NP-MRD: Showing NP-Card for Thalassiolin B (NP0086055)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 06:26:16 UTC

Updated at

2022-04-29 06:26:16 UTC

NP-MRD ID

NP0086055

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thalassiolin B

Description

[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl] hydrogen sulfate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thalassiolin B is found in Thalassia hemprichii and Thalassia testudinum. Based on a literature review very few articles have been published on [(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl] hydrogen sulfate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208262D          

 37 40  0  0  1  0            999 V2000
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  2  0  0  0  0
  9 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
 24 34  2  0  0  0  0
 34 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 22 37  2  0  0  0  0
 17 37  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    9.0031   -0.4774   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4844    0.1356   -1.5154 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1631    0.3314   -1.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532   -0.0882   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    0.1141   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -0.3232   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9829   -0.9824    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485   -1.3811    1.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244   -1.9886    2.7410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -1.0890    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690   -1.4604    2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8096   -2.1382    3.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -1.1613    1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -0.4974    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1982   -0.1650   -0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4186   -0.4334    0.6072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1460   -1.2236   -0.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4269   -0.8029   -0.5187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0636   -1.8460   -1.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -1.9511   -2.6462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4378    0.5616   -1.1913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6943    1.1483   -1.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4760    1.4811   -0.4735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3000    1.5273   -1.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0653    0.9135    0.8663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1517    0.8717    1.6877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    1.7406    3.0900 S   0  0  1  0  0  6  0  0  0  0  0  0
   -4.6602    0.7941    4.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833    2.8920    3.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5681    2.3350    3.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818   -0.1423   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770   -0.4208    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925   -0.0585   -0.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5183    0.7462   -2.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5074    1.1616   -3.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8366    0.9548   -2.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8254    1.3853   -3.8771 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2315   -1.5442   -0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9614    0.0191   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3287   -0.3648    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4054   -0.5779   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9806   -1.2179    1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133   -2.4051    3.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -1.4726    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415   -0.9863    1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952   -0.7881    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242   -1.5426   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -2.7986   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7470   -1.2801   -3.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1407    0.4585   -2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7894    1.8122   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9025    2.5119   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    2.3460   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    1.5536    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2539    1.6144    3.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149    0.3852   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    0.9200   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    1.6578   -4.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8002    1.2361   -3.6569 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 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 27 26  1  6
 27 30  1  0
 27 28  2  0
 27 29  2  0
 14 31  1  0
 31 32  2  0
 32 33  1  0
 36  3  1  0
 33  6  1  0
 32 10  1  0
 25 16  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
 34 57  1  0
 35 58  1  0
 37 59  1  0
  7 42  1  0
 12 43  1  0
 13 44  1  0
 16 45  1  1
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 23 52  1  1
 24 53  1  0
 25 54  1  1
 30 55  1  0
 31 56  1  0
M  END


  Mrv1652304292208262D          

 37 40  0  0  1  0            999 V2000
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  2  0  0  0  0
  9 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
 24 34  2  0  0  0  0
 34 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 22 37  2  0  0  0  0
 17 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086055

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OS(O)(=O)=O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O14S/c1-32-15-4-9(2-3-11(15)24)14-7-13(26)18-12(25)5-10(6-16(18)34-14)33-22-21(36-37(29,30)31)20(28)19(27)17(8-23)35-22/h2-7,17,19-25,27-28H,8H2,1H3,(H,29,30,31)/t17-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
UKJYXZRYJZSCBM-MIUGBVLSSA-N

> <FORMULA>
C22H22O14S

> <MOLECULAR_WEIGHT>
542.46

> <EXACT_MASS>
542.073026562

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
50.85660164752011

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-1.6611105843684222

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.308516132144865

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.2241482587963484

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981094004818793

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999995

> <JCHEM_REFRACTIVITY>
121.51329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <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  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -2.667  -4.620   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0      -4.207  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.127  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5   15                                                       
CONECT    9    2   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    9    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   35                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   25                                                       
CONECT   34   24   35                                                       
CONECT   35   34   21   36                                                  
CONECT   36   35                                                            
CONECT   37   22   17                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl] hydrogen sulfuric acid	Generator
[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl] hydrogen sulphate	Generator
[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl] hydrogen sulphuric acid	Generator

Chemical Formula

C₂₂H₂₂O₁₄S

Average Mass

542.4600 Da

Monoisotopic Mass

542.07303 Da

IUPAC Name

[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

Traditional Name

[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OS(O)(=O)=O)C=C2O1

InChI Identifier

InChI=1S/C22H22O14S/c1-32-15-4-9(2-3-11(15)24)14-7-13(26)18-12(25)5-10(6-16(18)34-14)33-22-21(36-37(29,30)31)20(28)19(27)17(8-23)35-22/h2-7,17,19-25,27-28H,8H2,1H3,(H,29,30,31)/t17-,19-,20+,21-,22-/m1/s1

InChI Key

UKJYXZRYJZSCBM-MIUGBVLSSA-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
Thalassia hemprichii	Plant	KNApSAcK
Thalassia testudinum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Monosaccharide
Oxane
Pyran
Vinylogous acid
Heteroaromatic compound
Organic sulfuric acid or derivatives
Secondary alcohol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.24	ALOGPS
logP	-1.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.51 m³·mol⁻¹	ChemAxon
Polarizability	50.86 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

C00056172

Chemspider ID

4591526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5493605

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Thalassiolin B (NP0086055)

MOL for NP0086055 (Thalassiolin B)

3D MOL for NP0086055 (Thalassiolin B)

3D SDF for NP0086055 (Thalassiolin B)

3D-SDF for NP0086055 (Thalassiolin B)

PDB for NP0086055 (Thalassiolin B)

3D PDB for NP0086055 (Thalassiolin B)

SMILES for NP0086055 (Thalassiolin B)

INCHI for NP0086055 (Thalassiolin B)

Structure for NP0086055 (Thalassiolin B)

3D Structure for NP0086055 (Thalassiolin B)