NP-MRD: Showing NP-Card for methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0167440)

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Record Information

Version

2.0

Created at

2022-09-03 03:01:19 UTC

Updated at

2022-09-03 03:01:19 UTC

NP-MRD ID

NP0167440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Auramycin D belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces galilaeus. Auramycin D is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261516512D          

 40 44  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -2.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -2.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  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
  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  2  0  0  0  0
  7  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  1  0  0  0  0
 15 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 30 37  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
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   -1.6295    4.6271   -0.7067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    3.2760   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7383    2.9084    0.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316    2.2847   -1.5787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1995    0.9559   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313    0.5585   -0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8519   -0.6937   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -1.5763   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033   -1.2163   -0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4933   -2.0519    0.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214    0.0675   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    0.4855   -0.8317 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0640   -0.5066   -0.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857   -0.1579    0.4441 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3739   -0.0230   -0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -1.0645    0.3809 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6834   -0.7935    0.0407 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8454   -0.8234   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9209   -0.8734    2.4341 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0528    0.4982    3.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -0.9902    1.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    1.1492   -2.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6026    2.2825   -2.3791 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1223    3.6289   -2.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656    2.2319   -3.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -2.9014    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3121   -3.6882    0.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6395   -3.2816    0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003   -4.5109    1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0995   -5.4466    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3739   -4.7965    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3498   -3.9173    0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9529   -2.6976    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6241   -2.3768    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2542   -1.0542   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1508   -0.2203   -0.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2863    6.4508    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    6.1196    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512    5.2289    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7234    2.6613   -2.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695    1.2908   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3351   -2.9203    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.3169   -0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.8666    0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    1.0165   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2784   -0.1938   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0539   -2.0351   -0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6909    0.2035   -1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.0806   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1825   -1.5842   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0505    0.2644    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6406    1.0648   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4663    1.0817    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358   -2.4257    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -1.2882    3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6609   -1.5662    3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995    0.8532    3.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707    1.2593    2.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    0.4001    3.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3781    1.5789   -2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    0.3916   -2.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279    4.4728   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    3.5498   -2.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    3.8360   -1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    3.1586   -4.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507   -5.4623    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389   -5.7751    1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4091   -4.1586    0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6933   -1.9752   -0.0643 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  9 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 27  5  1  0
 25 15  1  0
 38 32  1  0
 12  6  1  0
 39  8  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  6
  7 45  1  0
 11 46  1  0
 13 47  1  1
 26 64  1  0
 26 65  1  0
 28 66  1  0
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 28 68  1  0
 29 69  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 17 51  1  6
 21 58  1  6
 22 59  1  0
 23 60  1  1
 24 61  1  0
 24 62  1  0
 24 63  1  0
 19 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 20 57  1  0
 34 70  1  0
 35 71  1  0
 36 72  1  0
 37 73  1  0
M  END


  Mrv1533004261516512D          

 40 44  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -2.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -2.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  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
  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  2  0  0  0  0
  7  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  1  0  0  0  0
 15 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 30 37  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2=CC3=C(C(O)=C2C(CC1(C)O)OC1CC(C(O)C(C)O1)N(C)C)C(=O)C1=C(O)C=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H33NO10/c1-12-24(32)16(30(3)4)10-19(39-12)40-18-11-29(2,37)23(28(36)38-5)14-9-15-22(27(35)21(14)18)26(34)20-13(25(15)33)7-6-8-17(20)31/h6-9,12,16,18-19,23-24,31-32,35,37H,10-11H2,1-5H3

> <INCHI_KEY>
QJXJRECTYIMQFD-UHFFFAOYSA-N

> <FORMULA>
C29H33NO10

> <MOLECULAR_WEIGHT>
555.58

> <EXACT_MASS>
555.210446267

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.489364673145246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
1.9560800818882154

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.12018052372975

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.476068714285821

> <JCHEM_PKA_STRONGEST_BASIC>
8.666111390833397

> <JCHEM_POLAR_SURFACE_AREA>
163.06

> <JCHEM_REFRACTIVITY>
142.31529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.462  -5.336   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.185  -4.084   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0       2.667 -13.860   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
CONECT   38   32   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid	Generator

Chemical Formula

C₂₉H₃₃NO₁₀

Average Mass

555.5800 Da

Monoisotopic Mass

555.21045 Da

IUPAC Name

methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2=CC3=C(C(O)=C2C(CC1(C)O)OC1CC(C(O)C(C)O1)N(C)C)C(=O)C1=C(O)C=CC=C1C3=O

InChI Identifier

InChI=1S/C29H33NO10/c1-12-24(32)16(30(3)4)10-19(39-12)40-18-11-29(2,37)23(28(36)38-5)14-9-15-22(27(35)21(14)18)26(34)20-13(25(15)33)7-6-8-17(20)31/h6-9,12,16,18-19,23-24,31-32,35,37H,10-11H2,1-5H3

InChI Key

QJXJRECTYIMQFD-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
Streptomyces galilaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracyclinone-skeleton
Anthracycline
Aminoglycoside core
Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
1,4-anthraquinone
9,10-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Amino saccharide
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monosaccharide
Oxane
Tertiary alcohol
Methyl ester
Vinylogous acid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Ketone
1,2-aminoalcohol
Carboxylic acid ester
Amino acid or derivatives
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	1.96	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.32 m³·mol⁻¹	ChemAxon
Polarizability	58.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

174252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0167440)

MOL for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0167440 (methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-2-methyl-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)