NP-MRD: Showing NP-Card for Sibiricose A6 (NP0078748)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 23:49:09 UTC

Updated at

2022-04-28 23:49:09 UTC

NP-MRD ID

NP0078748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sibiricose A6

Description

Sibiricose A6 belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Sibiricose A6 is found in Polygala arillata, Polygala karensium, Polygala sibirica , Polygala tricornis and Raphanus sativus. Sibiricose A6 was first documented in 2004 (PMID: 15506285). Based on a literature review a significant number of articles have been published on Sibiricose A6 (PMID: 29017076) (PMID: 28342292) (PMID: 29261155) (PMID: 32956609) (PMID: 31354847) (PMID: 30340065).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201492D          

 38 40  0  0  1  0            999 V2000
   -2.0197   -1.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -0.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9759    0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -0.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9320    1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3736   -0.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306   -1.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8152   -1.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2351   -1.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636   -2.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -2.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074   -3.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341   -1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187   -2.0372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7862   -1.5523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -2.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -2.8218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3737   -2.8218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8888   -3.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836   -3.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -4.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812   -0.8335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011   -0.1234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3961    0.5953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8161    1.3055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6411    1.2968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0461    0.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6261   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8710    0.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760   -0.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610    2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4111    2.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5712    0.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912   -0.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -0.8249    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 20 23  1  6  0  0  0
 23 24  1  0  0  0  0
 18 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 28 35  1  1  0  0  0
 27 36  1  6  0  0  0
 18 37  1  1  0  0  0
 37 38  1  0  0  0  0
M  END

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
    7.1390    1.4437    3.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0013    0.1171    2.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084   -0.3374    1.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236    0.4824    1.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233    0.0349    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152    0.9336    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299    0.6002    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4822    1.6068   -0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302    2.7774    0.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882    1.3287   -0.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110    2.2254   -1.1383 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9478    2.3534   -2.6538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9559    3.1062   -3.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861    3.0509   -2.6171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0534    2.8608   -3.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2724    3.3469   -4.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9590    2.6070   -1.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862    1.8394   -0.7182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3594    2.3068    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    3.6717    0.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577    0.5461   -0.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7879   -0.4411   -0.2647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7083   -1.2137    0.5087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9972   -1.9768    1.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6204   -1.1574    2.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -0.6697    3.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -2.5144    0.8321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4552   -3.7439    1.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -2.7149   -0.6517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5322   -2.9701   -1.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -1.4450   -1.3106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4651   -1.7987   -2.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352   -1.2846    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112   -2.1228    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7981   -3.4465    0.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7669   -4.0595   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954   -1.6536    1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9611   -2.5127    1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1797    1.7006    3.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5021    1.6697    3.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8181    2.1445    2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8783    1.5064    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    1.9729    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4148   -0.3900   -0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234    3.2477   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220    1.3230   -3.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472    2.4941   -3.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0577    4.1432   -2.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9748    3.4743   -3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    1.8008   -4.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    4.3287   -4.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4401    2.1874    0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691    1.7387    1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906    3.8480    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812   -0.0738    0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -2.7973    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.8763    3.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -0.3852    2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5634   -1.0407    2.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945   -1.8027    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -4.2438    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257   -3.6044   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -3.8387   -1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.0002   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368   -0.9883   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9090   -1.7059    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -3.3744   -1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736   -5.0072   -0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -4.4055    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7778   -2.2220    2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  5 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 37  3  1  0
 18 11  1  0
 31 22  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  6 43  1  0
  7 44  1  0
 11 45  1  1
 12 46  1  6
 13 47  1  0
 14 48  1  1
 15 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 22 55  1  1
 24 56  1  1
 25 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  6
 28 61  1  0
 29 62  1  1
 30 63  1  0
 31 64  1  6
 32 65  1  0
 33 66  1  0
 36 67  1  0
 36 68  1  0
 36 69  1  0
 38 70  1  0
M  END


  Mrv1652304292201492D          

 38 40  0  0  1  0            999 V2000
   -2.0197   -1.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -0.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9759    0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -0.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9320    1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3736   -0.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306   -1.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8152   -1.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2351   -1.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636   -2.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -2.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074   -3.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341   -1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187   -2.0372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7862   -1.5523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -2.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -2.8218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3737   -2.8218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8888   -3.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836   -3.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -4.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812   -0.8335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011   -0.1234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3961    0.5953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8161    1.3055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6411    1.2968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0461    0.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6261   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8710    0.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760   -0.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610    2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4111    2.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5712    0.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912   -0.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -0.8249    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 20 23  1  6  0  0  0
 23 24  1  0  0  0  0
 18 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 28 35  1  1  0  0  0
 27 36  1  6  0  0  0
 18 37  1  1  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@H]2[C@H](O)[C@@H](CO)O[C@@]2(CO)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O15/c1-33-11-5-10(6-12(34-2)16(11)28)3-4-15(27)36-21-18(30)14(8-25)37-23(21,9-26)38-22-20(32)19(31)17(29)13(7-24)35-22/h3-6,13-14,17-22,24-26,28-32H,7-9H2,1-2H3/b4-3+/t13-,14-,17-,18-,19+,20-,21+,22-,23+/m1/s1

> <INCHI_KEY>
WTCVROXOIQEIRC-IBVGEFGBSA-N

> <FORMULA>
C23H32O15

> <MOLECULAR_WEIGHT>
548.494

> <EXACT_MASS>
548.17412033

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.358896241121826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-1.20

> <JCHEM_LOGP>
-2.1138520986666673

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.113035801403182

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.28803945830687

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849128024337

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
123.24909999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <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      -3.770  -1.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.915  -2.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.379  -2.454   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.699  -0.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.555   0.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.090  -0.393   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.875   1.589   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.340   2.065   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.164  -0.472   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.524  -3.484   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.988  -3.008   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.306  -2.375   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.985  -3.881   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.521  -4.357   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.201  -5.864   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.624  -3.327   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.088  -3.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.334  -2.898   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.580  -3.803   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.104  -5.267   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.564  -5.267   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.659  -6.513   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.009  -6.513   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.383  -7.920   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.578  -1.556   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.362  -0.230   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.606   1.111   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.390   2.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.930   2.421   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.686   1.079   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.902  -0.246   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.226   1.063   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.982  -0.279   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.714   3.746   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.634   3.779   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.066   1.127   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.090  -1.556   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.630  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   25   37                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
CONECT   25   18   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
CONECT   37   18   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
3'-Sinapoyl sucrose	MeSH
3'-Sinapoylsucrose	MeSH

Chemical Formula

C₂₃H₃₂O₁₅

Average Mass

548.4940 Da

Monoisotopic Mass

548.17412 Da

IUPAC Name

(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Traditional Name

(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2[C@H](O)[C@@H](CO)O[C@@]2(CO)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C23H32O15/c1-33-11-5-10(6-12(34-2)16(11)28)3-4-15(27)36-21-18(30)14(8-25)37-23(21,9-26)38-22-20(32)19(31)17(29)13(7-24)35-22/h3-6,13-14,17-22,24-26,28-32H,7-9H2,1-2H3/b4-3+/t13-,14-,17-,18-,19+,20-,21+,22-,23+/m1/s1

InChI Key

WTCVROXOIQEIRC-IBVGEFGBSA-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
Polygala arillata	Plant	KNApSAcK
Polygala karensium	LOTUS Database	35616633
Polygala sibirica	Plant	KNApSAcK
Polygala tricornis	Plant	KNApSAcK
Raphanus sativus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Ketal
Fatty acid ester
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Ether
Organoheterocyclic compound
Polyol
Primary alcohol
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.2	ALOGPS
logP	-2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.25 m³·mol⁻¹	ChemAxon
Polarizability	52.36 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

C00042997

Chemspider ID

4885194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6326021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang C, Yin X, Dong X, Zhang X, You L, Wang W, Wang J, Chen Q, Ni J: Determination of the phytochemical composition of Jingning fang and the in vivo pharmacokinetics of its metabolites in rat plasma by UPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Nov 1;1067:71-88. doi: 10.1016/j.jchromb.2017.09.019. Epub 2017 Sep 21. [PubMed:29017076 ]
Wang X, Zhang Y, Niu H, Geng Y, Wang B, Yang X, Yan P, Li Q, Bi K: Ultra-fast liquid chromatography with tandem mass spectrometry determination of eight bioactive components of Kai-Xin-San in rat plasma and its application to a comparative pharmacokinetic study in normal and Alzheimer's disease rats. J Sep Sci. 2017 May;40(10):2131-2140. doi: 10.1002/jssc.201601343. Epub 2017 Apr 19. [PubMed:28342292 ]
Xu R, Mao F, Zhao Y, Wang W, Fan L, Gao X, Zhao J, Tian H: UPLC Quantitative Analysis of Multi-Components by Single Marker and Quality Evaluation of Polygala tenuifolia Wild. Extracts. Molecules. 2017 Dec 20;22(12). pii: molecules22122276. doi: 10.3390/molecules22122276. [PubMed:29261155 ]
Zhao X, Xu B, Wu P, Zhao P, Guo C, Cui Y, Zhang Y, Zhang X, Li H: UHPLC-MS/MS method for pharmacokinetic and bioavailability determination of five bioactive components in raw and various processed products of Polygala tenuifolia in rat plasma. Pharm Biol. 2020 Dec;58(1):969-978. doi: 10.1080/13880209.2020.1818790. [PubMed:32956609 ]
Ba Y, Wang M, Zhang K, Chen Q, Wang J, Lv H, Jiang Y, Shi R: Intestinal Absorption Profile of Three Polygala Oligosaccharide Esters in Polygalae Radix and the Effects of Other Components in Polygalae Radix on Their Absorption. Evid Based Complement Alternat Med. 2019 Jul 2;2019:1379531. doi: 10.1155/2019/1379531. eCollection 2019. [PubMed:31354847 ]
Xu B, Qu C, Zheng W, Xi Y, Zhao X, Li H, Liu J, Zhang X: UHPLC-MS/MS method for simultaneous determination of Radix Polygalae glycolipids and organic acids in rat plasma and application in a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Nov 15;1100-1101:165-173. doi: 10.1016/j.jchromb.2018.09.037. Epub 2018 Oct 2. [PubMed:30340065 ]
Shi Q, Chen J, Zhou Q, Lei H, Luan L, Liu X, Wu Y: Indirect identification of antioxidants in Polygalae Radix through their reaction with 2,2-diphenyl-1-picrylhydrazyl and subsequent HPLC-ESI-Q-TOF-MS/MS. Talanta. 2015 Nov 1;144:830-5. doi: 10.1016/j.talanta.2015.07.032. Epub 2015 Jul 11. [PubMed:26452897 ]
Tu HH, Liu P, Mu L, Liao HB, Xie TT, Ma LH, Liu YM: [Study on antidepressant components of sucrose ester from Polygala tenuifolia]. Zhongguo Zhong Yao Za Zhi. 2008 Jun;33(11):1278-80. [PubMed:18831206 ]
Yong J, Tu PF: [Studies on the chemical constituents in root bark of Polygala tenuifolia (II)]. Zhongguo Zhong Yao Za Zhi. 2004 Aug;29(8):751-3. [PubMed:15506285 ]

Showing NP-Card for Sibiricose A6 (NP0078748)

MOL for NP0078748 (Sibiricose A6)

3D MOL for NP0078748 (Sibiricose A6)

3D SDF for NP0078748 (Sibiricose A6)

3D-SDF for NP0078748 (Sibiricose A6)

PDB for NP0078748 (Sibiricose A6)

3D PDB for NP0078748 (Sibiricose A6)

SMILES for NP0078748 (Sibiricose A6)

INCHI for NP0078748 (Sibiricose A6)

Structure for NP0078748 (Sibiricose A6)

3D Structure for NP0078748 (Sibiricose A6)