NP-MRD: Showing NP-Card for 5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0238532)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 21:56:31 UTC

Updated at

2022-09-06 21:56:31 UTC

NP-MRD ID

NP0238532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Description

Prodelphinidin A1 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''. Prodelphinidin A1 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, prodelphinidin A1 has been detected, but not quantified in, fruits. 5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol is found in Phyllanthus emblica. This could make prodelphinidin A1 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211162D          

 44 50  0  0  0  0            999 V2000
   -1.1301    2.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    2.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011    3.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    3.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9128    4.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7391    1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905    1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9169    0.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -0.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599   -0.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -1.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1149   -2.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -3.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -4.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -1.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5795   -0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108    0.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426   -3.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537   -3.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    2.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    3.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3398    3.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    3.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572    2.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    2.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350    1.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.8922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3720   -0.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -1.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -1.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -1.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -4.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -2.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 29  2  0  0  0  0
  2  3  2  0  0  0  0
  2 34  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 30  2  0  0  0  0
  6  7  1  0  0  0  0
  6 33  1  0  0  0  0
  7  8  1  0  0  0  0
  7 37  2  0  0  0  0
  8  9  2  0  0  0  0
  8 35  1  0  0  0  0
  9 10  1  0  0  0  0
  9 39  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 12  1  0  0  0  0
 11 41  1  0  0  0  0
 12 13  1  0  0  0  0
 12 40  1  0  0  0  0
 12 44  1  0  0  0  0
 13 14  1  0  0  0  0
 13 25  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 43  1  0  0  0  0
 16 17  1  0  0  0  0
 16 26  2  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 42  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 44  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

 68 74  0  0  0  0  0  0  0  0999 V2000
   -1.3069    4.2402   -4.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    3.3506   -3.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    3.0977   -2.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2510    2.2125   -1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495    2.0307   -1.1836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    1.5816   -1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0723    1.8556   -1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.7247   -2.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    1.2763   -1.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533    0.2095   -0.1551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3368   -0.1383    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -1.3917    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0966   -1.7455    0.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6109   -3.0423    0.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7484   -0.8310    1.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9380   -1.2109    2.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2087    0.4276    1.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8937    1.3352    2.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0157    0.7695    1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -0.9045   -0.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -1.4984   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265   -2.8329   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243   -3.3750   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2443   -4.7309   -1.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884   -2.6254   -0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116   -1.3060   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4324   -0.7480   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    0.6543    0.0789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0166    0.6669    0.8160 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9633   -0.1835    1.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466   -0.5320    0.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1699   -0.9287    0.0122 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1938    0.0397    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    0.4051   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1913    1.3133   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1815    1.6495   -1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2028    1.9149    1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818    2.8579    1.4088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220    1.5827    1.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476    2.2001    3.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302    0.6669    1.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -2.3212    0.5179 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6468   -2.8099    0.3277 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176   -3.2485   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528    5.2144   -4.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9754    3.5929   -3.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286    2.5040   -1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369    2.9279   -3.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4140   -2.1211   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -3.7033    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3258   -2.1264    2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7587    1.0871    3.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    1.7763    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -3.4162   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -5.1419   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0622    1.0465    0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    1.7097    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174    0.2832    2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003   -1.0119   -1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182   -0.0553   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1555    1.1811   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8897    3.0707    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534    2.8707    3.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4576    0.4049    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -2.3573    1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013   -2.5686    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2278   -4.1205    0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446   -3.7055   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
 43 42  1  0
 42 44  1  0
 44 25  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  8  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6 28  1  0
 28 29  1  0
 29 30  1  0
 28 27  1  0
 27 26  2  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  2  0
 10 11  1  1
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 32 42  1  0
 41 33  1  0
 19 11  1  0
 26 25  1  0
 27 21  1  0
 29 10  1  0
  6  7  1  0
 43 66  1  0
 42 65  1  1
 44 67  1  0
 44 68  1  0
 24 55  1  0
 22 54  1  0
  8 48  1  0
  1 45  1  0
  3 46  1  0
  5 47  1  0
 28 56  1  1
 29 57  1  1
 30 58  1  0
 32 59  1  6
 34 60  1  0
 36 61  1  0
 38 62  1  0
 40 63  1  0
 41 64  1  0
 12 49  1  0
 14 50  1  0
 16 51  1  0
 18 52  1  0
 19 53  1  0
M  END


  Mrv0541 02241211162D          

 44 50  0  0  0  0            999 V2000
   -1.1301    2.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    2.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011    3.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    3.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9128    4.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7391    1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905    1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9169    0.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -0.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599   -0.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159   -1.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1149   -2.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -3.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -4.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -1.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5795   -0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108    0.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426   -3.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537   -3.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    2.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    3.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3398    3.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    3.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572    2.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    2.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350    1.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.8922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3720   -0.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -1.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -1.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -1.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -4.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -2.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 29  2  0  0  0  0
  2  3  2  0  0  0  0
  2 34  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 30  2  0  0  0  0
  6  7  1  0  0  0  0
  6 33  1  0  0  0  0
  7  8  1  0  0  0  0
  7 37  2  0  0  0  0
  8  9  2  0  0  0  0
  8 35  1  0  0  0  0
  9 10  1  0  0  0  0
  9 39  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 12  1  0  0  0  0
 11 41  1  0  0  0  0
 12 13  1  0  0  0  0
 12 40  1  0  0  0  0
 12 44  1  0  0  0  0
 13 14  1  0  0  0  0
 13 25  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 43  1  0  0  0  0
 16 17  1  0  0  0  0
 16 26  2  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 42  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 44  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O)C=C3OC4(OC5=CC(O)=CC(O)=C5C(C4O)C3=C2OC1C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O14/c31-11-5-14(33)22-20(6-11)43-30(10-3-17(36)26(40)18(37)4-10)29(41)24(22)23-21(44-30)8-13(32)12-7-19(38)27(42-28(12)23)9-1-15(34)25(39)16(35)2-9/h1-6,8,19,24,27,29,31-41H,7H2

> <INCHI_KEY>
SJDDGZBVGOKCKT-UHFFFAOYSA-N

> <FORMULA>
C30H24O14

> <MOLECULAR_WEIGHT>
608.5032

> <EXACT_MASS>
608.116605476

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
58.56424809035298

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.9834014533333333

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.927848058640523

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.418163375582226

> <JCHEM_PKA_STRONGEST_BASIC>
-5.217530837356386

> <JCHEM_POLAR_SURFACE_AREA>
250.21999999999994

> <JCHEM_REFRACTIVITY>
148.15810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <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      -2.110   3.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.706   4.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.562   6.251   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.835   7.119   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.704   8.604   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.246   3.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.969   2.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.712   1.401   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.286  -0.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.118  -0.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.232  -1.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.150  -3.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.081  -4.621   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.224  -5.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.163  -7.178   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.659  -7.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.450  -8.430   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.352  -1.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.498  -2.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.223  -3.559   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.817  -2.931   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.670  -1.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.948  -0.433   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.820   1.055   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.600  -4.460   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.373  -5.874   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.887  -5.705   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.642   4.208   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.382   4.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.241   6.490   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.368   7.337   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.115   6.018   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.973   4.381   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.567   3.749   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.439   2.268   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.630   1.665   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.229   1.036   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.952  -0.441   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.561  -0.919   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.263  -2.543   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.572  -2.440   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.887  -3.179   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.283  -8.604   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.405  -3.954   0.000  0.00  0.00           O+0
CONECT    1    2   29                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4                                                            
CONECT    6    7   33                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   41                                                  
CONECT   12   11   13   40   44                                             
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   43                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16                                                            
CONECT   18   19   23                                                       
CONECT   19   18   20   42                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   44                                                  
CONECT   22   10   21   23                                                  
CONECT   23   18   22   24                                                  
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   16   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29    1   28   30                                                  
CONECT   30    4   29   31                                                  
CONECT   31   30                                                            
CONECT   32   33                                                            
CONECT   33    6   32   34                                                  
CONECT   34    2   33   35                                                  
CONECT   35    8   34                                                       
CONECT   36   37                                                            
CONECT   37    7   36   38                                                  
CONECT   38   37   39                                                       
CONECT   39    9   38   40                                                  
CONECT   40   12   39                                                       
CONECT   41   11                                                            
CONECT   42   19                                                            
CONECT   43   15                                                            
CONECT   44   12   21                                                       
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Value	Source
Epigallocatechin-(2b->7,4b->8)-gallocatechin	HMDB

Chemical Formula

C₃₀H₂₄O₁₄

Average Mass

608.5032 Da

Monoisotopic Mass

608.11661 Da

IUPAC Name

5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

OC1CC2=C(O)C=C3OC4(OC5=CC(O)=CC(O)=C5C(C4O)C3=C2OC1C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H24O14/c31-11-5-14(33)22-20(6-11)43-30(10-3-17(36)26(40)18(37)4-10)29(41)24(22)23-21(44-30)8-13(32)12-7-19(38)27(42-28(12)23)9-1-15(34)25(39)16(35)2-9/h1-6,8,19,24,27,29,31-41H,7H2

InChI Key

SJDDGZBVGOKCKT-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
Phyllanthus emblica	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

Not Available

Substituents

Not Available

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	2.25	ALOGPS
logP	2.98	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	250.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	148.16 m³·mol⁻¹	ChemAxon
Polarizability	58.56 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036336

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015207

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

14521015

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0238532)

MOL for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D MOL for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D SDF for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D-SDF for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

PDB for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D PDB for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

SMILES for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

INCHI for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

Structure for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D Structure for NP0238532 (5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)