NP-MRD: Showing NP-Card for methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0210848)

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Record Information

Version

2.0

Created at

2022-09-05 08:50:58 UTC

Updated at

2022-09-05 08:50:58 UTC

NP-MRD ID

NP0210848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate 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-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces galilaeus and Streptomyces violaceus. Methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241515512D          

 59 66  0  0  0  0            999 V2000
    1.0488   -2.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -3.5692    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
    1.8612   -4.4877    0.0000 O   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    4.5375    0.0000 C   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
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    4.2868   -1.6500    0.0000 O   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
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    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  1  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 13 29  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 42 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 39 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 36 54  1  0  0  0  0
 54 55  1  0  0  0  0
  3 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
M  END

     RDKit          3D

110117  0  0  0  0  0  0  0  0999 V2000
   -3.0632   -3.7233   -3.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -2.2607   -3.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214   -1.4786   -2.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1008   -0.1179   -2.3615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -1.7680   -0.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9598   -0.4477    0.0794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0438    0.3454   -0.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.7692    0.2898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0978   -0.3333    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2398    0.3711    1.0312 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1988   -0.5008    1.5628 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975   -0.2948    3.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909   -1.9161    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8553    1.2232   -0.1034 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9762    1.8426    0.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1493    1.2831   -0.1431 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9731    0.8010    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4775    0.8846    0.6648 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0712   -0.0878    1.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2769   -0.5679    1.0413 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3565   -2.1006    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8013   -2.4275    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3854   -3.2710    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5199   -1.6117   -0.0341 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5883   -0.7530    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6337   -0.9846   -0.8596 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7681   -0.0832   -0.2685 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8235    0.2653   -1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5459    0.4854   -0.7813 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8964    1.6074   -1.6018 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4248    1.0298   -2.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8642    2.2060   -0.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    2.1481   -0.5229 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1652    3.6103   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830    1.9180   -0.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602    0.0233    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7446    0.9189    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087    1.3620    1.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0528    1.3530    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9970    0.8904    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6299    0.0223   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5136   -0.4589   -1.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -0.4069   -0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917   -1.3716   -1.9937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7437   -2.5891   -1.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3124   -2.6991   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9121   -3.6600   -2.5427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714   -4.7857   -2.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3916    1.3222    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2838    0.9278   -0.3905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8196    2.2037    1.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1335    2.5957    1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5086    3.4337    2.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5831    3.8933    3.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2659    3.4954    3.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3452    3.9707    4.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8993    2.6663    2.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5052    2.2384    2.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6873    2.6789    3.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -4.1705   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7137   -4.1156   -4.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119   -4.2408   -2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8022   -1.9836   -3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449   -1.8282   -4.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    0.4981   -2.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -2.5826   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148   -1.9707   -0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -0.7347    1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478    0.6634    1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863   -1.1884    0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471   -0.5945   -0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419    1.1079    1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.6716    3.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -1.1694    3.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.2356    3.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -2.1142    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5993   -2.2680    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6741   -2.4912    1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808    0.4653   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687    0.4031   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    1.3770    1.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7593   -0.2908    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8369    1.9024    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -0.2226    1.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7099   -2.5854    0.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0337   -2.3430    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0342   -2.4039   -0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6998   -0.8949    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4383    0.3300    0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177   -0.9976    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241515512D          

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M  END
> <DATABASE_ID>
NP0210848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(OC3CC4OC5CC(=O)C(C)OC5OC4C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H51NO16/c1-8-42(51)15-25(29-30(33(42)40(50)52-7)37(49)31-32(36(29)48)35(47)28-19(34(31)46)10-9-11-21(28)44)57-26-12-20(43(5)6)38(17(3)53-26)58-27-14-23-39(18(4)54-27)59-41-24(56-23)13-22(45)16(2)55-41/h9-11,16-18,20,23-27,33,38-39,41,44,48-49,51H,8,12-15H2,1-7H3

> <INCHI_KEY>
DKXGZTHFCJJLIP-UHFFFAOYSA-N

> <FORMULA>
C42H51NO16

> <MOLECULAR_WEIGHT>
825.861

> <EXACT_MASS>
825.320784566

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
86.9871939327283

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
4.914842563869241

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.653123637309305

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.163989006380866

> <JCHEM_PKA_STRONGEST_BASIC>
7.647061268844846

> <JCHEM_POLAR_SURFACE_AREA>
226.27999999999997

> <JCHEM_REFRACTIVITY>
203.43370000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.958  -5.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.484  -6.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.474  -8.377   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   55                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   13                                                       
CONECT   30   11   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    8                                                       
CONECT   33   10   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    6   37   54                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   51                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   48                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   42   49                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   39   52                                                  
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   36   55                                                  
CONECT   55   54    3   56                                                  
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  132    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0,]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid	Generator

Chemical Formula

C₄₂H₅₁NO₁₆

Average Mass

825.8610 Da

Monoisotopic Mass

825.32078 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC1(O)CC(OC2CC(C(OC3CC4OC5CC(=O)C(C)OC5OC4C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C42H51NO16/c1-8-42(51)15-25(29-30(33(42)40(50)52-7)37(49)31-32(36(29)48)35(47)28-19(34(31)46)10-9-11-21(28)44)57-26-12-20(43(5)6)38(17(3)53-26)58-27-14-23-39(18(4)54-27)59-41-24(56-23)13-22(45)16(2)55-41/h9-11,16-18,20,23-27,33,38-39,41,44,48-49,51H,8,12-15H2,1-7H3

InChI Key

DKXGZTHFCJJLIP-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
Streptomyces violaceus	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
Tetracenequinone
Aminoglycoside core
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
1,4-anthraquinone
9,10-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Pyranodioxin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Para-dioxane
Oxane
Vinylogous acid
Methyl ester
Tertiary alcohol
Amino acid or derivatives
Cyclic ketone
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Ketone
Monocarboxylic acid or derivatives
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Carbonyl group
Organopnictogen compound
Amine
Organic oxide
Organic nitrogen 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	2.69	ALOGPS
logP	4.91	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	226.28 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	203.43 m³·mol⁻¹	ChemAxon
Polarizability	86.99 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176066

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-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0210848)

MOL for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0210848 (methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)