NP-MRD: Showing NP-Card for 4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol (NP0299727)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 11:43:22 UTC

Updated at

2022-09-10 11:43:22 UTC

NP-MRD ID

NP0299727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol

Description

4-{6-[4-(3,4-Dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. 4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol is found in Joannesia princeps. 4-{6-[4-(3,4-Dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171503362D          

 36 41  0  0  0  0            999 V2000
   -0.9028    7.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478    6.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999    5.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449    5.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    4.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2420    3.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010    3.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8560    3.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    4.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5589    5.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    6.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    6.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    6.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    7.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716    8.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266    9.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647    8.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126    8.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097    7.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240    1.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391    0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    1.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470   -0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499   -2.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -1.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640   -1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670   -0.4768    0.0000 C   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  2  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
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
M  END

     RDKit          3D

 62 67  0  0  0  0  0  0  0  0999 V2000
   -2.7350   -1.1245   -1.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -1.8162   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0118   -1.5495    0.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8443   -1.9339    1.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478   -1.0837    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -1.5488    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.6927    1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -1.2371    2.0786 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5070   -0.2517    2.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    0.1038    2.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.7329    1.0383 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8946    0.0117   -0.2483 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1888    0.4159   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2354    0.8852   -2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147    1.2884   -2.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941    1.2119   -1.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8119    1.6027   -2.5061 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5601    0.7451   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7355    0.6769    0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3450    0.3496   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -0.7405   -1.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2670   -1.5348   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -1.6762    0.9803 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4454    0.6060    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    1.0295    0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060    0.2141    0.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591    0.6439    0.3649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709   -0.0922    0.8443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5468    0.4143    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174    0.5271    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8511    1.0072    0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0172    1.3785   -0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2461    1.8643   -1.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9315    1.2606   -1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0941    1.6305   -2.7483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6946    0.7789   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387   -0.5765   -2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5518   -2.9104   -1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7099   -1.6515   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8910   -2.1593    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981   -2.5825    1.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6985   -2.1368    2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874    1.1702    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5474    0.1399    2.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8852   -1.3198    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    0.9587   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3199    0.9398   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167    1.6489   -3.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8228    1.9408   -3.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5955    0.9697   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3990   -0.0034    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2771   -1.0403   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -2.5224   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567   -2.7300    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040    1.2516    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391    2.0436    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293   -0.0046    1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5000    0.2392    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6726    1.0838    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9957    1.9263   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9883    1.9760   -3.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    0.7177   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 23  1  0
 23 22  1  0
 22 21  1  0
 21 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 28  3  1  0
 36 29  1  0
 23  8  1  0
 20 13  1  0
 26  5  1  0
 12 11  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  1
  6 41  1  0
 24 55  1  0
 25 56  1  0
 28 57  1  1
 30 58  1  0
 31 59  1  0
 33 60  1  0
 35 61  1  0
 36 62  1  0
  8 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  1
 23 54  1  1
 22 52  1  0
 22 53  1  0
 12 46  1  1
 14 47  1  0
 15 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
M  END


  Mrv1533004171503362D          

 36 41  0  0  0  0            999 V2000
   -0.9028    7.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478    6.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999    5.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449    5.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    4.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2420    3.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010    3.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8560    3.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    4.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5589    5.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    6.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    6.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    6.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    7.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716    8.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266    9.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647    8.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126    8.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097    7.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240    1.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391    0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    1.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851    0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470   -0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499   -2.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -1.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640   -1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670   -0.4768    0.0000 C   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  2  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
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299727

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC2=CC(=CC=C2OC1C1=CC=C(O)C(O)=C1)C1OCC2C1COC2C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O9/c28-10-24-27(14-2-5-19(30)21(32)8-14)36-22-6-3-15(9-23(22)35-24)26-17-12-33-25(16(17)11-34-26)13-1-4-18(29)20(31)7-13/h1-9,16-17,24-32H,10-12H2

> <INCHI_KEY>
RSGUJBLAYQHQGR-UHFFFAOYSA-N

> <FORMULA>
C27H26O9

> <MOLECULAR_WEIGHT>
494.496

> <EXACT_MASS>
494.157682417

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.172052343073105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{6-[4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.6530092060000006

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.51123317196403

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.909457871819923

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904141818384993

> <JCHEM_POLAR_SURFACE_AREA>
138.07000000000002

> <JCHEM_REFRACTIVITY>
127.3383

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{6-[4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0      -1.685  13.503   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.209  12.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.240  10.894   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.764   9.429   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.794   8.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.318   6.820   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.349   5.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.855   5.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.331   7.460   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.301   8.605   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.777  10.069   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.746  11.214   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.222  12.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.728  12.999   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.204  14.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.174  15.608   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.650  17.072   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.667  15.288   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.637  16.432   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.191  13.823   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.873   4.211   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.778   2.965   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.873   1.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.408   2.195   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.408   3.735   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.056   4.211   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.961   2.965   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.056   1.719   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.532   0.254   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.039  -0.066   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.514  -1.530   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.484  -2.675   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.960  -4.139   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.022  -2.355   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.053  -3.499   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.498  -0.890   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
CONECT   21    7   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆O₉

Average Mass

494.4960 Da

Monoisotopic Mass

494.15768 Da

IUPAC Name

4-{6-[4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol

Traditional Name

4-{6-[4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl}benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OCC1OC2=CC(=CC=C2OC1C1=CC=C(O)C(O)=C1)C1OCC2C1COC2C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H26O9/c28-10-24-27(14-2-5-19(30)21(32)8-14)36-22-6-3-15(9-23(22)35-24)26-17-12-33-25(16(17)11-34-26)13-1-4-18(29)20(31)7-13/h1-9,16-17,24-32H,10-12H2

InChI Key

RSGUJBLAYQHQGR-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
Joannesia princeps	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
Benzo-1,4-dioxane
Benzodioxane
Catechol
Furofuran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Para-dioxin
Oxolane
Ether
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen 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	2.67	ALOGPS
logP	2.65	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.34 m³·mol⁻¹	ChemAxon
Polarizability	51.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

74963247

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol (NP0299727)

MOL for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

3D MOL for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

3D SDF for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

3D-SDF for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

PDB for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

3D PDB for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

SMILES for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

INCHI for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

Structure for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)

3D Structure for NP0299727 (4-{4-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-hexahydrofuro[3,4-c]furan-1-yl}benzene-1,2-diol)