NP-MRD: Showing NP-Card for Theograndin I (NP0026735)

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Record Information

Version

2.0

Created at

2021-06-19 18:32:57 UTC

Updated at

2021-06-29 23:52:27 UTC

NP-MRD ID

NP0026735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Theograndin I

Provided By

JEOL Database JEOL Logo

Description

Theograndin I is found in Theobroma grandiflorum. Theograndin I was first documented in 2003 (Yang, H., et al.). Based on a literature review very few articles have been published on THEOGRANDIN I.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120323D          

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     RDKit          3D

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  Mrv1652306192120323D          

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   -2.9116   -1.7388    1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -4.4472   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995   -4.7406   -3.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6714   -2.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.3673    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6810    2.3319    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414    4.2259   -1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9841    2.8874   -3.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9439   -3.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371    1.2897    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934    0.3804    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484    1.9534    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438    4.4259    0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196    3.7920    1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    5.0261   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  9  8  2  0  0  0  0
 15 17  1  0  0  0  0
  9 10  1  0  0  0  0
 17 18  2  0  0  0  0
  8  7  1  0  0  0  0
 18 26  1  0  0  0  0
 22 23  1  0  0  0  0
  9 11  1  0  0  0  0
 19 20  2  0  0  0  0
 11 12  2  0  0  0  0
 20 21  1  0  0  0  0
 12 14  1  0  0  0  0
 21 22  2  0  0  0  0
 27  8  1  0  0  0  0
 22 24  1  0  0  0  0
 27 14  2  0  0  0  0
 28 30  1  0  0  0  0
 28  6  1  0  0  0  0
  5  4  1  0  0  0  0
  4 36  1  0  0  0  0
 36 30  1  0  0  0  0
  6  7  1  0  0  0  0
 28 29  1  0  0  0  0
 24 25  2  0  0  0  0
  2  1  2  0  0  0  0
 25 19  1  0  0  0  0
  2  3  1  0  0  0  0
 18 19  1  0  0  0  0
 32 31  1  1  0  0  0
 27 26  1  0  0  0  0
 32 35  1  0  0  0  0
 15 16  2  0  0  0  0
 32 33  2  0  0  0  0
 14 15  1  0  0  0  0
 32 34  2  0  0  0  0
  6  5  1  0  0  0  0
 30 31  1  0  0  0  0
 36 37  1  0  0  0  0
  4  2  1  0  0  0  0
 11 42  1  0  0  0  0
 17 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 24 48  1  0  0  0  0
 25 49  1  0  0  0  0
 13 43  1  0  0  0  0
 10 41  1  0  0  0  0
 23 47  1  0  0  0  0
 30 52  1  6  0  0  0
 37 55  1  0  0  0  0
 36 54  1  1  0  0  0
  6 40  1  6  0  0  0
 28 50  1  1  0  0  0
 29 51  1  0  0  0  0
  4 39  1  6  0  0  0
  3 38  1  0  0  0  0
 35 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])O[C@@]([H])(OC2=C(O[H])C([H])=C(O[H])C3=C2OC(=C([H])C3=O)C2=C([H])C([H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[S](=O)(=O)O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1

> <INCHI_KEY>
RUJCBFMBNQPWBK-DLSLMLROSA-N

> <FORMULA>
C21H18O15S

> <MOLECULAR_WEIGHT>
542.42

> <EXACT_MASS>
542.036641054

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
47.85026238091024

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
-1.5757164955993448

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.4395053760720424

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.3911854248739077

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7663500856824443

> <JCHEM_POLAR_SURFACE_AREA>
246.80999999999995

> <JCHEM_REFRACTIVITY>
116.8984

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.7754    4.8638   -1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4874    3.7152   -1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771    3.2410   -1.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    2.6835   -0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8314    1.5757   -0.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    0.5368    0.2538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9659   -0.5296    0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068   -1.5676   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -2.5822   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8964   -2.5544    0.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -3.6609   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560   -3.7274   -1.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -4.8089   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -2.7180   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -2.7551   -2.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9245   -3.6763   -3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -1.6375   -2.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824   -0.6549   -1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798    0.4959   -1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049    0.9096   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274    2.0183    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201    2.7235   -0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139    3.8024   -0.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072    2.3369   -2.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870    1.2236   -2.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -0.6195   -0.7217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -1.6390   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874    1.0475    1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6150    0.0010    1.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356    2.2746    0.8264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1443    2.8683    1.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988    3.2950    1.7103 S   0  0  2  0  0  6  0  0  0  0  0  0
   -5.9628    4.3960    2.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4699    2.0734    1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    3.8780    0.2093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    3.3328    0.2620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2830    4.3760   -0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8020    2.3160   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415    2.3587   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000    0.1818   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -1.7388    1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -4.4472   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995   -4.7406   -3.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6714   -2.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.3673    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6810    2.3319    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414    4.2259   -1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9841    2.8874   -3.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9439   -3.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371    1.2897    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934    0.3804    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484    1.9534    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438    4.4259    0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196    3.7920    1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    5.0261   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  9  8  2  0
 15 17  1  0
  9 10  1  0
 17 18  2  0
  8  7  1  0
 18 26  1  0
 22 23  1  0
  9 11  1  0
 19 20  2  0
 11 12  2  0
 20 21  1  0
 12 14  1  0
 21 22  2  0
 27  8  1  0
 22 24  1  0
 27 14  2  0
 28 30  1  0
 28  6  1  0
  5  4  1  0
  4 36  1  0
 36 30  1  0
  6  7  1  0
 28 29  1  0
 24 25  2  0
  2  1  2  0
 25 19  1  0
  2  3  1  0
 18 19  1  0
 32 31  1  1
 27 26  1  0
 32 35  1  0
 15 16  2  0
 32 33  2  0
 14 15  1  0
 32 34  2  0
  6  5  1  0
 30 31  1  0
 36 37  1  0
  4  2  1  0
 11 42  1  0
 17 44  1  0
 20 45  1  0
 21 46  1  0
 24 48  1  0
 25 49  1  0
 13 43  1  0
 10 41  1  0
 23 47  1  0
 30 52  1  6
 37 55  1  0
 36 54  1  1
  6 40  1  6
 28 50  1  1
 29 51  1  0
  4 39  1  6
  3 38  1  0
 35 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.775   4.864  -1.481  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.487   3.715  -1.170  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.777   3.241  -1.168  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.525   2.684  -0.748  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.831   1.576  -0.164  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.723   0.537   0.254  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.966  -0.530   0.847  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.807  -1.568  -0.031  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.764  -2.582  -0.089  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.896  -2.554   0.674  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.595  -3.661  -0.952  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.456  -3.727  -1.753  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.348  -4.809  -2.584  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.512  -2.718  -1.689  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.721  -2.755  -2.522  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.925  -3.676  -3.305  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.666  -1.638  -2.386  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.382  -0.655  -1.520  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.280   0.496  -1.324  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.605   0.910  -0.023  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.427   2.018   0.186  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.920   2.724  -0.905  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.714   3.802  -0.655  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.607   2.337  -2.203  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.787   1.224  -2.411  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.253  -0.620  -0.722  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.341  -1.639  -0.825  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.687   1.048   1.342  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.615   0.001   1.679  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.436   2.275   0.826  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.144   2.868   1.913  0.00  0.00           O+0
HETATM   32  S   UNK     0      -5.699   3.295   1.710  0.00  0.00           S+0
HETATM   33  O   UNK     0      -5.963   4.396   2.606  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.470   2.073   1.742  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.750   3.878   0.209  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.479   3.333   0.262  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.283   4.376  -0.326  0.00  0.00           O+0
HETATM   38  H   UNK     0       0.802   2.316  -0.827  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.042   2.359  -1.659  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.300   0.182  -0.614  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.912  -1.739   1.218  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.343  -4.447  -0.999  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.500  -4.741  -3.080  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.561  -1.671  -2.994  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.227   0.367   0.842  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.681   2.332   1.194  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.941   4.226  -1.499  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.984   2.887  -3.059  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.537   0.944  -3.433  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.137   1.290   2.259  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.293   0.380   2.275  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.148   1.953   0.055  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.944   4.426   0.042  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.920   3.792   1.087  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.654   5.026  -0.724  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   38                                                       
CONECT    4    5   36    2   39                                             
CONECT    5    4    6                                                       
CONECT    6   28    7    5   40                                             
CONECT    7    8    6                                                       
CONECT    8    9    7   27                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   41                                                       
CONECT   11    9   12   42                                                  
CONECT   12   13   11   14                                                  
CONECT   13   12   43                                                       
CONECT   14   12   27   15                                                  
CONECT   15   17   16   14                                                  
CONECT   16   15                                                            
CONECT   17   15   18   44                                                  
CONECT   18   17   26   19                                                  
CONECT   19   20   25   18                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22   46                                                  
CONECT   22   23   21   24                                                  
CONECT   23   22   47                                                       
CONECT   24   22   25   48                                                  
CONECT   25   24   19   49                                                  
CONECT   26   18   27                                                       
CONECT   27    8   14   26                                                  
CONECT   28   30    6   29   50                                             
CONECT   29   28   51                                                       
CONECT   30   28   36   31   52                                             
CONECT   31   32   30                                                       
CONECT   32   31   35   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   53                                                       
CONECT   36    4   30   37   54                                             
CONECT   37   36   55                                                       
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    6                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   17                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   37                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
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   -0.4874    3.7152   -1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771    3.2410   -1.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    2.6835   -0.7480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8314    1.5757   -0.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7644   -2.5822   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8964   -2.5544    0.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -3.6609   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560   -3.7274   -1.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -4.8089   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2798    0.4959   -1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049    0.9096   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274    2.0183    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201    2.7235   -0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139    3.8024   -0.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072    2.3369   -2.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870    1.2236   -2.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533   -0.6195   -0.7217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -1.6390   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874    1.0475    1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6150    0.0010    1.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356    2.2746    0.8264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1443    2.8683    1.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988    3.2950    1.7103 S   0  0  2  0  0  6  0  0  0  0  0  0
   -5.9628    4.3960    2.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4699    2.0734    1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    3.8780    0.2093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    3.3328    0.2620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2830    4.3760   -0.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8020    2.3160   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415    2.3587   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000    0.1818   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -1.7388    1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -4.4472   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995   -4.7406   -3.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6714   -2.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.3673    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6810    2.3319    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414    4.2259   -1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9841    2.8874   -3.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9439   -3.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371    1.2897    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934    0.3804    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484    1.9534    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438    4.4259    0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196    3.7920    1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    5.0261   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  9  8  2  0
 15 17  1  0
  9 10  1  0
 17 18  2  0
  8  7  1  0
 18 26  1  0
 22 23  1  0
  9 11  1  0
 19 20  2  0
 11 12  2  0
 20 21  1  0
 12 14  1  0
 21 22  2  0
 27  8  1  0
 22 24  1  0
 27 14  2  0
 28 30  1  0
 28  6  1  0
  5  4  1  0
  4 36  1  0
 36 30  1  0
  6  7  1  0
 28 29  1  0
 24 25  2  0
  2  1  2  0
 25 19  1  0
  2  3  1  0
 18 19  1  0
 32 31  1  1
 27 26  1  0
 32 35  1  0
 15 16  2  0
 32 33  2  0
 14 15  1  0
 32 34  2  0
  6  5  1  0
 30 31  1  0
 36 37  1  0
  4  2  1  0
 11 42  1  0
 17 44  1  0
 20 45  1  0
 21 46  1  0
 24 48  1  0
 25 49  1  0
 13 43  1  0
 10 41  1  0
 23 47  1  0
 30 52  1  6
 37 55  1  0
 36 54  1  1
  6 40  1  6
 28 50  1  1
 29 51  1  0
  4 39  1  6
  3 38  1  0
 35 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₁₅S

Average Mass

542.4200 Da

Monoisotopic Mass

542.03664 Da

IUPAC Name

(2S,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

Traditional Name

(2S,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1([H])O[C@@]([H])(OC2=C(O[H])C([H])=C(O[H])C3=C2OC(=C([H])C3=O)C2=C([H])C([H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[S](=O)(=O)O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1

InChI Key

RUJCBFMBNQPWBK-DLSLMLROSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Theobroma grandiflorum	JEOL database	Yang, H., et al, J. Nat. Prod. 66, 1501 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glucuronides

Alternative Parents

Substituents

Flavonoid-8-o-glucuronide
Flavonoid-8-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Pyranone
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Sulfuric acid monoester
Alkyl sulfate
Pyran
Oxane
Sulfuric acid ester
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Sulfate-ester
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Organic sulfuric acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.58	ALOGPS
logP	-1.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	246.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.9 m³·mol⁻¹	ChemAxon
Polarizability	47.85 Å³	ChemAxon
Number of Rings	4	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

9332093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11156985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang, H., et al. (2003). Yang, H., et al, J. Nat. Prod. 66, 1501 (2003). J. Nat. Prod..

Showing NP-Card for Theograndin I (NP0026735)

MOL for NP0026735 (Theograndin I)

3D MOL for NP0026735 (Theograndin I)

3D SDF for NP0026735 (Theograndin I)

3D-SDF for NP0026735 (Theograndin I)

PDB for NP0026735 (Theograndin I)

3D PDB for NP0026735 (Theograndin I)

SMILES for NP0026735 (Theograndin I)

INCHI for NP0026735 (Theograndin I)

Structure for NP0026735 (Theograndin I)

3D Structure for NP0026735 (Theograndin I)