NP-MRD: Showing NP-Card for methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0245225)

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Record Information

Version

2.0

Created at

2022-09-07 06:13:55 UTC

Updated at

2022-09-07 06:13:55 UTC

NP-MRD ID

NP0245225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Aclacinomycin X, 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-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-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 X is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514252D          

 59 65  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
    1.4289    3.3000    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
    2.8579    3.3000    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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   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
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 13 30  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  8 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 43 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 40 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 37 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

111117  0  0  0  0  0  0  0  0999 V2000
   -4.8278    4.0566   -3.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8410    3.4128   -1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5818    2.6064   -1.3879 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5378    3.5892   -1.4973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3135    1.6030   -2.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8716    0.2347   -1.9370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5395    0.3066   -1.5981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6875   -0.4119   -2.4327 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3612    0.4851   -3.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5223    0.7515   -2.1562 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7974    0.4439   -2.7227 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040   -0.8622   -3.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706    1.5079   -3.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    0.3042   -0.7550 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    0.3218    0.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608    1.1246    1.1016 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4138    2.2609    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6711    1.9448    1.8305 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8028    2.4934    1.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9330    0.5243    2.1524 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6989   -0.0465    1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8832   -0.5956    1.5584 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9511   -0.0091    0.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7398    0.0485   -0.4835 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0857    0.2967   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2110   -1.2272   -1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9132   -1.3020   -2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0688   -2.3384   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060   -2.0507    1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7651   -3.0897    2.1396 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.3147    2.2824 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7162   -1.1925    3.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.4577    2.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -0.9777   -0.5768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3713   -2.1241   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -1.4289   -1.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284   -0.2134   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0334    0.7399    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8456    0.3732    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3535   -0.8973    1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0445   -1.8447    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2329   -1.4871   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9561   -2.4614   -1.5871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5678   -3.1751    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3026   -4.0542   -0.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4078   -3.5488    1.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9139   -4.8332    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -5.7873    0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7023   -5.1717    2.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0234   -4.2343    3.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5172   -2.9532    3.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7285   -2.6045    2.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2031   -1.2454    2.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4770   -0.3794    3.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719    2.0992    0.0130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1058    3.0198    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396    3.6076    1.8349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4458    3.2718    1.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9891    4.1511    2.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8144    4.5844   -3.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593    4.8472   -3.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7731    3.3559   -3.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309    4.2550   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7404    2.7949   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    3.1410   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    1.9230   -3.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1986    1.4041   -3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733   -0.4578   -2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.8564   -3.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613    1.4390   -3.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6879    0.1077   -4.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5745    1.8995   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015   -1.1882   -2.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3138   -1.6139   -2.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -0.8619   -4.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5587    1.2221   -3.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1152    1.7506   -4.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299    2.3951   -2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460    1.0704   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249    1.5984    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    3.1899    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    2.5191    0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009    2.4934    2.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0716    3.3437    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108    0.3842    3.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0251   -0.4697    2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0997    0.9057   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8038   -0.4787   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9492    0.2293   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4713    1.3000   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0994   -3.3475   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1549   -3.9144    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2677   -3.0023    3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -1.0240    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6378   -1.8395    3.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263   -0.6493    4.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231514252D          

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 37 38  2  0  0  0  0
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 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
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 43 44  2  0  0  0  0
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 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(OC3CC(O)C(OC4OC(C)C(=O)C=C4N)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/C42H52N2O15/c1-8-42(52)16-28(32-21(34(42)40(51)53-7)12-22-33(37(32)50)36(49)31-20(35(22)48)10-9-11-25(31)45)57-29-14-24(44(5)6)38(18(3)54-29)58-30-15-27(47)39(19(4)55-30)59-41-23(43)13-26(46)17(2)56-41/h9-13,17-19,24,27-30,34,38-39,41,45,47,50,52H,8,14-16,43H2,1-7H3

> <INCHI_KEY>
OHMUKIWRHXAZQS-UHFFFAOYSA-N

> <FORMULA>
C42H52N2O15

> <MOLECULAR_WEIGHT>
824.877

> <EXACT_MASS>
824.336768982

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
86.84566915471737

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-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>
2.43

> <JCHEM_LOGP>
3.049499031876237

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.101086651624108

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.469178331977699

> <JCHEM_PKA_STRONGEST_BASIC>
8.639237532278525

> <JCHEM_POLAR_SURFACE_AREA>
243.06999999999996

> <JCHEM_REFRACTIVITY>
208.24450000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-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                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-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       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   6.160   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       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+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   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
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   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   13                                                       
CONECT   31   11   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    8                                                       
CONECT   34   10   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    6   38   54                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   52                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   49                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   43   50                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   40   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   37   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  130    0
END

View in JSmol

Synonyms

Value	Source
Aclacinomycin T	MeSH
Siwenmycin	MeSH
MA 144 S1	MeSH
Aclacinomycin m	MeSH
MA 144 N1	MeSH
Aclacinomycin hydrochloride	MeSH
Aclacinomycin	MeSH
Aclacinomycin b	MeSH
Aclacinomycin N	MeSH
Aclacinomycin y	MeSH
Aclacinomycins	MeSH
Aclacinomycin S	MeSH
Methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid	Generator

Chemical Formula

C₄₂H₅₂N₂O₁₅

Average Mass

824.8770 Da

Monoisotopic Mass

824.33677 Da

IUPAC Name

methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-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=C4N)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/C42H52N2O15/c1-8-42(52)16-28(32-21(34(42)40(51)53-7)12-22-33(37(32)50)36(49)31-20(35(22)48)10-9-11-25(31)45)57-29-14-24(44(5)6)38(18(3)54-29)58-30-15-27(47)39(19(4)55-30)59-41-23(43)13-26(46)17(2)56-41/h9-13,17-19,24,27-30,34,38-39,41,45,47,50,52H,8,14-16,43H2,1-7H3

InChI Key

OHMUKIWRHXAZQS-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
Tetracenequinone
Aminoglycoside core
Anthracene carboxylic acid or derivatives
Anthracene carboxylic acid
9,10-anthraquinone
1,4-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
1-hydroxy-4-unsubstituted benzenoid
Dihydropyranone
Pyran
Benzenoid
Oxane
Vinylogous amide
Vinylogous acid
Methyl ester
Tertiary alcohol
Tertiary aliphatic amine
Carboxylic acid ester
Cyclic ketone
Ketone
Tertiary amine
Amino acid or derivatives
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Enamine
Oxacycle
Polyol
Organic nitrogen compound
Carbonyl group
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
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	2.43	ALOGPS
logP	3.05	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	243.07 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	208.24 m³·mol⁻¹	ChemAxon
Polarizability	86.85 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

382513

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-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0245225)

MOL for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0245225 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)