NP-MRD: Showing NP-Card for (2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0247730)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 09:41:24 UTC

Updated at

2022-09-07 09:41:24 UTC

NP-MRD ID

NP0247730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

Description

Tomentodiplacol belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. (2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one is found in Paulownia tomentosa. (2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one was first documented in 2007 (PMID: 17625893). Based on a literature review very few articles have been published on tomentodiplacol (PMID: 25735399).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211412D          

 34 36  0  0  1  0            999 V2000
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
 24 34  1  0  0  0  0
 16 34  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -8.3303   -0.5493   -1.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9482   -1.7876   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9539   -2.8698   -1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5176   -2.1048   -1.3930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3335   -2.5353   -0.0699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -0.9032   -1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999   -1.3303   -1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3760   -0.0799   -1.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983    0.5576   -2.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6735    0.3710   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8141    1.5625   -0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    1.2300   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911    0.5991   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.2954   -2.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    0.2848   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100    0.6008    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128    1.2313    1.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901    1.5443    1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    2.1678    1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    1.5500    2.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407    2.2000    3.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415    1.1138    3.0310 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8717    1.9178    4.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790    1.1020    1.8005 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5495    0.6140    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    0.3744    3.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4945   -0.0927    3.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937   -0.3253    1.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5027   -0.7899    1.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5568   -0.0831    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2155   -0.3002   -0.4150 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5693   -0.0521   -1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2609    0.3767    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    0.2992    0.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3855   -0.3527   -2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6433    0.2726   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4372   -3.8498   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7487   -2.7701   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3731   -2.7861   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1805   -2.9119   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2215   -2.6086    0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7555   -0.3966   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8805   -0.1319   -0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476   -2.0536   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591   -1.7271   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021    1.2443   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3676    1.1347   -2.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171   -0.2411   -3.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7162   -0.1747    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916    2.2787    0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    2.1144   -1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4854   -0.1887   -3.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3113   -0.2087   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    2.4958    2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    0.0434    3.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516    2.5859    3.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527    2.1376    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6778    0.5355    4.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9892   -0.2801    4.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9092   -0.9565    2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1387    0.9740   -1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3382   -0.1288   -2.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7659   -0.7935   -1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7908    0.5548   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 30  1  0
 30 33  2  0
 33 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 25 24  1  0
 24 34  1  0
 34 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 12 18  1  0
 18 19  1  0
 18 17  2  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 28 30  1  0
 22 24  1  0
 17 16  1  0
 32 61  1  0
 32 62  1  0
 32 63  1  0
 33 64  1  0
 26 58  1  0
 27 59  1  0
 29 60  1  0
 24 57  1  6
 15 53  1  0
 14 52  1  0
 11 50  1  0
 11 51  1  0
 10 49  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
  7 44  1  0
  7 45  1  0
  6 42  1  0
  6 43  1  0
  4 40  1  6
  5 41  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  1 35  1  0
  1 36  1  0
 19 54  1  0
 22 55  1  1
 23 56  1  0
M  END


  Mrv1652309072211412D          

 34 36  0  0  1  0            999 V2000
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
 24 34  1  0  0  0  0
 16 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1OC2=CC(O)=C(C\C=C(/C)CCC(O)C(C)=C)C(O)=C2C(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O8/c1-13(2)17(27)9-6-14(3)5-8-16-19(29)12-21-22(23(16)30)24(31)25(32)26(34-21)15-7-10-18(28)20(11-15)33-4/h5,7,10-12,17,25-30,32H,1,6,8-9H2,2-4H3/b14-5+/t17?,25-,26+/m0/s1

> <INCHI_KEY>
IMLYVWIWEAZRNK-ACNRMZSJSA-N

> <FORMULA>
C26H30O8

> <MOLECULAR_WEIGHT>
470.518

> <EXACT_MASS>
470.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.85039095447337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-3,5,7-trihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
4.177682201666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.129993277333643

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.571142759177503

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4430422253529196

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
127.57959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3,5,7-trihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669 -15.400   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   34                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   25                                                       
CONECT   34   24   16                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₈

Average Mass

470.5180 Da

Monoisotopic Mass

470.19407 Da

IUPAC Name

(2R,3R)-3,5,7-trihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-3,5,7-trihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1OC2=CC(O)=C(C\C=C(/C)CCC(O)C(C)=C)C(O)=C2C(=O)[C@@H]1O

InChI Identifier

InChI=1S/C26H30O8/c1-13(2)17(27)9-6-14(3)5-8-16-19(29)12-21-22(23(16)30)24(31)25(32)26(34-21)15-7-10-18(28)20(11-15)33-4/h5,7,10-12,17,25-30,32H,1,6,8-9H2,2-4H3/b14-5+/t17?,25-,26+/m0/s1

InChI Key

IMLYVWIWEAZRNK-ACNRMZSJSA-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
Paulownia tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

6-prenylated flavanone
3p-methoxyflavonoid-skeleton
Flavanone
Flavanonol
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
Chromane
1-benzopyran
Fatty alcohol
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	4.18	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.58 m³·mol⁻¹	ChemAxon
Polarizability	50.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00040495

Chemspider ID

23310150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23626478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Smejkal K, Grycova L, Marek R, Lemiere F, Jankovska D, Forejtnikova H, Vanco J, Suchy V: C-geranyl compounds from Paulownia tomentosa fruits. J Nat Prod. 2007 Aug;70(8):1244-8. doi: 10.1021/np070063w. Epub 2007 Jul 11. [PubMed:17625893 ]
Hanakova Z, Hosek J, Babula P, Dall'Acqua S, Vaclavik J, Smejkal K: C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-alpha Production. J Nat Prod. 2015 Apr 24;78(4):850-63. doi: 10.1021/acs.jnatprod.5b00005. Epub 2015 Mar 4. [PubMed:25735399 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0247730)

MOL for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0247730 ((2r,3r)-3,5,7-trihydroxy-6-[(2e)-6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one)