NP-MRD: Showing NP-Card for (-)-Picroroside B (NP0074155)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 19:19:13 UTC

Updated at

2022-04-28 19:19:13 UTC

NP-MRD ID

NP0074155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Picroroside B

Description

(1R,4S,5R,6S,7R,8S,9S)-4,6-dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(3-phenylprop-2-enoyl)oxy]methyl}oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0⁴,⁸]Undecan-5-yl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (-)-Picroroside B is found in Neopicrorhiza scrophulariiflora . Based on a literature review very few articles have been published on (1R,4S,5R,6S,7R,8S,9S)-4,6-dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(3-phenylprop-2-enoyl)oxy]methyl}oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0⁴,⁸]Undecan-5-yl 4-hydroxy-3-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221192D          

 47 52  0  0  1  0            999 V2000
    2.2791    0.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144    1.1414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4043    1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.8389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7526   -0.1370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5777   -0.4623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7264   -1.2738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035   -1.5508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1319   -1.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -1.2933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0577   -2.1048    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4292   -2.6393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -2.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0237   -2.8968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779   -3.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -2.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -1.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9430   -0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944    0.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7201   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1257   -0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5313   -0.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6799   -1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0515   -1.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2744   -1.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392    0.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0182   -0.1869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4789    0.5045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2725    0.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630   -0.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502   -0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0438    0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2454    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6533    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0390    1.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6359   -0.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4295   -0.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 12 17  1  1  0  0  0
 11 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  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
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 39 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  0  0  0  0
 31 45  1  6  0  0  0
 30 46  1  6  0  0  0
  2 46  1  1  0  0  0
  5 47  1  6  0  0  0
M  END

     RDKit          3D

 83 88  0  0  0  0  0  0  0  0999 V2000
   10.4734    2.8296    1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5090    1.5173    0.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4307    0.7104    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1176    1.1406    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0506    0.3142    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849    0.7953    0.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801    1.9606    1.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5956    0.0015    0.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.4108    0.5316 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6762   -0.4677    1.6402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0315    0.3000    2.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -1.3948    0.9270 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5958   -2.4204    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398   -2.6915   -1.1677 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4184   -1.7934   -2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1238   -0.7052   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4052    0.1628   -0.6902 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0450    1.4030   -1.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -0.4848   -0.1464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3741   -1.2187   -1.1829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9947   -1.0568   -1.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5189   -0.5154   -2.2970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0315    0.7158   -2.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090    0.7928   -1.5555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2869    0.5718   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5991    0.6434    0.4836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501    0.4934    1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572    0.2714    2.6430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3482    0.5837    2.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3327    0.8157    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7190    0.9168    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6689    1.1634    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0120    1.2758    1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4555    1.1393    2.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5469    0.8969    3.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1965    0.7879    3.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2857   -0.1815   -2.1248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6464    0.2424   -3.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429   -1.5761   -2.2352 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5456   -2.1894   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307   -1.4689   -2.9940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7543   -0.9056   -4.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6328   -2.6019   -1.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3285   -0.9513   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6328   -1.3889   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6967   -0.5606    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0188   -1.0035   -0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3175    3.4518    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5641    2.7675    2.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5509    3.3420    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9107    2.1354    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1974    1.4529    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -1.0683    2.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229    0.7625    3.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -1.8476    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -2.1616    0.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -3.3651    0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541   -3.7355   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684   -0.9669   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3025   -0.0567   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.9733   -0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    0.3119    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7343   -0.8703   -2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6389   -0.3673   -2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    1.8365   -1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8121   -0.3665    0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    1.4057    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871    0.4604    3.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0664    0.9379    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3552    1.2772   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7715    1.4662    0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5201    1.2256    2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8737    0.7877    4.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5006    0.5961    3.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2361   -0.2272   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2851   -0.4418   -3.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813   -2.1660   -2.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2627   -2.7834   -0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -2.4479   -3.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854   -0.1427   -4.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5075   -1.6029   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8666   -2.3838   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8001   -0.3991    0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 46  2  0
 46 47  1  0
 46 45  1  0
 45 44  2  0
 44  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 43  1  0
 43 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 24 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  6
 17 16  1  0
 16 15  1  0
  4  3  1  0
 17  9  1  0
 19 12  1  0
 15 14  1  0
 41 22  1  0
 36 31  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
 47 83  1  0
 45 82  1  0
 44 81  1  0
  4 51  1  0
  9 52  1  1
 10 53  1  1
 11 54  1  0
 12 55  1  1
 13 56  1  0
 13 57  1  0
 14 58  1  6
 20 63  1  6
 22 64  1  6
 24 65  1  1
 25 66  1  0
 25 67  1  0
 29 68  1  0
 30 69  1  0
 32 70  1  0
 33 71  1  0
 34 72  1  0
 35 73  1  0
 36 74  1  0
 37 75  1  1
 38 76  1  0
 39 77  1  6
 40 78  1  0
 41 79  1  6
 42 80  1  0
 19 62  1  1
 18 61  1  0
 16 59  1  0
 16 60  1  0
M  END


  Mrv1652304282221192D          

 47 52  0  0  1  0            999 V2000
    2.2791    0.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144    1.1414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4043    1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.8389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7526   -0.1370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5777   -0.4623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7264   -1.2738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035   -1.5508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1319   -1.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -1.2933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0577   -2.1048    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4292   -2.6393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -2.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0237   -2.8968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779   -3.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -2.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -1.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9430   -0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944    0.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7201   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1257   -0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5313   -0.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6799   -1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0515   -1.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2744   -1.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392    0.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0182   -0.1869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4789    0.5045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2725    0.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630   -0.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502   -0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0438    0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2454    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6533    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0390    1.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6359   -0.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4295   -0.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 12 17  1  1  0  0  0
 11 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  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
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 39 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  0  0  0  0
 31 45  1  6  0  0  0
 30 46  1  6  0  0  0
  2 46  1  1  0  0  0
  5 47  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)O[C@@H]1[C@@H](O)[C@@H]2C[C@H]3O[C@@H](O[C@@H]4O[C@H](COC(=O)\C=C\C5=CC=CC=C5)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2[C@]1(O)CO3

> <INCHI_IDENTIFIER>
InChI=1S/C32H36O15/c1-41-19-11-16(8-9-18(19)33)29(39)46-28-24(35)17-12-22-43-14-32(28,40)23(17)30(45-22)47-31-27(38)26(37)25(36)20(44-31)13-42-21(34)10-7-15-5-3-2-4-6-15/h2-11,17,20,22-28,30-31,33,35-38,40H,12-14H2,1H3/b10-7+/t17-,20-,22-,23-,24+,25-,26+,27-,28-,30+,31+,32-/m1/s1

> <INCHI_KEY>
IKXQFQNHWKQJOI-MNMDYHDTSA-N

> <FORMULA>
C32H36O15

> <MOLECULAR_WEIGHT>
660.625

> <EXACT_MASS>
660.205420459

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
65.31841356402028

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,5R,6S,7R,8S,9S)-4,6-dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0^{4,8}]undecan-5-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.0312459169999997

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.05272415920456

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.985960181521884

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3229473505299545

> <JCHEM_POLAR_SURFACE_AREA>
220.12999999999997

> <JCHEM_REFRACTIVITY>
156.07250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,6S,7R,8S,9S)-4,6-dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0^{4,8}]undecan-5-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       4.254   0.328   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.760   2.131   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.621   3.327   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.021   3.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.469   1.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.405  -0.256   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.945  -0.863   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.223  -2.378   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.673  -2.895   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.846  -1.897   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.297  -2.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.574  -3.929   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.401  -4.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.951  -4.410   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.778  -5.407   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.679  -6.441   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.025  -4.446   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.470  -1.416   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.921  -1.934   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.094  -0.936   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.816   0.579   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.544  -1.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.717  -0.455   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.168  -0.972   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.341   0.025   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.792  -0.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.069  -2.007   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.896  -3.004   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.445  -2.487   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.567   0.652   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.034  -0.349   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.894   0.942   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.375   1.363   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.481   0.290   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.104  -1.203   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.962   0.711   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.067  -0.362   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.548   0.059   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.925   1.553   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.820   2.625   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.338   2.204   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -9.406   1.973   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -8.654  -1.013   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -10.135  -0.592   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -0.358  -1.854   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       3.462   1.075   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -0.666   2.606   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   46                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   32   47                                             
CONECT    6    5    7   30                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   12                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30    6   31   46                                                  
CONECT   31   30   32   45                                                  
CONECT   32   31    5   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   39                                                            
CONECT   43   38   44                                                       
CONECT   44   43                                                            
CONECT   45   31                                                            
CONECT   46   30    2                                                       
CONECT   47    5                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
(1R,4S,5R,6S,7R,8S,9S)-4,6-Dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(3-phenylprop-2-enoyl)oxy]methyl}oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0,]undecan-5-yl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₃₂H₃₆O₁₅

Average Mass

660.6250 Da

Monoisotopic Mass

660.20542 Da

IUPAC Name

(1R,4S,5R,6S,7R,8S,9S)-4,6-dihydroxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0^{4,8}]undecan-5-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)O[C@@H]1[C@@H](O)[C@@H]2C[C@H]3O[C@@H](O[C@@H]4O[C@H](COC(=O)\C=C\C5=CC=CC=C5)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2[C@]1(O)CO3

InChI Identifier

InChI=1S/C32H36O15/c1-41-19-11-16(8-9-18(19)33)29(39)46-28-24(35)17-12-22-43-14-32(28,40)23(17)30(45-22)47-31-27(38)26(37)25(36)20(44-31)13-42-21(34)10-7-15-5-3-2-4-6-15/h2-11,17,20,22-28,30-31,33,35-38,40H,12-14H2,1H3/b10-7+/t17-,20-,22-,23-,24+,25-,26+,27-,28-,30+,31+,32-/m1/s1

InChI Key

IKXQFQNHWKQJOI-MNMDYHDTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Neopicrorhiza scrophulariiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Cinnamic acid ester
Cinnamic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-glycosyl compound
M-methoxybenzoic acid or derivatives
Glycosyl compound
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxepane
Fatty acid ester
Dioxepane
Alkyl aryl ether
1,3-dioxepane
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.92	ALOGPS
logP	1.03	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	220.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	156.07 m³·mol⁻¹	ChemAxon
Polarizability	65.32 Å³	ChemAxon
Number of Rings	6	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

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

162943919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Picroroside B (NP0074155)

MOL for NP0074155 ((-)-Picroroside B)

3D MOL for NP0074155 ((-)-Picroroside B)

3D SDF for NP0074155 ((-)-Picroroside B)

3D-SDF for NP0074155 ((-)-Picroroside B)

PDB for NP0074155 ((-)-Picroroside B)

3D PDB for NP0074155 ((-)-Picroroside B)

SMILES for NP0074155 ((-)-Picroroside B)

INCHI for NP0074155 ((-)-Picroroside B)

Structure for NP0074155 ((-)-Picroroside B)

3D Structure for NP0074155 ((-)-Picroroside B)