NP-MRD: Showing NP-Card for 2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid (NP0304476)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 19:35:51 UTC

Updated at

2022-09-10 19:35:51 UTC

NP-MRD ID

NP0304476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid

Description

Mallotinic acid, also known as mallotinate, 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. 2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid is found in Cunonia macrophylla, Lotus corniculatus, Mallotus japonicus and Mallotus repandus. 2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid was first documented in 2005 (PMID: 15652581). Based on a literature review a small amount of articles have been published on Mallotinic acid (PMID: 32517934) (PMID: 25454458) (PMID: 26054265).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102221352D          

 57 62  0  0  1  0            999 V2000
    1.5077    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -0.6691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5878   -0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -0.2014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9381    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    0.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932   -2.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -3.9432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -4.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -5.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -5.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -4.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -6.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482   -6.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -7.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -5.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -5.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -4.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -4.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9650   -3.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -3.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684   -3.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279   -1.6046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3178   -1.4486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7777   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -0.9809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2318   -1.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    1.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    2.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  0  0  0  0
 21 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 44 43  1  6  0  0  0
 44 45  1  0  0  0  0
  4 45  1  0  0  0  0
 45 46  1  1  0  0  0
 44 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  1  0  0  0
  2 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 49 57  1  0  0  0  0
M  END


  Mrv1652309102221352D          

 57 62  0  0  1  0            999 V2000
    1.5077    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -0.6691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5878   -0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -0.2014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9381    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    0.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932   -2.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -3.9432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -4.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -5.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -5.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -4.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -6.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482   -6.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -7.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -5.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -5.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -4.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -4.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9650   -3.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -3.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9684   -3.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279   -1.6046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3178   -1.4486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7777   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -0.9809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2318   -1.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329   -0.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    1.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    2.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  0  0  0  0
 21 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 44 43  1  6  0  0  0
 44 45  1  0  0  0  0
  4 45  1  0  0  0  0
 45 46  1  1  0  0  0
 44 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  1  0  0  0
  2 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 49 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(OC4=C(C=C(O)C(O)=C4O)C(O)=O)C(O)=C3O)C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C34H26O23/c35-11-1-7(2-12(36)19(11)39)31(50)57-34-27(47)29-23(43)16(55-34)6-53-32(51)8-3-13(37)20(40)24(44)17(8)18-9(33(52)56-29)5-15(22(42)25(18)45)54-28-10(30(48)49)4-14(38)21(41)26(28)46/h1-5,16,23,27,29,34-47H,6H2,(H,48,49)/t16-,23-,27-,29+,34+/m1/s1

> <INCHI_KEY>
AJIFASHLGBHDDS-GEFDNOIESA-N

> <FORMULA>
C34H26O23

> <MOLECULAR_WEIGHT>
802.559

> <EXACT_MASS>
802.086487097

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
69.14376332957349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1S,19R,21S,22R,23R)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid

> <JCHEM_LOGP>
1.645991426666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.799429172627438

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.447286533253805

> <JCHEM_PKA_STRONGEST_BASIC>
-6.173807506695536

> <JCHEM_POLAR_SURFACE_AREA>
397.6500000000001

> <JCHEM_REFRACTIVITY>
179.7545

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1S,19R,21S,22R,23R)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       2.814   1.661   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.806   0.497   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.310  -0.958   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.822  -1.249   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.831  -0.085   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.343  -0.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.351   0.788   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.863   0.497   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.367  -0.958   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.359  -2.122   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.880  -1.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.888  -0.085   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.400  -0.376   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.408   0.788   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.904  -1.831   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.416  -2.122   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.896  -2.995   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.400  -4.450   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.384  -2.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.376  -3.868   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.863  -3.577   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.267  -4.456   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.359  -6.197   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.351  -7.361   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.855  -8.816   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.847  -9.980   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -9.689   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.327 -10.853   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.831  -8.234   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.351 -11.435   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.863 -11.726   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.367 -13.181   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.871 -10.562   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.384 -10.853   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.367  -9.107   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.376  -7.943   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.871  -6.488   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.135  -7.369   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.880  -5.323   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.392  -5.614   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.855  -4.741   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.408  -6.215   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       6.343  -4.450   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.839  -2.995   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.327  -2.704   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       3.318  -3.868   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       6.847  -1.831   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.899  -2.955   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.294   0.788   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -0.714  -0.376   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.227  -0.085   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -3.235  -1.249   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.731   1.370   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -4.243   1.661   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -1.722   2.534   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -2.227   3.990   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -0.210   2.243   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   49                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   45                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   47                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20   22   41                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   25   36                                                  
CONECT   36   35                                                            
CONECT   37   23   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   20   40                                                  
CONECT   40   39                                                            
CONECT   41   21   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   47                                                  
CONECT   45   44    4   46                                                  
CONECT   46   45                                                            
CONECT   47   44    6   48                                                  
CONECT   48   47                                                            
CONECT   49    2   50   57                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   49                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
Mallotinate	Generator

Chemical Formula

C₃₄H₂₆O₂₃

Average Mass

802.5590 Da

Monoisotopic Mass

802.08649 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(OC4=C(C=C(O)C(O)=C4O)C(O)=O)C(O)=C3O)C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2

InChI Identifier

InChI=1S/C34H26O23/c35-11-1-7(2-12(36)19(11)39)31(50)57-34-27(47)29-23(43)16(55-34)6-53-32(51)8-3-13(37)20(40)24(44)17(8)18-9(33(52)56-29)5-15(22(42)25(18)45)54-28-10(30(48)49)4-14(38)21(41)26(28)46/h1-5,16,23,27,29,34-47H,6H2,(H,48,49)/t16-,23-,27-,29+,34+/m1/s1

InChI Key

AJIFASHLGBHDDS-GEFDNOIESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cunonia macrophylla	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Mallotus japonicus	LOTUS Database	35616633
Mallotus repandus	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
Macrolide
Tetracarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
Gallic acid
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Diaryl ether
Hydroxybenzoic acid
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoic acid
Phenol ether
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tannin (CHEBI:81154 )

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	1.65	ChemAxon
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	397.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	179.75 m³·mol⁻¹	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035172

Chemspider ID

8231698

KEGG Compound ID

C17521

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10056140

PDB ID

Not Available

ChEBI ID

81154

Good Scents ID

Not Available

References

General References

Silva LN, Rigo GV, Silva DB, Carollo CA, Trentin DS, Silva MV, Tasca T, Macedo AJ: Hydrolyzable tannins from Poincianella (Caesalpinia) microphylla fruits: Metabolite profiling and anti-Trichomonas vaginalis activity. Food Res Int. 2020 Aug;134:109236. doi: 10.1016/j.foodres.2020.109236. Epub 2020 Apr 15. [PubMed:32517934 ]
Bueno FG, Panizzon GP, Mello EV, Lechtenberg M, Petereit F, de Mello JC, Hensel A: Hydrolyzable tannins from hydroalcoholic extract from Poincianella pluviosa stem bark and its wound-healing properties: phytochemical investigations and influence on in vitro cell physiology of human keratinocytes and dermal fibroblasts. Fitoterapia. 2014 Dec;99:252-60. doi: 10.1016/j.fitote.2014.10.007. Epub 2014 Oct 16. [PubMed:25454458 ]
Tabata H, Katsube T, Tsuma T, Ohta Y, Imawaka N, Utsumi T: Isolation and evaluation of the radical-scavenging activity of the antioxidants in the leaves of an edible plant, Mallotus japonicus. Food Chem. 2008 Jul 1;109(1):64-71. doi: 10.1016/j.foodchem.2007.12.017. Epub 2007 Dec 16. [PubMed:26054265 ]
Fogliani B, Raharivelomanana P, Bianchini JP, Bouraima-Madjebi S, Hnawia E: Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia. Phytochemistry. 2005 Jan;66(2):241-7. doi: 10.1016/j.phytochem.2004.11.016. [PubMed:15652581 ]
LOTUS database [Link]

Showing NP-Card for 2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid (NP0304476)

MOL for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

3D MOL for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

3D SDF for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

3D-SDF for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

PDB for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

3D PDB for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

SMILES for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

INCHI for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

Structure for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)

3D Structure for NP0304476 (2-{[(1s,19r,21s,22r,23r)-7,8,11,12,13,22,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxybenzoic acid)