NP-MRD: Showing NP-Card for methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate (NP0152335)

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Record Information

Version

2.0

Created at

2022-09-02 08:47:53 UTC

Updated at

2022-09-02 08:47:53 UTC

NP-MRD ID

NP0152335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate

Description

Methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate is found in Smilax china. Methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508102D          

 35 38  0  0  0  0            999 V2000
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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  2  0  0  0  0
  3  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
  6 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  2  0  0  0  0
 19 20  1  0  0  0  0
 19 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
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 21 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 35  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    1.2314    4.4648   -1.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    3.6022   -0.8441 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    2.3196   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362    1.9808   -0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.3776    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952    0.0932    0.4622 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4662   -0.9011    1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846   -1.7212    2.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -2.6595    2.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602   -2.8371    2.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956   -3.7904    3.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742   -2.0413    1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -2.2343    1.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229   -1.0860    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.4256   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642   -0.6473   -1.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -0.3585   -1.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024   -1.1441   -3.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0435   -1.4434   -3.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397   -1.9446   -4.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -1.2327   -1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193   -0.7429   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823   -0.5435    0.2622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -0.8877    0.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1965    0.3215    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903    0.6237   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0312    1.7507    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942    2.5923    1.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4770    3.7390    1.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929    2.3171    1.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551    3.1759    2.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622    1.1898    1.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8063   -1.8249   -0.6884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3789   -3.1245   -0.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -1.5687   -2.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006    5.2338   -2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    4.9769   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804    3.8851   -2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6053    1.8088    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    1.2155   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8259    0.3858    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -1.6025    2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8034   -3.2733    3.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4136   -3.9058    3.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4246   -1.6944    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.4861    0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -0.4891   -2.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.2864   -3.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577   -2.0896   -5.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -1.4337    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5491   -0.0496   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.9324   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2712    3.9127    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    3.9771    3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795    0.9464    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9016   -1.8897   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940   -3.1012    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312   -0.8340   -2.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979   -2.5278   -2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
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 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
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 33 34  1  0
 33 35  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 14  7  1  0
 22 15  1  0
 32 25  1  0
 35 21  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  8 42  1  0
  9 43  1  0
 11 44  1  0
 13 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 20 49  1  0
 24 50  1  1
 33 56  1  6
 34 57  1  0
 35 58  1  0
 35 59  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
 32 55  1  0
M  END


  Mrv1533004161508102D          

 35 38  0  0  0  0            999 V2000
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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  2  0  0  0  0
  3  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
  6 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  2  0  0  0  0
 19 20  1  0  0  0  0
 19 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
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 21 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(C1=CC=C(O)C(O)=C1)C1=C(O)C=C(O)C2=C1OC(C(O)C2)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O10/c1-34-22(33)9-13(11-2-4-15(26)18(29)6-11)23-20(31)10-17(28)14-8-21(32)24(35-25(14)23)12-3-5-16(27)19(30)7-12/h2-7,10,13,21,24,26-32H,8-9H2,1H3

> <INCHI_KEY>
QNAHIWNQXWCADO-UHFFFAOYSA-N

> <FORMULA>
C25H24O10

> <MOLECULAR_WEIGHT>
484.457

> <EXACT_MASS>
484.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.363432716997956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.8370104513333336

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.256356773763367

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.781949941134485

> <JCHEM_PKA_STRONGEST_BASIC>
-3.291160719303372

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
123.28280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    6   16   27                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   15   21                                                  
CONECT   28   25   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoic acid	Generator

Chemical Formula

C₂₅H₂₄O₁₀

Average Mass

484.4570 Da

Monoisotopic Mass

484.13695 Da

IUPAC Name

methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate

Traditional Name

methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC(C1=CC=C(O)C(O)=C1)C1=C(O)C=C(O)C2=C1OC(C(O)C2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C25H24O10/c1-34-22(33)9-13(11-2-4-15(26)18(29)6-11)23-20(31)10-17(28)14-8-21(32)24(35-25(14)23)12-3-5-16(27)19(30)7-12/h2-7,10,13,21,24,26-32H,8-9H2,1H3

InChI Key

QNAHIWNQXWCADO-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
Smilax china	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Linear 1,7-diphenylheptane skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Methyl ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Polyol
Ether
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.06	ALOGPS
logP	2.84	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.28 m³·mol⁻¹	ChemAxon
Polarizability	47.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73086892

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate (NP0152335)

MOL for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

3D MOL for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

3D SDF for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

3D-SDF for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

PDB for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

3D PDB for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

SMILES for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

INCHI for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

Structure for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)

3D Structure for NP0152335 (methyl 3-(3,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]propanoate)