NP-MRD: Showing NP-Card for methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0252231)

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Record Information

Version

2.0

Created at

2022-09-07 15:40:24 UTC

Updated at

2022-09-07 15:40:25 UTC

NP-MRD ID

NP0252231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-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 (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces violaceus. Based on a literature review very few articles have been published on methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217402D          

 43 47  0  0  1  0            999 V2000
    6.8104    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9979   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    5.7158   -1.6500    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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 C   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 O   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
    1.4289    0.8250    0.0000 C   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
    1.3827    4.9531    1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422    4.3740    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962    3.4076    1.0207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3027    4.1706    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834    2.3874    1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    1.0317    1.2222 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1413    1.0464    0.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    0.1777    0.2662 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2987   -0.8793   -0.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6780   -1.3348   -1.1576 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0104   -2.6284   -0.6052 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442   -2.7021    0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096   -3.1373   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505   -0.3028   -0.9971 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4948   -0.4392    0.1769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422    1.0404   -0.8948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0048    2.1875   -0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608    1.0003    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0263    0.5716    0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609   -0.7341    1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667   -1.6510    1.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7368   -1.1302    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060   -0.2058   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0721    1.1067   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    1.9919   -0.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235    1.5048    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3108    2.8834   -0.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7260    2.9650   -1.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    1.9315   -2.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670    4.0936   -2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    4.1615   -3.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -0.6155   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528    0.2170   -1.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3261   -1.9880   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5782   -2.3992   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0124   -3.6662   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2126   -4.5701    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -4.1939    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0780   -5.0444    1.3396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4350   -6.3719    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5248   -2.9067    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -2.4988    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -3.3217    1.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337    5.9807    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348    4.8757    2.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187    4.3421    1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878    5.2323   -0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    3.9021   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1536    3.6797    2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.2181    2.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    2.6907    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    0.3258    1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1287   -0.2832    1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -1.8039   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856   -0.5418   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035   -1.5272   -2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0003   -1.7688    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0245   -3.1877    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -3.4445    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -3.7265   -2.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9030   -2.3393   -1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -3.8122   -0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4139   -0.2680   -1.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4238    0.3358    0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384    1.1639   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326    2.6710   -1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215    1.7707   -0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190    2.9028   -0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460   -1.5384    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    2.9190   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    3.5358   -0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    3.8582   -3.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688    5.2251   -3.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873    3.5713   -3.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1860   -1.6643   -1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9940   -3.9972   -0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5309   -5.5725    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0777   -6.3741    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9456   -6.8168    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292   -7.0168    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
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 22 23  2  0
 23 24  1  0
 24 25  1  0
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 27 28  1  0
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 28 30  1  0
 30 31  1  0
 23 32  1  0
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 39 40  1  0
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 41 42  1  0
 42 43  2  0
 27  3  1  0
 41 34  1  0
 18  8  1  0
 26 19  1  0
 42 22  1  0
  1 44  1  0
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  1 46  1  0
  2 47  1  0
  2 48  1  0
  4 49  1  0
  5 50  1  0
  5 51  1  0
  6 52  1  1
  8 53  1  1
  9 54  1  0
  9 55  1  0
 10 56  1  6
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 12 57  1  0
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 21 69  1  0
 25 70  1  0
 27 71  1  6
 31 72  1  0
 31 73  1  0
 31 74  1  0
 35 75  1  0
 36 76  1  0
 37 77  1  0
 40 78  1  0
 40 79  1  0
 40 80  1  0
M  END


  Mrv1652309072217402D          

 43 47  0  0  1  0            999 V2000
    6.8104    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9979   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    5.7158   -1.6500    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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 C   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 O   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
    1.4289    0.8250    0.0000 C   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0252231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]1(O)C[C@H](O[C@H]2C[C@@H]([C@H](O)[C@H](C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2[C@@H]1C(=O)OC)C(=O)C1=CC=CC(OC)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H37NO11/c1-7-31(39)12-17(43-18-11-15(32(3)4)25(33)13(2)42-18)20-21(24(31)30(38)41-6)29(37)22-23(28(20)36)27(35)19-14(26(22)34)9-8-10-16(19)40-5/h8-10,13,15,17-18,24-25,33,36-37,39H,7,11-12H2,1-6H3/t13-,15-,17-,18-,24+,25+,31-/m0/s1

> <INCHI_KEY>
XSSVYBYWQBNYOH-PRRVMEHZSA-N

> <FORMULA>
C31H37NO11

> <MOLECULAR_WEIGHT>
599.633

> <EXACT_MASS>
599.236661015

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
62.40266513201058

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
2.6209258678104237

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.758698559948362

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50217539288434

> <JCHEM_PKA_STRONGEST_BASIC>
7.81383683316858

> <JCHEM_POLAR_SURFACE_AREA>
172.29

> <JCHEM_REFRACTIVITY>
153.30249999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      12.713   1.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.186   0.267   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.196  -1.447   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      12.003   8.470   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670   6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   27                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8                                                       
CONECT   19    6   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   42                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26    3   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   23   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   34   42                                                  
CONECT   42   41   22   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid	Generator

Chemical Formula

C₃₁H₃₇NO₁₁

Average Mass

599.6330 Da

Monoisotopic Mass

599.23666 Da

IUPAC Name

methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

methyl (1S,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@]1(O)C[C@H](O[C@H]2C[C@@H]([C@H](O)[C@H](C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2[C@@H]1C(=O)OC)C(=O)C1=CC=CC(OC)=C1C3=O

InChI Identifier

InChI=1S/C31H37NO11/c1-7-31(39)12-17(43-18-11-15(32(3)4)25(33)13(2)42-18)20-21(24(31)30(38)41-6)29(37)22-23(28(20)36)27(35)19-14(26(22)34)9-8-10-16(19)40-5/h8-10,13,15,17-18,24-25,33,36-37,39H,7,11-12H2,1-6H3/t13-,15-,17-,18-,24+,25+,31-/m0/s1

InChI Key

XSSVYBYWQBNYOH-PRRVMEHZSA-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 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

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
9,10-anthraquinone
1,4-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
Anisole
Amino saccharide
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Vinylogous acid
Methyl ester
Tertiary alcohol
Amino acid or derivatives
1,2-aminoalcohol
Secondary alcohol
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Ketone
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Alcohol
Amine
Organooxygen compound
Organic oxygen 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	2.62	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	172.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	153.3 m³·mol⁻¹	ChemAxon
Polarizability	62.4 Å³	ChemAxon
Number of Rings	5	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

162877114

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0252231)

MOL for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0252231 (methyl (1s,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)