NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid (NP0314895)

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Record Information

Version

2.0

Created at

2022-09-11 13:15:17 UTC

Updated at

2022-09-11 13:15:17 UTC

NP-MRD ID

NP0314895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid

Description

3,4,5-Trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphen-1-yl)oxy]oxane-2-carboxylic acid belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. Based on a literature review very few articles have been published on 3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphen-1-yl)oxy]oxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215152D          

 36 40  0  0  0  0            999 V2000
    2.9366    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0675   -3.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1476   -3.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4177   -4.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -4.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0675   -5.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -4.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -4.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.9164    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  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
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  0  0  0  0
 19 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    5.8026   -1.0434   -4.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569   -0.5808   -3.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116   -0.7925   -3.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0868   -1.4512   -4.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -1.6477   -4.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -1.1948   -2.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -0.5363   -2.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.3359   -2.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725    0.3553   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038    0.5640   -1.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190    0.8415    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814    1.4976    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065    1.9600    2.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1599    1.7790    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096    2.2588    3.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    2.0952    3.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2986    2.6171    5.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979    1.4495    2.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183    0.9407    1.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    0.3171    0.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    0.0690    0.9306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3671   -1.3354    0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -1.7134    1.2354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7358   -3.1909    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6981   -3.8635    0.9791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8834   -3.9155    1.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625   -1.1922    0.2372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6455   -0.4320    0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678   -0.3551   -0.8152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8787    0.2593   -1.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489    0.6805   -0.1663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7903    1.7477    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    1.1128    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399    0.6374    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1659   -0.0528   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.2853   -0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8893   -2.1598   -4.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8112   -0.5903   -4.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -0.7752   -5.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.8399   -5.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1541   -2.1648   -4.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -1.3575   -2.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1295    1.6350    0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    2.4862    2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512    2.7669    4.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    3.6696    5.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560    1.9994    5.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    2.6537    4.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5475    1.3062    3.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    0.4210    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9745   -1.3926    2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3346   -4.4117    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1972   -2.0022   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4120   -0.3659    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3340   -1.0329   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496    1.2146   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4460    1.1070   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    1.5696    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
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  7  8  2  0
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 16 18  1  0
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 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 19 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
  8  3  1  0
 34 11  1  0
 35  7  1  0
 33 14  1  0
 31 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  5 41  1  0
  6 42  1  0
 12 43  1  0
 13 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  1
 23 51  1  1
 27 53  1  6
 28 54  1  0
 29 55  1  6
 30 56  1  0
 31 57  1  6
 32 58  1  0
 26 52  1  0
M  END


  Mrv1652309112215152D          

 36 40  0  0  0  0            999 V2000
    2.9366    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0675   -3.0077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1476   -3.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4177   -4.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -4.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0675   -5.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -4.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -4.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.9164    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
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 12 13  1  0  0  0  0
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 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  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
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  0  0  0  0
 19 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0314895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1C(=O)C1=CC=C3C=C(C)C=C(OC4OC(C(O)C(O)C4O)C(O)=O)C3=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O10/c1-10-8-11-6-7-13-18(20(28)12-4-3-5-14(34-2)17(12)19(13)27)16(11)15(9-10)35-26-23(31)21(29)22(30)24(36-26)25(32)33/h3-9,21-24,26,29-31H,1-2H3,(H,32,33)

> <INCHI_KEY>
AMWRMWBDZWNIIN-UHFFFAOYSA-N

> <FORMULA>
C26H22O10

> <MOLECULAR_WEIGHT>
494.452

> <EXACT_MASS>
494.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.76718714002085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphen-1-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_LOGP>
2.012574077999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.21679090227037

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.16843819287678

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868270372675713

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
123.0983

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.482   1.661   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.514   2.243   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.043  -3.868   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.547  -5.323   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.059  -5.614   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.563  -7.070   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.076  -7.361   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.084  -6.197   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      17.580  -8.816   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.555  -8.234   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.059  -9.689   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.043  -7.943   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.035  -9.107   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.539  -6.488   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.027  -6.197   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   21   32                                                  
CONECT   32   31                                                            
CONECT   33   19   14   34                                                  
CONECT   34   33   11   35                                                  
CONECT   35   34    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphen-1-yl)oxy]oxane-2-carboxylate	Generator

Chemical Formula

C₂₆H₂₂O₁₀

Average Mass

494.4520 Da

Monoisotopic Mass

494.12130 Da

IUPAC Name

3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphen-1-yl)oxy]oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(=O)C1=CC=C3C=C(C)C=C(OC4OC(C(O)C(O)C4O)C(O)=O)C3=C1C2=O

InChI Identifier

InChI=1S/C26H22O10/c1-10-8-11-6-7-13-18(20(28)12-4-3-5-14(34-2)17(12)19(13)27)16(11)15(9-10)35-26-23(31)21(29)22(30)24(36-26)25(32)33/h3-9,21-24,26,29-31H,1-2H3,(H,32,33)

InChI Key

AMWRMWBDZWNIIN-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Anthracene
1-o-glucuronide
Phenanthrene
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Anisole
Aryl ketone
Alkyl aryl ether
Beta-hydroxy acid
Benzenoid
Pyran
Hydroxy acid
Monosaccharide
Oxane
Ketone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aldehyde
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	2.01	ChemAxon
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.1 m³·mol⁻¹	ChemAxon
Polarizability	47.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78074352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid (NP0314895)

MOL for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

3D MOL for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

3D SDF for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

3D-SDF for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

PDB for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

3D PDB for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

SMILES for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

INCHI for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

Structure for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)

3D Structure for NP0314895 (3,4,5-trihydroxy-6-[(8-methoxy-3-methyl-7,12-dioxotetraphen-1-yl)oxy]oxane-2-carboxylic acid)