NP-MRD: Showing NP-Card for 6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione (NP0201697)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 20:47:35 UTC

Updated at

2022-09-04 20:47:35 UTC

NP-MRD ID

NP0201697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

Description

TMEG 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. 6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione is found in Aphananthe aspera, Camptotheca acuminata, Cleidion brevipetiolatum, Dipentodon sinicus, Euphorbia sessiliflora, Nyssa sylvatica, Phyllagathis rotundifolia and Psidium guajava. 6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione was first documented in 2018 (PMID: 29473409). Based on a literature review a small amount of articles have been published on TMEG (PMID: 35860136) (PMID: 32861995) (PMID: 31379766) (PMID: 30691532).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222472D          

 36 40  0  0  1  0            999 V2000
    5.9664   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4586   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.6039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6961    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.3184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8711    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2211    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 31 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9 36  1  0  0  0  0
 27 36  2  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    7.6460    2.5397   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2520    1.2055   -0.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9049    0.8942   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469    1.8728   -0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163    1.5777   -0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326    2.4940   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730    3.6902    0.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433    2.1710    0.0160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    0.9274   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260    0.6270   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803    1.6881    0.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    1.9853    1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -0.6655   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682   -1.0805   -0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3157   -0.5557   -0.1389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9128   -0.8902    1.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0615   -0.0716    1.1741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6263   -0.0596    2.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0045   -1.3110    3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1356   -0.5760    0.2304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7388    0.4239   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4763   -1.5799   -0.6934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0935   -2.6869    0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2356   -0.9554   -1.2828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5276    0.1599   -2.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863   -1.6205   -0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5123   -1.3278   -0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -2.2637   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -3.4530   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.9682   -1.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -0.7301   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152   -0.4144   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4913   -1.3571   -1.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906   -2.0645   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462    0.2618   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -0.0227   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4450    2.8212    0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0696    3.2735   -1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126    2.7038   -0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.8904   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    1.0217    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638    2.3969    1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    2.6238    1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785    0.5506   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7934    0.9599    0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8984    0.4302    3.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5254    0.5886    2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1060   -1.2728    3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9299   -1.1225    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2781    1.2769   -0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1622   -1.9138   -1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7593   -3.0138    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7698   -1.7323   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2454    0.1025   -2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079   -2.6668   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2761   -1.3965    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0480   -2.5209   -0.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3704   -2.8652    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 33  1  0
 33 34  1  0
 32 31  1  0
 31 35  2  0
 35  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  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 36  2  0
  4  3  1  0
 36  9  1  0
 30 31  1  0
 36 35  1  0
 24 15  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 34 56  1  0
 34 57  1  0
 34 58  1  0
  4 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 15 44  1  1
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  1
 21 50  1  0
 22 51  1  6
 23 52  1  0
 24 53  1  6
 25 54  1  0
 26 55  1  0
M  END


  Mrv1652309042222472D          

 36 40  0  0  1  0            999 V2000
    5.9664   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4586   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.6039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6961    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.3184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8711    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2211    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 31 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9 36  1  0  0  0  0
 27 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0201697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C3C(=C1)C(=O)OC1=C(OC)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=CC(C(=O)O2)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O13/c1-30-9-4-7-12-13-8(22(29)35-19(12)17(9)31-2)5-10(18(32-3)20(13)36-21(7)28)33-23-16(27)15(26)14(25)11(6-24)34-23/h4-5,11,14-16,23-27H,6H2,1-3H3/t11-,14-,15+,16-,23-/m1/s1

> <INCHI_KEY>
RKFCDGOVCBYSEW-AUUKWEANSA-N

> <FORMULA>
C23H22O13

> <MOLECULAR_WEIGHT>
506.416

> <EXACT_MASS>
506.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
48.07625000398446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,13,14-trimethoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <JCHEM_LOGP>
-0.8144635073333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19604286934388

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200012612886663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549535993

> <JCHEM_POLAR_SURFACE_AREA>
179.67

> <JCHEM_REFRACTIVITY>
116.19889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7,13,14-trimethoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.723  -0.206   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.493   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.033   1.127   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.803  -0.206   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.723   2.461   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.493   3.795   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.183   2.461   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.413   3.795   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.413   1.127   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31    3   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   31    5   36                                                  
CONECT   36   35    9   27                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₁₃

Average Mass

506.4160 Da

Monoisotopic Mass

506.10604 Da

IUPAC Name

7,13,14-trimethoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

Traditional Name

7,13,14-trimethoxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C3C(=C1)C(=O)OC1=C(OC)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=CC(C(=O)O2)=C31

InChI Identifier

InChI=1S/C23H22O13/c1-30-9-4-7-12-13-8(22(29)35-19(12)17(9)31-2)5-10(18(32-3)20(13)36-21(7)28)33-23-16(27)15(26)14(25)11(6-24)34-23/h4-5,11,14-16,23-27H,6H2,1-3H3/t11-,14-,15+,16-,23-/m1/s1

InChI Key

RKFCDGOVCBYSEW-AUUKWEANSA-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
Aphananthe aspera	LOTUS Database	35616633
Camptotheca acuminata	LOTUS Database	35616633
Cleidion brevipetiolatum	LOTUS Database	35616633
Dipentodon sinicus	LOTUS Database	35616633
Euphorbia sessiliflora	LOTUS Database	35616633
Nyssa sylvatica	LOTUS Database	35616633
Phyllagathis rotundifolia	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633

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
Ellagic_acid
Phenolic glycoside
Hexose monosaccharide
Isocoumarin
Coumarin
O-glycosyl compound
Glycosyl compound
Benzopyran
2-benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Monosaccharide
Benzenoid
Oxane
Pyran
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.81	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	179.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.2 m³·mol⁻¹	ChemAxon
Polarizability	48.08 Å³	ChemAxon
Number of Rings	5	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

23340064

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44567156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kbirou A, Jandou I, Sayah M, Benhadda H, Moataz A, Dakir M, Debbagh A, Aboutaieb R: Forensic aspects of trauma to the male external genitalia (TMEG), analysis of a series of 84 cases. Ann Med Surg (Lond). 2022 Jun 6;79:103916. doi: 10.1016/j.amsu.2022.103916. eCollection 2022 Jul. [PubMed:35860136 ]
Ramirez GA, McKay LJ, Fields MW, Buckley A, Mortera C, Hensen C, Ravelo AC, Teske AP: The Guaymas Basin Subseafloor Sedimentary Archaeome Reflects Complex Environmental Histories. iScience. 2020 Aug 15;23(9):101459. doi: 10.1016/j.isci.2020.101459. eCollection 2020 Sep 25. [PubMed:32861995 ]
Gavrilov SN, Korzhenkov AA, Kublanov IV, Bargiela R, Zamana LV, Popova AA, Toshchakov SV, Golyshin PN, Golyshina OV: Microbial Communities of Polymetallic Deposits' Acidic Ecosystems of Continental Climatic Zone With High Temperature Contrasts. Front Microbiol. 2019 Jul 17;10:1573. doi: 10.3389/fmicb.2019.01573. eCollection 2019. [PubMed:31379766 ]
Korzhenkov AA, Toshchakov SV, Bargiela R, Gibbard H, Ferrer M, Teplyuk AV, Jones DL, Kublanov IV, Golyshin PN, Golyshina OV: Archaea dominate the microbial community in an ecosystem with low-to-moderate temperature and extreme acidity. Microbiome. 2019 Jan 28;7(1):11. doi: 10.1186/s40168-019-0623-8. [PubMed:30691532 ]
Chun J, Kishore RA, Kumar P, Kang MG, Kang HB, Sanghadasa M, Priya S: Self-Powered Temperature-Mapping Sensors Based on Thermo-Magneto-Electric Generator. ACS Appl Mater Interfaces. 2018 Apr 4;10(13):10796-10803. doi: 10.1021/acsami.7b17686. Epub 2018 Mar 26. [PubMed:29473409 ]
LOTUS database [Link]

Showing NP-Card for 6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione (NP0201697)

MOL for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D MOL for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D SDF for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D-SDF for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

PDB for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D PDB for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

SMILES for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

INCHI for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

Structure for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D Structure for NP0201697 (6,7,14-trimethoxy-13-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)