NP-MRD: Showing NP-Card for (5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid (NP0287847)

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Record Information

Version

2.0

Created at

2022-09-09 17:17:31 UTC

Updated at

2022-09-09 17:17:31 UTC

NP-MRD ID

NP0287847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid

Description

Sulfemodin 8-O-beta-D-glucoside belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. (5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid is found in Rheum australe. (5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid was first documented in 2003 (PMID: 12932135). Based on a literature review very few articles have been published on Sulfemodin 8-O-beta-D-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219172D          

 35 38  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   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
    4.2868    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
    3.5724    2.0625    0.0000 O   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
    2.8579    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  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 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  1  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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 20 33  2  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -6.3699   -2.6365   -3.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0622   -2.1267   -2.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -2.9386   -2.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433   -2.4634   -2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902   -3.3103   -2.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6782   -1.1959   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775   -0.3893   -1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9847   -0.8743   -1.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6837    0.9362   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7049    1.6502   -0.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075    1.4248   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939    2.6798    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189    3.1874    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709    4.4713    1.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414    4.7519    2.9453 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.6718    5.3244    3.2375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    3.3949    3.6319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765    5.6558    3.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0122    2.3890    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271    1.0910    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470    0.3991    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325   -0.3180   -0.0099 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6483   -0.4224    1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4677   -1.5432    1.4204 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7629   -1.7264    2.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4045   -0.5952    3.4055 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6998   -1.2718    0.6133 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9838   -2.3459   -0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6325    0.0441   -0.0827 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9082    1.0565    0.8659 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280    0.3625   -0.7390 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3817   -0.0478   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676    0.6545   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -0.6802   -1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020   -1.3922   -1.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362   -2.1532   -3.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3241   -3.7156   -3.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1996   -2.4382   -2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -3.9417   -3.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631   -3.2801   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8502   -0.2102   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806    3.2849    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558    6.5741    3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9342    2.7678    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1529   -1.3448   -0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9309   -2.4263    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -1.7483    3.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3257   -2.6477    3.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4636   -0.7429    4.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5546   -1.2044    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7335   -2.1923   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149    0.0595   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6983    0.8075    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.4531   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -0.0963   -2.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6 34  1  0
 34 35  2  0
 34 33  1  0
 33 20  2  0
 20 21  1  0
 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
 20 19  1  0
 19 13  2  0
 13 14  1  0
 14 15  1  0
 15 18  1  0
 15 16  2  0
 15 17  2  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  2  0
  8  2  1  0
  7  6  1  0
 11 33  1  0
 31 22  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  5 40  1  0
 22 45  1  6
 24 46  1  6
 25 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  1
 28 51  1  0
 29 52  1  6
 30 53  1  0
 31 54  1  6
 32 55  1  0
 19 44  1  0
 18 43  1  0
 12 42  1  0
  8 41  1  0
M  END


  Mrv1652309092219172D          

 35 38  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   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
    4.2868    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
    3.5724    2.0625    0.0000 O   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
    2.8579    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  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 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  1  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
    1.4289    0.8250    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 20 33  2  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(OS(O)(=O)=O)C=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O13S/c1-7-2-9-14(11(23)3-7)18(26)15-10(16(9)24)4-8(34-35(29,30)31)5-12(15)32-21-20(28)19(27)17(25)13(6-22)33-21/h2-5,13,17,19-23,25,27-28H,6H2,1H3,(H,29,30,31)/t13-,17-,19+,20-,21-/m1/s1

> <INCHI_KEY>
YJQCYRDCKZTEMM-JNHRPPPUSA-N

> <FORMULA>
C21H20O13S

> <MOLECULAR_WEIGHT>
512.44

> <EXACT_MASS>
512.062461878

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
47.57049635768898

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-hydroxy-7-methyl-9,10-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-2-yl)oxidanesulfonic acid

> <JCHEM_LOGP>
-1.7341158521436408

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.294877339087716

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5602286658396194

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462808434

> <JCHEM_POLAR_SURFACE_AREA>
217.34999999999997

> <JCHEM_REFRACTIVITY>
114.2711

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5-hydroxy-7-methyl-9,10-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0      -1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0      -2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667   1.540   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  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   13   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   11   34                                                  
CONECT   34   33    6   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Sulfemodin 8-O-b-D-glucoside	Generator
Sulfemodin 8-O-β-D-glucoside	Generator
Sulphemodin 8-O-b-D-glucoside	Generator
Sulphemodin 8-O-beta-D-glucoside	Generator
Sulphemodin 8-O-β-D-glucoside	Generator

Chemical Formula

C₂₁H₂₀O₁₃S

Average Mass

512.4400 Da

Monoisotopic Mass

512.06246 Da

IUPAC Name

(5-hydroxy-7-methyl-9,10-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-2-yl)oxidanesulfonic acid

Traditional Name

(5-hydroxy-7-methyl-9,10-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(OS(O)(=O)=O)C=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C21H20O13S/c1-7-2-9-14(11(23)3-7)18(26)15-10(16(9)24)4-8(34-35(29,30)31)5-12(15)32-21-20(28)19(27)17(25)13(6-22)33-21/h2-5,13,17,19-23,25,27-28H,6H2,1H3,(H,29,30,31)/t13-,17-,19+,20-,21-/m1/s1

InChI Key

YJQCYRDCKZTEMM-JNHRPPPUSA-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
Rheum australe	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Arylsulfate
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Monosaccharide
Organic sulfuric acid or derivatives
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Aldehyde
Primary alcohol
Organic oxygen compound
Organooxygen 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	-1.7	ChemAxon
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	217.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.27 m³·mol⁻¹	ChemAxon
Polarizability	47.57 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	No	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

9137513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10962298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krenn L, Presser A, Pradhan R, Bahr B, Paper DH, Mayer KK, Kopp B: Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi. J Nat Prod. 2003 Aug;66(8):1107-9. doi: 10.1021/np0301442. [PubMed:12932135 ]
LOTUS database [Link]

Showing NP-Card for (5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid (NP0287847)

MOL for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

3D MOL for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

3D SDF for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

3D-SDF for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

PDB for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

3D PDB for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

SMILES for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

INCHI for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

Structure for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)

3D Structure for NP0287847 ((5-hydroxy-7-methyl-9,10-dioxo-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracen-2-yl)oxidanesulfonic acid)