NP-MRD: Showing NP-Card for methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate (NP0160167)

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Record Information

Version

2.0

Created at

2022-09-02 18:03:32 UTC

Updated at

2022-09-02 18:03:33 UTC

NP-MRD ID

NP0160167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate

Description

HIRTUSNEANOSIDE belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate is found in Usnea hirta. methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate was first documented in 2007 (PMID: 17822296). Based on a literature review very few articles have been published on HIRTUSNEANOSIDE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220032D          

 57 63  0  0  1  0            999 V2000
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -10.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026  -13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0874   -5.5201    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  2  0  0  0  0
  5  3  1  1  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 33 32  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  6  0  0  0
 30 43  1  0  0  0  0
 16 43  1  0  0  0  0
 11 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
  7 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
  5 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
  5 56  1  0  0  0  0
 56 57  1  6  0  0  0
M  END

     RDKit          3D

103109  0  0  0  0  0  0  0  0999 V2000
   -9.0459    3.7562    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3533    2.5206    0.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5713    2.0370   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4501    2.7195   -1.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8986    0.7031   -0.4530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1371    0.4082   -1.5926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7686    0.3341   -1.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159    0.1007   -2.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    0.0395   -2.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -0.2059   -4.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    0.2031   -1.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    0.1363   -1.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2603    1.2459   -1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265    2.5491   -2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6427    1.1599   -1.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954   -0.0486   -1.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -1.1549   -1.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -1.0642   -1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6326   -2.2031   -1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951   -2.3977   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384   -3.5541   -0.9922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.4908   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736   -3.7871   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235   -4.6377   -0.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689   -4.0153   -1.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -2.7629   -1.5641 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5609   -2.9875   -2.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -1.6116   -2.1265 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0137   -2.0198   -3.3687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3419   -1.2770   -1.2471 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8470   -0.9607    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227    0.0906    0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.3020    1.5298 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7094    1.5583    1.8768 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5809    2.3393    2.5740 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8155    3.4830    3.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031    1.6135    3.6879 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3747    2.4125    4.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8846    0.3012    3.1940 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1515   -0.7217    3.7920 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6116    0.1939    1.6828 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1009   -1.0051    1.1916 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   -0.1316   -1.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6567    0.4333   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    0.6027    0.6027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    0.5004   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586    0.7498    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0050    0.9011    1.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595    0.8315    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7502    0.9921    2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2204    1.6531    2.9206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0582    0.3683    2.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8676   -0.6186    3.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6583   -0.3234    1.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0618    0.2247    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8989   -0.3810   -0.2171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2169   -1.6071   -0.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3299    4.5701    0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5255    3.9237   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7961    3.7418    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7181   -0.0226   -3.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -0.8471   -4.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8193    0.7258   -4.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892   -0.7913   -3.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    3.4057   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    2.5914   -3.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    2.6215   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    2.0343   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6443   -2.1932   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.3501   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -4.3847   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0180   -4.8489   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873   -2.5219   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2597   -3.5566   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3422   -3.6251   -3.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9669   -2.0161   -2.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1108   -0.7054   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0213   -2.0346   -3.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489   -1.8793    0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339   -0.6097    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6031   -0.4277    2.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3252    2.8088    1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4988    4.2957    3.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    3.0568    4.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175    3.9300    2.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5911    1.4866    4.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3903    2.5624    5.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9353    0.1593    3.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7090   -1.4461    4.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935    1.0581    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8278   -0.8120    0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598    0.5737    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
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 19 69  1  0
M  END


  Mrv1652309022220032D          

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 28 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 33 32  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  6  0  0  0
 30 43  1  0  0  0  0
 16 43  1  0  0  0  0
 11 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
  7 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
  5 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
  5 56  1  0  0  0  0
 56 57  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0160167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12OC3=CC(C)=C(C(O)=C3C(O)=C1C(=O)[C@H](C)[C@@H](C)[C@@H]2O)C1=C(C)C=C2O[C@]3(CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@H](O)[C@H](C)CC(=O)C3=C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H46O17/c1-12-9-19-23(31(46)25-18(41)8-14(3)35(50)39(25,56-19)11-54-37-34(49)33(48)28(43)17(6)55-37)29(44)21(12)22-13(2)10-20-24(30(22)45)32(47)26-27(42)15(4)16(5)36(51)40(26,57-20)38(52)53-7/h9-10,14-17,28,33-37,43-51H,8,11H2,1-7H3/t14-,15-,16-,17+,28+,33-,34-,35-,36+,37-,39+,40-/m1/s1

> <INCHI_KEY>
TYNIMWUXFYKHJO-LSWDFQARSA-N

> <FORMULA>
C40H46O17

> <MOLECULAR_WEIGHT>
798.791

> <EXACT_MASS>
798.273500021

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
80.81597422699816

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (5S,5'R,6R,6'R,7R,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5H,5'H,6H,6'H,7H,7'H,8H,8'H,10aH,10'aH-[2,2'-bixanthene]-10a-carboxylate

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.4169593709999977

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.73118303007617

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.075269302793705

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4977949132145705

> <JCHEM_POLAR_SURFACE_AREA>
279.42999999999995

> <JCHEM_REFRACTIVITY>
197.31510000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5S,5'R,6R,6'R,7R,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5H,5'H,6H,6'H,7H,7'H-[2,2'-bixanthene]-10a-carboxylate

> <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  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      21.339 -18.480   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.005 -17.710   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.672 -18.480   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.672 -20.020   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      17.338 -20.790   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      17.338 -22.330   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.672 -23.100   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      18.672 -24.640   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      20.005 -22.330   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      21.339 -23.100   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      20.005 -20.790   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      21.339 -20.020   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       5.763 -10.304   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   49   56                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   46                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   44                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   43                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31   43                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   33   42                                                  
CONECT   42   41                                                            
CONECT   43   30   16                                                       
CONECT   44   11   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44    7   47                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47    5   50                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    5   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₄₆O₁₇

Average Mass

798.7910 Da

Monoisotopic Mass

798.27350 Da

IUPAC Name

methyl (5S,5'R,6R,6'R,7R,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5H,5'H,6H,6'H,7H,7'H,8H,8'H,10aH,10'aH-[2,2'-bixanthene]-10a-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12OC3=CC(C)=C(C(O)=C3C(O)=C1C(=O)[C@H](C)[C@@H](C)[C@@H]2O)C1=C(C)C=C2O[C@]3(CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@H](O)[C@H](C)CC(=O)C3=C(O)C2=C1O

InChI Identifier

InChI=1S/C40H46O17/c1-12-9-19-23(31(46)25-18(41)8-14(3)35(50)39(25,56-19)11-54-37-34(49)33(48)28(43)17(6)55-37)29(44)21(12)22-13(2)10-20-24(30(22)45)32(47)26-27(42)15(4)16(5)36(51)40(26,57-20)38(52)53-7/h9-10,14-17,28,33-37,43-51H,8,11H2,1-7H3/t14-,15-,16-,17+,28+,33-,34-,35-,36+,37-,39+,40-/m1/s1

InChI Key

TYNIMWUXFYKHJO-LSWDFQARSA-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
Usnea hirta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Hydroxy acid
Vinylogous acid
Methyl ester
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Enol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.37	ALOGPS
logP	1.42	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	5.08	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	279.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	197.32 m³·mol⁻¹	ChemAxon
Polarizability	80.82 Å³	ChemAxon
Number of Rings	7	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

C00039372

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

23643643

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rezanka T, Sigler K: Hirtusneanoside, an unsymmetrical dimeric tetrahydroxanthone from the lichen Usnea hirta. J Nat Prod. 2007 Sep;70(9):1487-91. doi: 10.1021/np070079m. Epub 2007 Sep 7. [PubMed:17822296 ]
LOTUS database [Link]

Showing NP-Card for methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate (NP0160167)

MOL for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

3D MOL for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

3D SDF for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

3D-SDF for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

PDB for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

3D PDB for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

SMILES for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

INCHI for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

Structure for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)

3D Structure for NP0160167 (methyl (5s,5'r,6r,6'r,7r,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-3,3',6,6',7-pentamethyl-8,8'-dioxo-10'a-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a-carboxylate)