NP-MRD: Showing NP-Card for (2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0149216)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 05:04:47 UTC

Updated at

2022-09-02 05:04:48 UTC

NP-MRD ID

NP0149216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

2,3,6,8-Tetrahydroxy-7-[3-O-[(E)-4-hydroxycinnamoyl]-beta-D-glucopyranosyl]-9H-xanthene-9-one belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Fridericia patellifera. Based on a literature review very few articles have been published on 2,3,6,8-Tetrahydroxy-7-[3-O-[(E)-4-hydroxycinnamoyl]-beta-D-glucopyranosyl]-9H-xanthene-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207042D          

 41 45  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    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
   -4.2868   -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
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  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  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 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
 21 33  1  0  0  0  0
 33 34  2  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
   -3.3063   -0.2229    3.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -0.2906    2.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    0.2807    1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1197    0.2518    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3443    0.7938   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3399    1.4082    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4899    1.9156   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6671    1.8094   -1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8348    2.3288   -1.9695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6944    1.2003   -2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5518    0.7005   -1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -0.8884    1.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -1.4437    1.6988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2201   -0.7826    0.9684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5253    0.5732    0.9961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9607   -1.1524    1.7841 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2605   -0.6002    1.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -0.7681    2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -1.4504    3.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946   -0.2891    1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7922    0.3921    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    0.8521    0.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2935    1.5029   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5442    1.9823   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8049    2.6784   -2.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0842    3.1367   -2.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8024    2.9073   -3.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0090    3.5980   -4.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303    2.4225   -2.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2821    1.7388   -1.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050    1.2720   -1.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435    1.5174   -2.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040    0.5802   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536    0.0923    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145    0.2858   -0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0192   -2.5073    2.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537   -3.3379    1.4434 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6115   -3.8821    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -4.7250   -0.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -2.9093    1.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1609   -3.6978    2.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937    0.7394    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3800   -0.2244   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2168    1.5003    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2664    2.4009    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9796    2.2567   -2.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8663    1.1336   -3.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148    0.2274   -2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.3643    2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -1.1327   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090    0.7203    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.6798    2.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -1.8463    3.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357   -0.4422    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3352    1.8084   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631    3.6351   -3.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2416    3.7393   -4.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    2.6064   -3.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606    0.7223   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212   -4.2725    2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911   -3.1392   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -4.5556    0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -4.9637   -1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -2.9928    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571   -3.1500    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 37  1  0
 37 36  1  0
 36 16  1  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 13 40  1  0
 40 41  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 40 37  1  0
 34 17  1  0
 11  5  1  0
 33 21  1  0
 30 23  1  0
 39 63  1  0
 38 61  1  0
 38 62  1  0
 37 60  1  1
 16 52  1  1
 14 50  1  6
 15 51  1  0
 13 49  1  1
  3 42  1  0
  4 43  1  0
  6 44  1  0
  7 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 40 64  1  6
 41 65  1  0
 19 53  1  0
 20 54  1  0
 24 55  1  0
 26 56  1  0
 28 57  1  0
 29 58  1  0
 35 59  1  0
M  END


  Mrv1652309022207042D          

 41 45  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    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
   -4.2868   -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
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  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  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 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
 21 33  1  0  0  0  0
 33 34  2  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0149216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H]1O)C1=C(O)C=C2OC3=CC(O)=C(O)C=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O13/c29-10-19-24(36)28(41-20(34)6-3-11-1-4-12(30)5-2-11)26(38)27(40-19)21-16(33)9-18-22(25(21)37)23(35)13-7-14(31)15(32)8-17(13)39-18/h1-9,19,24,26-33,36-38H,10H2/b6-3+/t19-,24-,26+,27+,28+/m1/s1

> <INCHI_KEY>
WUXMKMAPZHEERC-NZGBPCTRSA-N

> <FORMULA>
C28H24O13

> <MOLECULAR_WEIGHT>
568.487

> <EXACT_MASS>
568.121690833

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
54.687889612773496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)oxan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.368383425

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.660225612916591

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9757056708868515

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9792121002339824

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999996

> <JCHEM_REFRACTIVITY>
139.40679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   21   34                                                  
CONECT   34   33   17   35                                                  
CONECT   35   34                                                            
CONECT   36   16   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   13   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
2,3,6,8-Tetrahydroxy-7-[3-O-[(e)-4-hydroxycinnamoyl]-b-D-glucopyranosyl]-9H-xanthene-9-one	Generator
2,3,6,8-Tetrahydroxy-7-[3-O-[(e)-4-hydroxycinnamoyl]-β-D-glucopyranosyl]-9H-xanthene-9-one	Generator

Chemical Formula

C₂₈H₂₄O₁₃

Average Mass

568.4870 Da

Monoisotopic Mass

568.12169 Da

IUPAC Name

(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)oxan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H]1O)C1=C(O)C=C2OC3=CC(O)=C(O)C=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C28H24O13/c29-10-19-24(36)28(41-20(34)6-3-11-1-4-12(30)5-2-11)26(38)27(40-19)21-16(33)9-18-22(25(21)37)23(35)13-7-14(31)15(32)8-17(13)39-18/h1-9,19,24,26-33,36-38H,10H2/b6-3+/t19-,24-,26+,27+,28+/m1/s1

InChI Key

WUXMKMAPZHEERC-NZGBPCTRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Fridericia patellifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Phenolic glycoside
Xanthone
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
C-glycosyl compound
Chromone
Glycosyl compound
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Pyranone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Dialkyl ether
Ether
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Primary alcohol
Carbonyl group
Organic oxygen compound
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	2.26	ALOGPS
logP	2.37	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.98	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.41 m³·mol⁻¹	ChemAxon
Polarizability	54.69 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25156150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0149216)

MOL for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0149216 ((2r,3r,4r,5s,6s)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-4-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)