NP-MRD: Showing NP-Card for methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate (NP0153315)

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Record Information

Version

2.0

Created at

2022-09-02 09:56:53 UTC

Updated at

2022-09-02 09:56:53 UTC

NP-MRD ID

NP0153315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate

Description

Methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]Hexadeca-3(8),4,6-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate is found in Claviceps purpurea. Methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]Hexadeca-3(8),4,6-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503032D          

 45 51  0  0  0  0            999 V2000
    6.1198    4.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494    4.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0198    3.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606    4.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1493    3.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677    3.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269    2.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269    1.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3565    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    1.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6381    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2789    2.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0493    1.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1789    1.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6901    2.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5605    3.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2014    3.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7901    3.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1642    4.2903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    0.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932   -0.3066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1228   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    0.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    1.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083    1.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3964    1.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045    0.9680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -0.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    0.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253    0.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4045    1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453    1.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157    2.3621    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
  3  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
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  2  0  0  0  0
 35 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 27 43  1  0  0  0  0
 43 44  2  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

 73 79  0  0  0  0  0  0  0  0999 V2000
   -5.7338   -3.7309    1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -2.5571    0.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8203   -1.3005    0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4540   -1.2410    1.8853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799   -0.0973    0.0259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6606   -0.5578   -1.0494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2940   -0.4830   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -1.1878   -2.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411   -1.0818   -2.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -0.2831   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8466    1.1939   -1.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6124   -2.1305    1.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2375   -1.0236    1.7418 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7162   -1.1817    1.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2699   -0.1176    0.5786 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7508    1.0943    1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3569    0.3090   -0.5083 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7474    1.5576   -0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    0.3199   -0.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0863    0.7151   -1.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6843    1.1143    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3285    2.3070    1.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    0.2630    2.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338    0.4233   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5891    1.2370    0.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967    0.2988   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3586    1.0631    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    1.7843    1.5907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8086    0.9563    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4995    1.8270    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7985    2.8166    2.2105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9831    1.8015    1.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4653    1.4867    0.1564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9663    1.1940    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7417    0.4554   -0.6079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3794    0.9218   -1.8932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8171   -3.4929    2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6674   -4.2157    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190   -4.4663    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430   -1.8133   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -1.6266   -2.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1772   -0.5639    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8702    1.1813    1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4901    0.9229    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3445    2.0468    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4567   -0.3825   -1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784    2.1725   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971    1.3463    0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4114    1.2092    2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3316    2.8685    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4112    2.4509   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4003    0.9733   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4244    2.1231    0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1637    0.3738    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  2  0
  5  3  1  1
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  8  9  1  0
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 23 56  1  0
 23 57  1  0
 22 55  1  1
 21 54  1  0
 17 53  1  0
M  END


  Mrv1533004161503032D          

 45 51  0  0  0  0            999 V2000
    6.1198    4.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494    4.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0198    3.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606    4.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1493    3.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677    3.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269    2.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269    1.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3565    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    1.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6381    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2789    2.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0493    1.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1789    1.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6901    2.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5605    3.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2014    3.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7901    3.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1642    4.2903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    0.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932   -0.3066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1228   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    0.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    1.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083    1.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3964    1.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045    0.9680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -0.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    0.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253    0.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4045    1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453    1.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157    2.3621    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
  3  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
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  2  0  0  0  0
 35 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 27 43  1  0  0  0  0
 43 44  2  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153315

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12OC3=CC=C(C(O)=C3C(=O)C1=C(O)CC(C)C2O)C1=CC=C2OC34C(O)C(C)CC(OC3=O)C4(O)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O14/c1-10-8-14(32)20-23(35)18-15(44-29(20,24(10)36)27(39)42-3)6-4-12(21(18)33)13-5-7-16-19(22(13)34)26(38)30(41)17-9-11(2)25(37)31(30,45-16)28(40)43-17/h4-7,10-11,17,24-25,32-34,36-37,41H,8-9H2,1-3H3

> <INCHI_KEY>
ZDFMCIIBGIKWCG-UHFFFAOYSA-N

> <FORMULA>
C31H28O14

> <MOLECULAR_WEIGHT>
624.551

> <EXACT_MASS>
624.147905582

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
61.128695594764395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.9198986250000005

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.408374426384638

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.438787108309414

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4931856602544133

> <JCHEM_POLAR_SURFACE_AREA>
226.57999999999998

> <JCHEM_REFRACTIVITY>
148.6764

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2H-xanthene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      11.424   9.259   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.665   7.738   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.104   7.187   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.300   8.157   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.345   5.666   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.907   6.217   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.711   5.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.273   5.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.077   4.828   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.319   3.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.757   2.756   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.999   1.235   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.953   3.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.391   3.175   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.633   1.654   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.587   4.145   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.025   3.594   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.267   2.073   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.222   4.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.980   6.085   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.176   7.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.542   6.636   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.240   8.009   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.123   2.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.364   0.816   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.168  -0.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.730   0.398   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.534  -0.572   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.096  -0.021   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.343   0.882   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.869   1.087   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.603   2.528   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.831   3.024   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.255   3.435   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.740   3.162   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.008   1.807   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.612   0.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.403  -0.768   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.854   1.499   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.421   0.937   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.050   2.469   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.808   3.990   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.488   1.918   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.685   2.888   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.443   4.409   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   16   22                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5   23                                                  
CONECT   23   22                                                            
CONECT   24   10   25   44                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   43                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37   39                                             
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   29   38                                                  
CONECT   38   37                                                            
CONECT   39   35   29   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   27   44                                                  
CONECT   44   43   24   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0,.0,]hexadeca-3(8),4,6-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylic acid	Generator
Methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3(8),4,6-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylic acid	Generator

Chemical Formula

C₃₁H₂₈O₁₄

Average Mass

624.5510 Da

Monoisotopic Mass

624.14791 Da

IUPAC Name

methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate

Traditional Name

methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2H-xanthene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12OC3=CC=C(C(O)=C3C(=O)C1=C(O)CC(C)C2O)C1=CC=C2OC34C(O)C(C)CC(OC3=O)C4(O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C31H28O14/c1-10-8-14(32)20-23(35)18-15(44-29(20,24(10)36)27(39)42-3)6-4-12(21(18)33)13-5-7-16-19(22(13)34)26(38)30(41)17-9-11(2)25(37)31(30,45-16)28(40)43-17/h4-7,10-11,17,24-25,32-34,36-37,41H,8-9H2,1-3H3

InChI Key

ZDFMCIIBGIKWCG-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
Claviceps purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Caprolactone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Monosaccharide
Benzenoid
Vinylogous acid
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Polyol
Ether
Enol
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	1.34	ALOGPS
logP	1.92	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	226.58 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.68 m³·mol⁻¹	ChemAxon
Polarizability	61.13 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate (NP0153315)

MOL for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D MOL for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D SDF for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D-SDF for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

PDB for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D PDB for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

SMILES for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

INCHI for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

Structure for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D Structure for NP0153315 (methyl 1,4,8-trihydroxy-3-methyl-9-oxo-7-{7,10,14-trihydroxy-13-methyl-9,15-dioxo-2,16-dioxatetracyclo[9.3.2.0¹,¹⁰.0³,⁸]hexadeca-3,5,7-trien-6-yl}-3,4-dihydro-2h-xanthene-4a-carboxylate)