NP-MRD: Showing NP-Card for Hirtellin G (NP0074259)

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Record Information

Version

2.0

Created at

2022-04-28 19:24:53 UTC

Updated at

2022-04-28 19:24:53 UTC

NP-MRD ID

NP0074259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hirtellin G

Description

(2S,3S,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 2-[5-({[(10R,11R,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-13-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-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. Hirtellin G is found in Reaumuria hirtella. Based on a literature review very few articles have been published on (2S,3S,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 2-[5-({[(10R,11R,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-13-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221242D          

112122  0  0  1  0            999 V2000
    7.5219   11.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2878   11.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4052   10.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7567   10.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9908   10.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8734   11.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1075   11.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3423    9.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1711   10.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8196   10.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2885    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0544    9.2757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1718    8.4591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5233    7.9491    0.0000 O   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
   10.4066    6.8259    0.0000 O   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
    8.2263    6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8756    5.4993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930    4.6827    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
   10.2278    3.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8763    3.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0868    4.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5833    4.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6422    3.2529    0.0000 O   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 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  2  0  0  0  0  0  0  0  0  0
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    7.7512    0.1930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.1656    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8141    0.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6967    1.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5800    0.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2285    1.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9944    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1118   -0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4633   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6974   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5807   -1.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8777   -0.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6429    1.3130    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
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    8.7519   -1.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    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
    4.7445    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3276    1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8119    6.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9377    8.1525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5862    8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4688    9.4791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7029    9.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9999   10.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0551    7.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8210    7.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4695    7.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5877    4.7828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  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
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  1  6  1  0  0  0  0
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M  END

     RDKit          3D

164174  0  0  0  0  0  0  0  0999 V2000
   10.7446    1.0844    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2340    0.9598    1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8179    1.0987    1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221242D          

112122  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0074259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2OC2=CC(=CC(O)=C2O)C(=O)O[C@@H]2O[C@@H]3COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)O[C@H]3[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C68H52O44/c69-14-37-49(90)55(107-59(94)16-1-24(70)41(82)25(71)2-16)57(67(104-37)111-62(97)19-7-30(76)44(85)31(77)8-19)110-66(101)23-13-35(81)48(89)52(93)53(23)103-36-10-20(9-32(78)45(36)86)63(98)112-68-58(109-61(96)18-5-28(74)43(84)29(75)6-18)56(108-60(95)17-3-26(72)42(83)27(73)4-17)54-38(105-68)15-102-64(99)21-11-33(79)46(87)50(91)39(21)40-22(65(100)106-54)12-34(80)47(88)51(40)92/h1-13,37-38,49,54-58,67-93H,14-15H2/t37-,38-,49+,54-,55-,56-,57+,58-,67+,68+/m1/s1

> <INCHI_KEY>
DZNMCCYNKMCFSE-ZBFMVUNASA-N

> <FORMULA>
C68H52O44

> <MOLECULAR_WEIGHT>
1573.12

> <EXACT_MASS>
1572.183144954

> <JCHEM_ACCEPTOR_COUNT>
35

> <JCHEM_ATOM_COUNT>
164

> <JCHEM_AVERAGE_POLARIZABILITY>
140.4689743043877

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
25

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 2-[5-({[(10R,11R,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-13-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
5.9163388679999995

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.357852984283904

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.906455710645999

> <JCHEM_PKA_STRONGEST_BASIC>
-5.910946773099735

> <JCHEM_POLAR_SURFACE_AREA>
743.8400000000004

> <JCHEM_REFRACTIVITY>
355.24449999999973

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 2-[5-({[(10R,11R,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-13-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-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      14.041  22.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.471  21.508   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.690  19.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.479  19.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.049  19.604   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.830  21.128   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.401  21.701   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.839  18.652   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      17.119  19.411   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.330  20.363   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.339  17.887   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.768  17.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.987  15.790   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.777  14.838   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.996  13.314   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      19.426  12.742   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.786  12.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.356  12.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.145  11.982   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.364  10.458   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.794   9.886   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.005  10.838   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.434  10.265   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.654   8.741   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.443   7.789   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.662   6.265   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.092   5.692   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.302   6.644   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.695   8.397   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      21.622   8.227   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      21.732   6.072   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.452   5.313   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.022   5.885   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.671   3.788   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.460   2.837   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.031   3.409   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.820   2.457   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.039   0.933   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.469   0.360   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      15.679   1.312   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      17.109   0.740   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      18.320   1.692   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      18.101   3.216   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      19.749   1.119   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.960   2.071   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      22.390   1.499   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      22.609  -0.025   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      21.398  -0.977   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      19.969  -0.405   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      21.617  -2.502   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      24.038  -0.598   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      23.600   2.451   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      14.688  -1.164   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      16.118  -1.736   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      17.328  -0.784   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      16.337  -3.261   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      17.767  -3.833   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      17.986  -5.357   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      16.775  -6.309   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      15.346  -5.737   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      15.126  -4.213   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      14.135  -6.689   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      16.994  -7.834   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      19.415  -5.930   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      12.400  -0.468   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      11.104  -1.301   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      11.538  -2.778   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0       9.564  -1.301   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       8.268  -0.468   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       7.629   0.933   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       7.848   2.457   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       8.856   3.621   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0       8.024   4.916   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      10.334   4.055   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      11.812   3.621   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       6.637   3.409   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       5.208   2.837   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       4.989   1.312   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       6.199   0.360   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0       5.980  -1.164   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0       3.559   0.740   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0       3.997   3.788   0.000  0.00  0.00           O+0
HETATM   83  C   UNK     0       6.900  -1.174   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       6.826  -2.712   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       8.122  -3.545   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0       9.491  -2.839   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0       8.049  -5.083   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0       5.458  -3.418   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0       5.465  -1.733   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0      16.013   8.361   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0      13.154   9.506   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      12.716  12.555   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0      20.417  15.218   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      21.628  16.170   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      21.408  17.694   0.000  0.00  0.00           C+0
HETATM   96  O   UNK     0      19.979  18.267   0.000  0.00  0.00           O+0
HETATM   97  C   UNK     0      22.619  18.646   0.000  0.00  0.00           C+0
HETATM   98  O   UNK     0      22.400  20.171   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0      23.057  15.598   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0      20.636  13.694   0.000  0.00  0.00           O+0
HETATM  101  C   UNK     0      22.066  13.121   0.000  0.00  0.00           C+0
HETATM  102  O   UNK     0      23.276  14.073   0.000  0.00  0.00           O+0
HETATM  103  C   UNK     0      22.285  11.597   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      23.715  11.025   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      23.934   9.500   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      22.723   8.548   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      21.294   9.121   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      21.075  10.645   0.000  0.00  0.00           C+0
HETATM  109  O   UNK     0      20.083   8.169   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0      22.943   7.024   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0      25.364   8.928   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0      13.822  23.605   0.000  0.00  0.00           O+0
CONECT    1    2    6  112                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    3   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   96                                                  
CONECT   13   12   14   93                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   92                                                  
CONECT   20   19   21   91                                                  
CONECT   21   20   22   90                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   26   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   75                                                  
CONECT   38   37   39   65                                                  
CONECT   39   38   40   53                                                  
CONECT   40   39   35   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   52                                                  
CONECT   47   46   48   51                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48   44                                                       
CONECT   50   48                                                            
CONECT   51   47                                                            
CONECT   52   46                                                            
CONECT   53   39   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   64                                                  
CONECT   59   58   60   63                                                  
CONECT   60   59   61   62                                                  
CONECT   61   60   56                                                       
CONECT   62   60                                                            
CONECT   63   59                                                            
CONECT   64   58                                                            
CONECT   65   38   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69   86                                                  
CONECT   69   68   70   83                                                  
CONECT   70   69   71   79                                                  
CONECT   71   70   72   76                                                  
CONECT   72   71   73   74                                                  
CONECT   73   72                                                            
CONECT   74   72   75                                                       
CONECT   75   74   37                                                       
CONECT   76   71   77                                                       
CONECT   77   76   78   82                                                  
CONECT   78   77   79   81                                                  
CONECT   79   78   70   80                                                  
CONECT   80   79                                                            
CONECT   81   78                                                            
CONECT   82   77                                                            
CONECT   83   69   84   89                                                  
CONECT   84   83   85   88                                                  
CONECT   85   84   86   87                                                  
CONECT   86   85   68                                                       
CONECT   87   85                                                            
CONECT   88   84                                                            
CONECT   89   83                                                            
CONECT   90   21                                                            
CONECT   91   20                                                            
CONECT   92   19                                                            
CONECT   93   13   94  100                                                  
CONECT   94   93   95   99                                                  
CONECT   95   94   96   97                                                  
CONECT   96   95   12                                                       
CONECT   97   95   98                                                       
CONECT   98   97                                                            
CONECT   99   94                                                            
CONECT  100   93  101                                                       
CONECT  101  100  102  103                                                  
CONECT  102  101                                                            
CONECT  103  101  104  108                                                  
CONECT  104  103  105                                                       
CONECT  105  104  106  111                                                  
CONECT  106  105  107  110                                                  
CONECT  107  106  108  109                                                  
CONECT  108  107  103                                                       
CONECT  109  107                                                            
CONECT  110  106                                                            
CONECT  111  105                                                            
CONECT  112    1                                                            
MASTER        0    0    0    0    0    0    0    0  112    0  244    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R,5S,6R)-5-Hydroxy-6-(hydroxymethyl)-2,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-3-yl 2-[5-({[(10R,11R,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0,.0,]tricosa-1(23),2,4,6,19,21-hexaen-13-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₆₈H₅₂O₄₄

Average Mass

1573.1200 Da

Monoisotopic Mass

1572.18314 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2OC2=CC(=CC(O)=C2O)C(=O)O[C@@H]2O[C@@H]3COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)O[C@H]3[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1O

InChI Identifier

InChI=1S/C68H52O44/c69-14-37-49(90)55(107-59(94)16-1-24(70)41(82)25(71)2-16)57(67(104-37)111-62(97)19-7-30(76)44(85)31(77)8-19)110-66(101)23-13-35(81)48(89)52(93)53(23)103-36-10-20(9-32(78)45(36)86)63(98)112-68-58(109-61(96)18-5-28(74)43(84)29(75)6-18)56(108-60(95)17-3-26(72)42(83)27(73)4-17)54-38(105-68)15-102-64(99)21-11-33(79)46(87)50(91)39(21)40-22(65(100)106-54)12-34(80)47(88)51(40)92/h1-13,37-38,49,54-58,67-93H,14-15H2/t37-,38-,49+,54-,55-,56-,57+,58-,67+,68+/m1/s1

InChI Key

DZNMCCYNKMCFSE-ZBFMVUNASA-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
Reaumuria hirtella	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
Diphenylether
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Diaryl ether
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Phenoxy compound
Phenol ether
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	4.06	ALOGPS
logP	5.92	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	5.91	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	35	ChemAxon
Hydrogen Donor Count	25	ChemAxon
Polar Surface Area	743.84 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	355.24 m³·mol⁻¹	ChemAxon
Polarizability	140.47 Å³	ChemAxon
Number of Rings	11	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

162910138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hirtellin G (NP0074259)

MOL for NP0074259 (Hirtellin G)

3D MOL for NP0074259 (Hirtellin G)

3D SDF for NP0074259 (Hirtellin G)

3D-SDF for NP0074259 (Hirtellin G)

PDB for NP0074259 (Hirtellin G)

3D PDB for NP0074259 (Hirtellin G)

SMILES for NP0074259 (Hirtellin G)

INCHI for NP0074259 (Hirtellin G)

Structure for NP0074259 (Hirtellin G)

3D Structure for NP0074259 (Hirtellin G)