NP-MRD: Showing NP-Card for 4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid (NP0309066)

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Record Information

Version

1.0

Created at

2022-09-11 03:22:28 UTC

Updated at

2022-09-11 03:22:28 UTC

NP-MRD ID

NP0309066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid

Description

4,4'-Dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. 4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid is found in Senna alexandrina. 4,4'-Dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171508022D          

 62 69  0  0  0  0            999 V2000
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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    2.0625    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
    2.8579    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -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
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    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
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    2.1434   -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
    3.5724   -0.4125    0.0000 C   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
    1.4289    0.8250    0.0000 O   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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    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  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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  2  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 13 40  1  0  0  0  0
 34 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 12 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 44 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
  7 53  1  0  0  0  0
 11 53  2  0  0  0  0
 46 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
  5 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
  3 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END

     RDKit          3D

100107  0  0  0  0  0  0  0  0999 V2000
    2.8331    1.5969   -3.2426 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.2417   -3.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.0380   -5.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.0519   -3.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136    0.6740   -3.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7950    0.4822   -2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157    0.1047   -3.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    0.6876   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    1.0700   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558    1.2466   -1.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    1.3191    0.5642 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6805    0.5300    1.2124 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7927   -0.8709    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318   -1.6975    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824   -3.0125    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -3.8312    0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653   -3.4472    1.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3907   -5.1652    0.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787   -3.5156    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409   -2.7421   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -3.3279   -0.6497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491   -1.4079    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -0.6320    0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.0458   -0.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    0.7474    0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    1.5340    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132    0.9541    0.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6554    1.5307   -0.0930 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6416    0.9961    0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8678   -0.3489    0.4731 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9011   -0.8517    1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1417   -2.1923    1.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4720   -0.4757   -0.9158 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7127    0.2059   -0.9092 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976    0.1289   -1.9687 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5505   -0.7166   -2.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    1.4762   -1.5344 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1785    2.0524   -2.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926    2.8271    1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835    3.3015    1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9506    2.5781    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    1.2459    1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126    1.1188    1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    1.3610    2.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8151    1.2341    3.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280    0.8639    2.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0669    0.6261    1.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877    0.2630    0.8428 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3424    1.0918    1.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5909    0.7422    0.5980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5697    0.4284    1.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8170    0.0781    1.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6086   -0.2817   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.9451   -0.7339   -0.6027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6669   -1.4144   -0.2793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7229   -1.4001   -1.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9320   -1.3111    1.0077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7473   -2.0832    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011    0.7584    0.7336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9669    0.5184   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574    0.1789   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    1.1991   -5.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    0.5056   -4.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8052   -0.0798   -3.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.5720   -1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535    2.4247    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    0.4595    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633   -1.3479    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578   -5.3605   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -4.5618   -0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0455   -3.1046   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6348    2.6137    0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4949   -0.7194    2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8642   -1.6346   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200    2.1717   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785    1.3714   -2.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    3.4756    1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0043    2.9095    2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960    1.6708    3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    1.4154    4.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9178    0.7703    3.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212    0.1288    2.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.7350    1.3410    2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171508022D          

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M  END
> <DATABASE_ID>
NP0309066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=CC3=C2C(=O)C2=C(O)C=C(C=C2C3C2C3=CC=CC(OC4OC(CO)C(O)C(O)C4O)=C3C(=O)C3=C(O)C=C(C=C23)C(O)=O)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)

> <INCHI_KEY>
IPQVTOJGNYVQEO-UHFFFAOYSA-N

> <FORMULA>
C42H38O20

> <MOLECULAR_WEIGHT>
862.746

> <EXACT_MASS>
862.195643624

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
81.35560627932855

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(2-carboxy-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl)-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
1.188237431333333

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8286719029927974

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2266170035476938

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540754237026876

> <JCHEM_POLAR_SURFACE_AREA>
347.96000000000004

> <JCHEM_REFRACTIVITY>
205.44320000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(2-carboxy-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracen-9-yl)-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   61                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   57                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   53                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   53                                                  
CONECT   12   11   13   44                                                  
CONECT   13   12   14   40                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   14   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   40                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   13   34                                                  
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   12   45   50                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   44   51                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51    7   11                                                  
CONECT   54   46   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
CONECT   57    5   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59    3   62                                                  
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylate	Generator
Pursennid	MeSH
Sennoside a	MeSH
Sennoside a and b, calcium salt	MeSH
Sennoside b	MeSH
Sennoside b, calcium salt	MeSH
ND-10	MeSH
Sennoside	MeSH
Sennoside a and b	MeSH
Sennoside a, calcium salt (1:1)	MeSH
ND 10	MeSH
Sennoside a, calcium salt	MeSH
Senokot	MeSH
Sennoside a calcium and sennoside b calcium	MeSH
Sennosides sennoside b	MeSH
Sennoside a calcium	MeSH
Sennoside a+b calcium	MeSH
Sennosides sennoside a	MeSH
(9R,9's)-5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo(9,9'-bianthracene)-2,2'-dicarboxylic acid	MeSH
(9R,9R)-5,5-Bis(beta-D-glucopyranosyloxy)-9,9,10,10-tetrahydro-4,4-dihydroxy-10,10-dioxo(9,9-bianthracene)-2,2-dicarboxylic acid	MeSH
Sennoside b calcium	MeSH
Sennosides	MeSH
Sennosides a and b	MeSH
Sennosides a and b acids	MeSH

Chemical Formula

C₄₂H₃₈O₂₀

Average Mass

862.7460 Da

Monoisotopic Mass

862.19564 Da

IUPAC Name

9-(2-carboxy-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl)-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

9-(2-carboxy-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracen-9-yl)-4-hydroxy-10-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC=CC3=C2C(=O)C2=C(O)C=C(C=C2C3C2C3=CC=CC(OC4OC(CO)C(O)C(O)C4O)=C3C(=O)C3=C(O)C=C(C=C23)C(O)=O)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)

InChI Key

IPQVTOJGNYVQEO-UHFFFAOYSA-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
Senna alexandrina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
Phenolic glycoside
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
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	0.94	ALOGPS
logP	1.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	347.96 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	205.44 m³·mol⁻¹	ChemAxon
Polarizability	81.36 Å³	ChemAxon
Number of Rings	8	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

5199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid (NP0309066)

MOL for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D MOL for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D SDF for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D-SDF for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

PDB for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D PDB for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

SMILES for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

INCHI for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

Structure for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)

3D Structure for NP0309066 (4,4'-dihydroxy-10,10'-dioxo-5,5'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-9h,9'h-[9,9'-bianthracene]-2,2'-dicarboxylic acid)