NP-MRD: Showing NP-Card for methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0273632)

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Record Information

Version

2.0

Created at

2022-09-08 20:44:27 UTC

Updated at

2022-09-08 20:44:27 UTC

NP-MRD ID

NP0273632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Aclacinomycin Y1, also known as siwenmycin or ma 144 S1, 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-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces galilaeus. Aclacinomycin Y1 is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510412D          

 58 64  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
    0.0000    2.4750    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
    0.7145    3.7125    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
    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
    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
    2.1434    3.7125    0.0000 C   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
    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
    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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 17 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  2  0  0  0  0
 36 53  1  0  0  0  0
 53 54  1  0  0  0  0
  3 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END

     RDKit          3D

109115  0  0  0  0  0  0  0  0999 V2000
   -2.6324    4.7375   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4519    3.5443    0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7190    3.1364    1.4394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0644    4.3250    2.1783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494    2.1165    2.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2724    0.7158    1.8895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2315    0.6888    1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -0.0902    1.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6464   -1.0740    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812   -0.5278   -0.2107 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0075   -1.2109   -1.3980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -1.0729   -2.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -2.6207   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -0.4896    0.8530 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6271    0.4099    0.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952   -0.1295    0.1558 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8221    0.4892    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1937    0.6406    0.6184 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4147    1.8831    0.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4614   -0.4889   -0.3641 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7357   -0.3640   -0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4914   -1.4990   -0.7000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8950   -2.1597   -1.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1199   -2.0341   -2.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0616   -1.2255   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2804   -1.1591   -2.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5630   -0.4911   -0.5111 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1394    0.9162   -0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5912   -1.2258    0.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4612   -0.4213   -1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1161    0.3206   -2.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763    0.1440   -1.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -0.0668    2.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9279    0.7633    2.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    0.7825    1.8360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130    0.4141    1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3493    1.3943    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6402    1.1523    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2161   -0.0893    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4772   -1.0896    0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2006   -0.8667    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4247   -1.8009    2.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0960   -2.4101    1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4359   -3.3256    1.5994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4552   -2.6700    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0299   -3.9263    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3846   -4.9594    1.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3308   -4.0849    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0301   -3.0719   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4646   -1.8224   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1866   -1.6520   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5594   -0.3236   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2404    0.6061   -0.7038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8486    2.7964    0.5580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5170    2.8432   -0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1097    3.6796   -1.6362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890    1.9806   -1.4555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    1.9782   -2.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    4.5008   -1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976    5.4897   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    5.2758   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    2.7453    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7043    3.8343    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2290    4.6617    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    2.0314    3.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6425    2.3728    3.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9889    0.0449    2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574   -0.5571    2.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.3724   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -2.0365    0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076    0.5418   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491   -0.1047   -2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -1.0649   -3.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8307   -1.8614   -2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.9095   -0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3245   -2.8035   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503   -3.2501   -1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0940   -1.5129    0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7918   -1.2168    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8219   -0.1913    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493    1.4825    1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9251    0.5603    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462    2.6106    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -1.4628    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8719   -2.2202   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1719   -2.7438   -2.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4308   -2.5108   -3.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4057   -0.3784    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5964    1.3374    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5041    0.9914   -1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0938    1.4724   -1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2853   -1.4584   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9501   -0.2458   -3.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.5097   -3.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    1.3047   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654   -0.9270    2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937    0.1623    3.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
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 48103  1  0
 47102  1  0
M  END


  Mrv1533004251510412D          

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 33 35  1  0  0  0  0
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 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0273632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(OC3CC(O)C(OC4OC(C)C(=O)C=C4)C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H51NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-14,18-20,24,27-31,35,39-40,45-46,49,51H,8,15-17H2,1-7H3

> <INCHI_KEY>
ADCDIHNCUQOKFP-UHFFFAOYSA-N

> <FORMULA>
C42H51NO15

> <MOLECULAR_WEIGHT>
809.862

> <EXACT_MASS>
809.325869946

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
85.3855261703854

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
4.3575268419733595

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.101086651719115

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.469178332006624

> <JCHEM_PKA_STRONGEST_BASIC>
8.639237532582483

> <JCHEM_POLAR_SURFACE_AREA>
217.04999999999998

> <JCHEM_REFRACTIVITY>
204.69470000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334   8.470   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  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   6.160   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  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   58  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   54                                             
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   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19                                                       
CONECT   27   17   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   53                                                  
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                                                       
CONECT   53   52   36   54                                                  
CONECT   54   53    3   55                                                  
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
Siwenmycin	MeSH
Aclacinomycin b	MeSH
Aclacinomycin N	MeSH
Aclacinomycin S	MeSH
Aclacinomycin X	MeSH
MA 144 S1	MeSH
Aclacinomycin m	MeSH
Aclacinomycin hydrochloride	MeSH
Aclacinomycin T	MeSH
Aclacinomycin y	MeSH
Aclacinomycins	MeSH
Aclacinomycin	MeSH
MA 144 N1	MeSH

Chemical Formula

C₄₂H₅₁NO₁₅

Average Mass

809.8620 Da

Monoisotopic Mass

809.32587 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC1(O)CC(OC2CC(C(OC3CC(O)C(OC4OC(C)C(=O)C=C4)C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C42H51NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-14,18-20,24,27-31,35,39-40,45-46,49,51H,8,15-17H2,1-7H3

InChI Key

ADCDIHNCUQOKFP-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

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
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
Aryl ketone
Amino saccharide
Dihydropyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Methyl ester
Tertiary alcohol
Vinylogous acid
Amino acid or derivatives
Carboxylic acid ester
Cyclic ketone
Tertiary aliphatic amine
Ketone
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Polyol
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
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	2.7	ALOGPS
logP	4.36	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	217.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	204.69 m³·mol⁻¹	ChemAxon
Polarizability	85.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

152864

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-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0273632)

MOL for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0273632 (methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)