NP-MRD: Showing NP-Card for (2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate (NP0300362)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 12:43:29 UTC

Updated at

2022-09-10 12:43:29 UTC

NP-MRD ID

NP0300362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Description

3,3'-Di-O-galloylprocyanidin B5, also known as procyanidin b-5 3,3'-di-O-gallate, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 3,3'-Di-O-galloylprocyanidin B5 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,3'-Di-O-galloylprocyanidin B5 has been detected, but not quantified in, green vegetables and tea. (2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate is found in Rumex acetosa. This could make 3,3'-di-O-galloylprocyanidin B5 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217352D          

 64 71  0  0  0  0            999 V2000
   -2.0496    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    2.5981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3351    3.4231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0496    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    5.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    5.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    4.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    4.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    5.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    1.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    2.1856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    1.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -0.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -1.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    0.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165    1.8723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7165    1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -1.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0020    0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0020   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    2.2848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1454    1.8723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1454    1.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0033    1.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    3.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0033    3.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875    1.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    3.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1454    4.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1454    5.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    5.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5743    5.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5743    4.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    3.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    5.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    6.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    3.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165    4.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 53  1  0  0  0  0
  7 53  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
  8 20  1  6  0  0  0
 30 20  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 33  1  0  0  0  0
 32 40  1  0  0  0  0
 33 34  2  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 34 42  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 39  1  0  0  0  0
 38 39  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 46  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 38 51  1  0  0  0  0
 40 52  1  6  0  0  0
 32 53  1  1  0  0  0
 63 52  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
 59 60  1  0  0  0  0
 58 61  1  0  0  0  0
 57 62  1  0  0  0  0
 55 63  1  0  0  0  0
 63 64  2  0  0  0  0
M  END

     RDKit          3D

 98105  0  0  0  0  0  0  0  0999 V2000
   -4.5153    0.3462    2.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258    0.4327    1.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108   -0.2086    0.7910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.9668    0.6614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7362   -0.2109   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.9274   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -2.2847   -0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713   -2.9848   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -2.2884   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -3.0215   -0.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198   -0.9105   -0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758   -0.1560   -1.0325 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1418    0.5350   -2.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -0.2242   -3.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210   -1.6087   -3.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9821    0.3548   -4.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0761    1.7280   -4.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    2.2979   -6.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2014    2.5272   -3.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    1.9085   -2.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    2.6319   -1.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9063    2.0824   -0.1448 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3829    2.3472   -0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    2.7857    1.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659    3.0427    1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1435    2.8601   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4903    3.0985   -0.0682 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5366    2.4271   -1.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2745    2.2367   -2.3677 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    2.1736   -1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918    0.6591    0.1295 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7476    0.1208    0.7928 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7306   -0.3598    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638   -0.3434    2.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9561   -0.8818    2.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1472   -0.9073    1.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2847   -1.4129    2.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4968   -1.4469    1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2659   -1.8984    3.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4351   -2.3996    4.4022 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797   -1.8726    4.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0443   -2.3486    5.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389   -1.3639    3.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062   -0.2437   -0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906    1.1337   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014   -2.9843   -0.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490   -2.3851    0.2413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7291   -2.5625   -0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340   -2.9502   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8919   -3.1264   -1.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4415   -2.9125   -3.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2785   -3.0801   -4.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1233   -2.5228   -3.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836   -2.3111   -4.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2692   -2.3470   -2.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4635    1.2204    1.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2816    1.3488    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4518    2.1058    0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2451    2.2089   -0.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8086    2.7262    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9697    3.4754    2.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0068    2.6063    3.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3456    3.2296    4.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8575    1.8554    3.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -1.0025    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233    0.0414   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5293    0.7651    0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -4.0587   -0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -4.0126   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728   -0.9546   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -2.1931   -4.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8831   -0.2771   -5.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9020    2.4362   -6.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    3.5918   -3.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085    2.6865    0.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    2.9199    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8399    3.3806    1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9262    3.4214    0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2502    2.3851   -2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7233    1.8374   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7668    0.5738    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1406   -0.5266    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3336   -1.8090    2.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4413   -2.7573    5.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -2.3825    6.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399   -1.3669    4.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    1.7534   -0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -2.9375    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4674   -3.1390    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9278   -3.4335   -1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2338   -3.3656   -4.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223   -2.0228   -4.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632   -2.0424   -2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0051    0.8657   -0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1066    2.7567   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2411    3.9300    3.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7447    3.1319    5.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    1.7518    4.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 19 20  1  0
 20 13  2  0
 13 12  1  0
 12 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  2  0
 31 22  1  0
 22 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 12 11  1  0
 11 44  2  0
 44 45  1  0
 44  6  1  0
  6  7  2  0
  7 46  1  0
 46 47  1  0
 47  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 56  1  0
 56 57  2  0
 57 58  1  0
 58 59  1  0
 58 60  2  0
 60 61  1  0
 60 62  1  0
 62 63  1  0
 62 64  2  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 51 52  1  0
 51 53  1  0
 53 54  1  0
 53 55  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 21 20  1  0
 30 23  1  0
  9 11  1  0
 43 35  1  0
  5  6  1  0
 64 56  1  0
 55 48  1  0
 18 73  1  0
 19 74  1  0
 12 70  1  6
 31 81  1  1
 36 82  1  0
 38 83  1  0
 40 84  1  0
 42 85  1  0
 43 86  1  0
 22 75  1  1
 24 76  1  0
 25 77  1  0
 27 78  1  0
 29 79  1  0
 30 80  1  0
 45 87  1  0
 47 88  1  1
  4 65  1  1
  5 66  1  0
  5 67  1  0
 57 94  1  0
 59 95  1  0
 61 96  1  0
 63 97  1  0
 64 98  1  0
 49 89  1  0
 50 90  1  0
 52 91  1  0
 54 92  1  0
 55 93  1  0
  8 68  1  0
 10 69  1  0
 15 71  1  0
 16 72  1  0
M  END


  Mrv0541 02241217352D          

 64 71  0  0  0  0            999 V2000
   -2.0496    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    2.5981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3351    3.4231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0496    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    5.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    5.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    4.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    4.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    5.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    1.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    2.1856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083    1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    1.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -0.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -1.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    0.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165    1.8723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7165    1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -1.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0020    0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0020   -0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    2.2848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1454    1.8723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1454    1.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0033    1.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    3.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0033    3.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875    1.0473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    3.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1454    4.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1454    5.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    5.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5743    5.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5743    4.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    3.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2888    5.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    6.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    3.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165    4.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 53  1  0  0  0  0
  7 53  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
  8 20  1  6  0  0  0
 30 20  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 33  1  0  0  0  0
 32 40  1  0  0  0  0
 33 34  2  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 34 42  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 39  1  0  0  0  0
 38 39  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 46  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 38 51  1  0  0  0  0
 40 52  1  6  0  0  0
 32 53  1  1  0  0  0
 63 52  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
 59 60  1  0  0  0  0
 58 61  1  0  0  0  0
 57 62  1  0  0  0  0
 55 63  1  0  0  0  0
 63 64  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0300362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1

> <INCHI_KEY>
LFBGVECYPPCVDS-QNPRKUGLSA-N

> <FORMULA>
C44H34O20

> <MOLECULAR_WEIGHT>
882.7288

> <EXACT_MASS>
882.164343528

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
82.70938209757075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
6.284952780999999

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.306770124709642

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.765192316743891

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4873751499504

> <JCHEM_POLAR_SURFACE_AREA>
354.28000000000003

> <JCHEM_REFRACTIVITY>
218.0374

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.826   4.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.160   4.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.160   6.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.493   7.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.827   6.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.161   7.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.493   4.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.492   4.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.492   6.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.826   7.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.175  11.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.175   9.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.159   8.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.159   7.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.175   6.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.509   7.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.509   8.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.842   9.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.493   2.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.159   4.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.509   2.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.175   1.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.175   0.230   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.509  -0.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.842   0.230   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.842   1.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.176   2.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.176  -0.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.509  -2.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.159   2.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.492   1.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -10.671   3.495   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.671   1.955   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -12.004   1.185   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.004  -0.355   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.671  -1.125   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.671  -2.665   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -9.337   1.185   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.337  -0.355   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -12.004   4.265   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -13.338   3.495   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -13.338   1.955   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -18.673   3.495   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -17.339   4.265   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -16.006   3.495   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -14.672   4.265   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -14.672   5.805   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -16.006   6.575   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -17.339   5.805   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -18.673   6.575   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -8.003   1.955   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -12.004   5.805   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -7.827   4.850   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -14.672   7.345   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -13.338   8.115   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -13.338   9.655   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -14.672  10.425   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -16.005   9.655   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -16.005   8.115   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0     -17.339   7.345   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0     -17.339  10.425   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -14.672  11.965   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0     -12.004   7.345   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -10.671   8.115   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   53                                                  
CONECT    6    5                                                            
CONECT    7    2   53   19                                                  
CONECT    8    1    9   20                                                  
CONECT    9    8   10   14                                                  
CONECT   10    3    9                                                       
CONECT   11   12                                                            
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17                                                            
CONECT   19    7                                                            
CONECT   20    8   30                                                       
CONECT   21   22   26                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   20   22   31                                                  
CONECT   31   30                                                            
CONECT   32   33   40   53                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36                                                            
CONECT   38   33   39   51                                                  
CONECT   39   36   38                                                       
CONECT   40   32   41   52                                                  
CONECT   41   40   42   46                                                  
CONECT   42   34   41                                                       
CONECT   43   44                                                            
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   41   45   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   44   48   50                                                  
CONECT   50   49                                                            
CONECT   51   38                                                            
CONECT   52   40   63                                                       
CONECT   53    5    7   32                                                  
CONECT   54   55   59                                                       
CONECT   55   54   56   63                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59   61                                                  
CONECT   59   58   54   60                                                  
CONECT   60   59                                                            
CONECT   61   58                                                            
CONECT   62   57                                                            
CONECT   63   52   55   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

View in JSmol

Synonyms

Value	Source
3-O-Galloylepicatechin-(4beta->6)-epicatechin-3-O-gallate	HMDB
Procyanidin b-5 3,3'-di-O-gallate	HMDB
Procyanidin b5 3,3'-di-O-gallate	HMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid	Generator
Procyanidin b5 3,3'-digallic acid	Generator

Chemical Formula

C₄₄H₃₄O₂₀

Average Mass

882.7288 Da

Monoisotopic Mass

882.16434 Da

IUPAC Name

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

InChI Identifier

InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1

InChI Key

LFBGVECYPPCVDS-QNPRKUGLSA-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
Rumex acetosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin gallate
Epigallocatechin
Catechin
Hydroxyflavonoid
Flavan-3-ol
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Organic oxygen compound
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	3.91	ALOGPS
logP	6.28	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	354.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	218.04 m³·mol⁻¹	ChemAxon
Polarizability	82.71 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039299

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018845

KNApSAcK ID

C00009207

Chemspider ID

2343127

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086518

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate (NP0300362)

MOL for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0300362 ((2r,3r,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)