -1.8635   -0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1297    0.4338   -2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663    2.4856   -3.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    3.6537   -2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    1.2754    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122    1.1121    3.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6615    1.9009    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6964    1.1902   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.3556   -1.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -0.2925    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640   -2.9232    3.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391   -4.1426    2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2187   -3.9947   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -1.6886   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523    1.1163    0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366    2.2048    0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 32  2  0
 32 23  1  0
 23 15  2  0
 15 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
  5 33  1  0
 33 34  2  0
 34  2  1  0
 32  8  1  0
 22 16  1  0
 31 24  1  0
 14 13  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  6 38  1  0
  7 39  1  0
  9 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 27 49  1  0
 28 50  1  0
 30 51  1  0
 31 52  1  0
 33 53  1  0
 34 54  1  0
M  END


  Mrv0541 05061307152D          

 34 38  0  0  0  0            999 V2000
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    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
    3.2789    2.0625    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
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   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
   -0.7676    1.1270    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
    3.9934    0.8250    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
    2.0769    2.4777    0.0000 C   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
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    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
    3.2789    1.2375    0.0000 C   0  0  0  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
    6.1368    1.2375    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
    0.4630    2.8207    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
    3.9934    0.0000    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  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
    6.8513    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    3.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   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
  4  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  2  0  0  0  0
 16  3  1  0  0  0  0
 17  5  2  0  0  0  0
 17  6  1  0  0  0  0
 18  4  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20  7  2  0  0  0  0
 20  8  1  0  0  0  0
 21  9  2  0  0  0  0
 21 10  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  2  0  0  0  0
 23 13  2  0  0  0  0
 23 14  1  0  0  0  0
 24 11  1  0  0  0  0
 24 15  2  0  0  0  0
 25 15  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  2  0  0  0  0
 27 19  1  0  0  0  0
 27 26  1  0  0  0  0
 28 17  1  0  0  0  0
 28 27  2  0  0  0  0
 29 20  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  1  0  0  0  0
 34 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C/C2=CC(O)=CC3=C2C(=C(O3)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H20O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,29-33H/b4-1-

> <INCHI_KEY>
MTRJOEZPTJRJOB-RJRFIUFISA-N

> <FORMULA>
C28H20O6

> <MOLECULAR_WEIGHT>
452.4548

> <EXACT_MASS>
452.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.053998610918654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
6.168835491333333

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.876946052535954

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.312506853709769

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6793389864260435

> <JCHEM_POLAR_SURFACE_AREA>
114.29

> <JCHEM_REFRACTIVITY>
130.40829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788   2.310   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  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.340   3.801   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.895   6.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.864   5.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.401   6.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.789   1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.743   0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.642   5.585   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.431   7.234   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    4   16                                                       
CONECT    2    7   16                                                       
CONECT    3    8   16                                                       
CONECT    4    1   18                                                       
CONECT    5    9   17                                                       
CONECT    6   10   17                                                       
CONECT    7    2   20                                                       
CONECT    8    3   20                                                       
CONECT    9    5   21                                                       
CONECT   10    6   21                                                       
CONECT   11   18   24                                                       
CONECT   12   19   22                                                       
CONECT   13   19   23                                                       
CONECT   14   22   23                                                       
CONECT   15   24   25                                                       
CONECT   16    1    2    3                                                  
CONECT   17    5    6   28                                                  
CONECT   18    4   11   26                                                  
CONECT   19   12   13   27                                                  
CONECT   20    7    8   29                                                  
CONECT   21    9   10   30                                                  
CONECT   22   12   14   31                                                  
CONECT   23   13   14   32                                                  
CONECT   24   11   15   33                                                  
CONECT   25   15   26   34                                                  
CONECT   26   18   25   27                                                  
CONECT   27   19   26   28                                                  
CONECT   28   17   27   34                                                  
CONECT   29   20                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
CONECT   34   25   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Amurensin H	HMDB

Chemical Formula

C₂₈H₂₀O₆

Average Mass

452.4548 Da

Monoisotopic Mass

452.12599 Da

IUPAC Name

5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol

Traditional Name

5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C/C2=CC(O)=CC3=C2C(=C(O3)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C28H20O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,29-33H/b4-1-

InChI Key

MTRJOEZPTJRJOB-RJRFIUFISA-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
Vitis vinifera	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
2-phenylbenzofuran
Phenylbenzofuran
Stilbene
Benzofuran
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen 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	4.82	ALOGPS
logP	6.17	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	114.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.41 m³·mol⁻¹	ChemAxon
Polarizability	48.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033646

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011746

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

131751470

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol (NP0326111)

MOL for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

3D MOL for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

3D SDF for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

3D-SDF for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

PDB for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

3D PDB for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

SMILES for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

INCHI for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

Structure for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)

3D Structure for NP0326111 (5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(1z)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol)