NP-MRD: Showing NP-Card for Thonningianin A (NP0060795)

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Record Information

Version

2.0

Created at

2022-04-28 05:46:45 UTC

Updated at

2022-04-28 05:46:45 UTC

NP-MRD ID

NP0060795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thonningianin A

Description

(10S,11R,12S,13R,15R)-13-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate 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. Thonningianin A is found in Thonningia sanguinea . Based on a literature review very few articles have been published on (10S,11R,12S,13R,15R)-13-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207462D          

 63 69  0  0  1  0            999 V2000
    8.5786    4.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3445    4.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4619    3.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8134    2.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0475    3.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301    3.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1642    4.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9308    2.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2823    1.5196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5164    1.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8679    1.3162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9853    0.4996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7512    0.1930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3997    0.7030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1656    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8686   -0.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6345   -0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2830   -0.4203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7519   -1.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5178   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6353   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9868   -3.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2209   -3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1034   -2.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5724   -3.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -4.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4012   -3.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6426   -0.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9486   -0.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1236   -0.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295   -0.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962   -0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570   -1.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0022   -0.1829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898    1.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724    0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3209    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5912   -0.1920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1413    2.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7445    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    2.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5361    2.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930    4.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4612    5.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6953    5.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1096    5.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9922    6.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6407    7.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5233    7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1718    8.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9377    8.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0551    7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4066    6.8259    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  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  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 21 27  1  0  0  0  0
 12 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
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 32 40  1  0  0  0  0
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 51 52  1  0  0  0  0
 11 52  1  0  0  0  0
  2 53  1  0  0  0  0
  1 54  1  0  0  0  0
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 57 58  1  0  0  0  0
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 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 58 63  1  0  0  0  0
M  END

     RDKit          3D

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 63 97  1  0
M  END


  Mrv1652304282207462D          

 63 69  0  0  1  0            999 V2000
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    8.8134    2.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0868    0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898    1.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724    0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3209    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5912   -0.1920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1413    2.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7445    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    2.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5361    2.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930    4.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4612    5.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6953    5.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1096    5.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9922    6.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6407    7.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5233    7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1718    8.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9377    8.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0551    7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4066    6.8259    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
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  1  6  1  0  0  0  0
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  4  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
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 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  1  0  0  0
 16 17  1  0  0  0  0
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 28 29  1  0  0  0  0
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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
 33 39  1  0  0  0  0
 32 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
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 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
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 43 48  1  0  0  0  0
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 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 11 52  1  0  0  0  0
  2 53  1  0  0  0  0
  1 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 58 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](OC2=CC(O)=C(C(=O)CCC3=CC=CC=C3)C(O)=C2)O[C@@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]2[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C42H34O21/c43-20(7-6-15-4-2-1-3-5-15)30-21(44)10-17(11-22(30)45)60-42-36(55)38(63-39(56)16-8-23(46)31(50)24(47)9-16)37-27(61-42)14-59-40(57)18-12-25(48)32(51)34(53)28(18)29-19(41(58)62-37)13-26(49)33(52)35(29)54/h1-5,8-13,27,36-38,42,44-55H,6-7,14H2/t27-,36+,37+,38-,42+/m1/s1

> <INCHI_KEY>
XQVKQEFQGYTUAR-AGXLSSRKSA-N

> <FORMULA>
C42H34O21

> <MOLECULAR_WEIGHT>
874.713

> <EXACT_MASS>
874.159258115

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
81.76027358362116

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,11R,12S,13R,15R)-13-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
5.958828958

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.917054518113178

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.4190123867687365

> <JCHEM_PKA_STRONGEST_BASIC>
-4.661635533756596

> <JCHEM_POLAR_SURFACE_AREA>
357.19

> <JCHEM_REFRACTIVITY>
210.24309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S,11R,12S,13R,15R)-13-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <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  C   UNK     0      16.013   8.361   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.443   7.789   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.662   6.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.452   5.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.022   5.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.803   7.409   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.373   7.982   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.671   3.788   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.460   2.837   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.031   3.409   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.820   2.457   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.039   0.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.469   0.360   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.679   1.312   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.109   0.740   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.688  -1.164   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.118  -1.736   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.328  -0.784   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.337  -3.261   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.767  -3.833   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.986  -5.357   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.775  -6.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.346  -5.737   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.126  -4.213   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.135  -6.689   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      16.994  -7.834   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      19.415  -5.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.400  -0.468   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.104  -1.301   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.538  -2.778   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.564  -1.301   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.268  -0.468   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.900  -1.174   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.826  -2.712   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.122  -3.545   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.491  -2.839   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.049  -5.083   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.458  -3.418   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.604  -0.341   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.629   0.933   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.848   2.457   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.637   3.409   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.208   2.837   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.989   1.312   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.199   0.360   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.837  -0.358   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       3.559   0.740   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       3.997   3.788   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.856   3.621   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       8.024   4.916   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      10.334   4.055   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      11.812   3.621   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      18.654   8.741   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      15.794   9.886   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      14.364  10.458   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      17.005  10.838   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      16.786  12.362   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      17.996  13.314   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      17.777  14.838   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.987  15.790   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      20.417  15.218   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      20.636  13.694   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      19.426  12.742   0.000  0.00  0.00           C+0
CONECT    1    2    6   54                                                  
CONECT    2    1    3   53                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   52                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   22                                                            
CONECT   27   21                                                            
CONECT   28   12   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33   40                                                  
CONECT   33   32   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35                                                            
CONECT   38   34                                                            
CONECT   39   33                                                            
CONECT   40   32   41   45                                                  
CONECT   41   40   42   49                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   47                                                  
CONECT   45   44   40   46                                                  
CONECT   46   45                                                            
CONECT   47   44                                                            
CONECT   48   43                                                            
CONECT   49   41   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   11                                                       
CONECT   53    2                                                            
CONECT   54    1   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   58                                                       
MASTER        0    0    0    0    0    0    0    0   63    0  138    0
END

View in JSmol

Synonyms

Value	Source
(10S,11R,12S,13R,15R)-13-[3,5-Dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0,.0,]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₄₂H₃₄O₂₁

Average Mass

874.7130 Da

Monoisotopic Mass

874.15926 Da

IUPAC Name

(10S,11R,12S,13R,15R)-13-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-11-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](OC2=CC(O)=C(C(=O)CCC3=CC=CC=C3)C(O)=C2)O[C@@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]2[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C42H34O21/c43-20(7-6-15-4-2-1-3-5-15)30-21(44)10-17(11-22(30)45)60-42-36(55)38(63-39(56)16-8-23(46)31(50)24(47)9-16)37-27(61-42)14-59-40(57)18-12-25(48)32(51)34(53)28(18)29-19(41(58)62-37)13-26(49)33(52)35(29)54/h1-5,8-13,27,36-38,42,44-55H,6-7,14H2/t27-,36+,37+,38-,42+/m1/s1

InChI Key

XQVKQEFQGYTUAR-AGXLSSRKSA-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
Thonningia sanguinea	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
Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Phenolic glycoside
Cinnamylphenol
Linear 1,3-diarylpropanoid
Alkyl-phenylketone
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Butyrophenone
Benzoate ester
Phenylketone
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	3.69	ALOGPS
logP	5.96	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	357.19 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	210.24 m³·mol⁻¹	ChemAxon
Polarizability	81.76 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

162882842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Thonningianin A (NP0060795)

MOL for NP0060795 (Thonningianin A)

3D MOL for NP0060795 (Thonningianin A)

3D SDF for NP0060795 (Thonningianin A)

3D-SDF for NP0060795 (Thonningianin A)

PDB for NP0060795 (Thonningianin A)

3D PDB for NP0060795 (Thonningianin A)

SMILES for NP0060795 (Thonningianin A)

INCHI for NP0060795 (Thonningianin A)

Structure for NP0060795 (Thonningianin A)

3D Structure for NP0060795 (Thonningianin A)