NP-MRD: Showing NP-Card for (+)-Kurigalin (NP0078543)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 23:36:27 UTC

Updated at

2022-04-28 23:36:27 UTC

NP-MRD ID

NP0078543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Kurigalin

Description

(2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. (+)-Kurigalin is found in Castanea crenata and Castanea sativa Mill. . Based on a literature review very few articles have been published on (2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201362D          

 45 47  0  0  1  0            999 V2000
   -1.6796   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -5.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -5.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8927   -5.8559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6072   -5.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0197   -6.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -6.8724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -1.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -4.6184    0.0000 O   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
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 22 28  1  0  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 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
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 35 41  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  2  0  0  0  0
 15 44  1  6  0  0  0
 14 45  1  1  0  0  0
M  END

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
   -1.1844   -2.7334    2.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185   -1.7859    1.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -1.6578    0.1762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4059   -0.5965   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655    0.6944    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    1.2039    1.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883    0.4238    2.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002    2.6289    1.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438    3.0751    3.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    4.4212    3.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    4.8880    4.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2474    5.3149    2.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705    6.6609    2.8106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    4.8750    1.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0766    5.7999    0.2074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770    3.5434    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0270   -2.8873   -0.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -3.1299   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352   -2.2927   -2.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -4.4380   -1.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156   -4.6837   -3.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2127   -5.8976   -3.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6896   -6.1332   -4.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -6.8918   -2.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9350   -8.1221   -2.7604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600   -6.6452   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9872   -7.6557   -0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2651   -5.4339   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -1.5587   -0.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6288   -2.7263   -0.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -0.3852   -0.4339 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1135    0.8412   -0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.4773   -1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    0.5092   -1.1061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5436    0.6966    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -0.0590    1.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5067    1.7892    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820    2.6360   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112    3.6645   -0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903    4.5179   -1.8358 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3944    3.8577    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3179    4.9002    0.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203    3.0141    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7646    3.1651    2.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1831    1.9872    1.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896   -1.0182    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085   -0.9857    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541   -0.4684   -1.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    2.3971    4.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488    4.3283    5.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118    7.3026    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0932    5.5856   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    3.2388   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160   -3.8965   -3.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5968   -5.4042   -5.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2726   -8.2575   -3.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4123   -8.5304   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8989   -5.2653    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633   -1.5787   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -3.5202   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.3783    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    1.4099   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295   -1.5180   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5591   -0.3942   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    2.4888   -1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6673    5.2496   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8256    5.0787    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4537    3.8642    2.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.3547    2.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
 31 29  1  0
 29 30  1  0
 29  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
  3 17  1  6
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
  3  2  1  0
  2  1  2  0
 45 37  1  0
 16  8  1  0
 28 20  1  0
 32 62  1  0
 31 61  1  1
 33 63  1  0
 33 64  1  0
 38 65  1  0
 40 66  1  0
 42 67  1  0
 44 68  1  0
 45 69  1  0
 29 59  1  6
 30 60  1  0
  4 47  1  0
  4 48  1  0
  9 49  1  0
 11 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 21 54  1  0
 23 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
  2 46  1  0
M  END


  Mrv1652304292201362D          

 45 47  0  0  1  0            999 V2000
   -1.6796   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -5.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -5.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8927   -5.8559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6072   -5.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0197   -6.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -6.8724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -4.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4322   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -1.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -4.6184    0.0000 O   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
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 22 28  1  0  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 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
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 35 41  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  2  0  0  0  0
 15 44  1  6  0  0  0
 14 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](COC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](O)[C@@](COC(=O)C1=CC(O)=C(O)C(O)=C1)(OC(=O)C1=CC(O)=C(O)C(O)=C1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O18/c28-8-27(45-26(42)12-5-17(33)22(38)18(34)6-12,9-44-25(41)11-3-15(31)21(37)16(32)4-11)23(39)19(35)7-43-24(40)10-1-13(29)20(36)14(30)2-10/h1-6,8,19,23,29-39H,7,9H2/t19-,23-,27-/m1/s1

> <INCHI_KEY>
XIOBKZGXHBXTMP-AUZMWRNASA-N

> <FORMULA>
C27H24O18

> <MOLECULAR_WEIGHT>
636.471

> <EXACT_MASS>
636.096263933

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.067799548677044

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.2016419493333323

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.111376496359135

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.63418629136723

> <JCHEM_PKA_STRONGEST_BASIC>
-5.54890221641669

> <JCHEM_POLAR_SURFACE_AREA>
318.49999999999994

> <JCHEM_REFRACTIVITY>
144.93420000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -3.135  -8.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.135 -10.161   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.469 -10.931   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.803 -10.161   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.803  -8.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.469  -7.851   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.469  -6.311   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.136  -7.851   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -7.136 -10.931   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.802 -10.931   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.802 -12.471   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.468 -10.161   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.866 -10.931   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.199 -10.161   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.533 -10.931   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.867 -10.161   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.637 -11.495   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.177 -11.495   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.947 -12.828   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.947 -10.161   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.177  -8.827   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.947  -7.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.487  -7.494   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.257  -8.827   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.487 -10.161   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.797  -8.827   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.257  -6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.177  -6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.097  -8.827   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.867  -7.494   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.097  -6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.557  -6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.867  -4.826   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.097  -3.493   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.867  -2.159   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.407  -2.159   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.177  -3.493   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.407  -4.826   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.717  -3.493   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.177  -0.825   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.097  -0.825   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.200  -9.391   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.200  -7.851   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       3.533 -12.471   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.199  -8.621   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   45                                                  
CONECT   15   14   16   44                                                  
CONECT   16   15   17   29   42                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28   22                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37   33                                                       
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   35                                                            
CONECT   42   16   43                                                       
CONECT   43   42                                                            
CONECT   44   15                                                            
CONECT   45   14                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4R)-2,3-Dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₄O₁₈

Average Mass

636.4710 Da

Monoisotopic Mass

636.09626 Da

IUPAC Name

(2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3R,4R)-2,3-dihydroxy-5-oxo-4-(3,4,5-trihydroxybenzoyloxy)-4-[(3,4,5-trihydroxybenzoyloxy)methyl]pentyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

O[C@H](COC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](O)[C@@](COC(=O)C1=CC(O)=C(O)C(O)=C1)(OC(=O)C1=CC(O)=C(O)C(O)=C1)C=O

InChI Identifier

InChI=1S/C27H24O18/c28-8-27(45-26(42)12-5-17(33)22(38)18(34)6-12,9-44-25(41)11-3-15(31)21(37)16(32)4-11)23(39)19(35)7-43-24(40)10-1-13(29)20(36)14(30)2-10/h1-6,8,19,23,29-39H,7,9H2/t19-,23-,27-/m1/s1

InChI Key

XIOBKZGXHBXTMP-AUZMWRNASA-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
Castanea crenata	Plant	KNApSAcK
Castanea sativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Beta-hydroxy aldehyde
Secondary alcohol
Carboxylic acid ester
1,2-diol
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.71	ALOGPS
logP	1.2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	318.5 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	144.93 m³·mol⁻¹	ChemAxon
Polarizability	57.07 Å³	ChemAxon
Number of Rings	3	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

103883828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154496846

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Kurigalin (NP0078543)

MOL for NP0078543 ((+)-Kurigalin)

3D MOL for NP0078543 ((+)-Kurigalin)

3D SDF for NP0078543 ((+)-Kurigalin)

3D-SDF for NP0078543 ((+)-Kurigalin)

PDB for NP0078543 ((+)-Kurigalin)

3D PDB for NP0078543 ((+)-Kurigalin)

SMILES for NP0078543 ((+)-Kurigalin)

INCHI for NP0078543 ((+)-Kurigalin)

Structure for NP0078543 ((+)-Kurigalin)

3D Structure for NP0078543 ((+)-Kurigalin)