NP-MRD: Showing NP-Card for (2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate (NP0289342)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 19:29:28 UTC

Updated at

2022-09-09 19:29:28 UTC

NP-MRD ID

NP0289342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate

Description

(2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl acetate 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. (2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate is found in Nocardia pseudobrasiliensis. Based on a literature review very few articles have been published on (2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092221292D          

 45 49  0  0  1  0            999 V2000
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  2  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
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7565    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   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
    5.7158   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3848   -3.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -4.4877    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 23 37  1  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
 14 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
    9.2348    1.3481    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8930    0.9610    0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1632    0.3724    1.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884    0.1323    2.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8955   -0.4578    3.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5946   -0.8084    3.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -1.4009    4.5064 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0497   -0.5764    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8487    0.0142    1.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    0.2627    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9907    0.8049   -0.8760 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.1100   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284    0.1613   -1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -0.1704   -1.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -0.7554   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -1.0425    0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -1.6286    1.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764   -0.7061    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -0.9519    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9830   -1.4845    2.9153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0667   -1.0940   -1.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8059    0.1007   -1.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108   -0.0257   -0.2107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1949    0.1654   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9780    1.2233    0.0262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3929    2.5620   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3556    1.0848   -0.3566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    1.3282   -1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2682    1.8970    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.9424    1.4990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5526   -0.2443    1.7855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5435   -0.3287    2.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2387   -1.6389    2.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620    0.6801    3.3853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816    0.7413    1.8872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9335    1.7264    2.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    0.9061    0.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394   -1.5951   -2.7264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2554   -2.1257   -3.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933   -3.4658   -3.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880   -0.4276   -3.6469 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3454   -0.9744   -5.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300    0.5058   -3.4973 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020    0.1102   -3.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.8056   -4.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8438    0.4608    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6323    1.8383   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3090    2.0842    1.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222    0.4265    3.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3287   -0.6408    4.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968   -1.5730    5.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.6263   -2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -1.9191    2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -1.8592   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.0713    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.4583   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875   -0.7785   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999    3.2695   -0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299    3.0084    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    2.4635   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8430    0.3701   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3683    2.0672   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6366    1.7535   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8100    2.5889   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043    2.5492    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0731    1.3182    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1894    1.8018    2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0950   -1.5213    3.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5583   -2.0507    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5477   -2.3538    3.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802   -0.2827    2.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098    2.6126    3.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    1.2371    3.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184    2.1603    2.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -2.3914   -2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -3.7700   -3.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -3.6882   -4.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335   -4.1094   -2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8999   -1.9288   -5.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900   -0.2415   -5.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -1.1453   -5.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010    1.4073   -3.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
 40 39  1  0
 39 38  1  0
 38 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 30 35  1  0
 35 36  1  0
 35 37  1  0
 25 27  1  6
 27 28  1  0
 27 29  1  0
 21 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  8 19  1  0
 19 20  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 14 44  1  0
 44 45  2  0
 44 41  1  0
 41 42  1  0
 41 43  1  6
 41 38  1  0
 37 23  1  0
 16 15  1  0
 18 12  1  0
  3  9  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 38 75  1  1
 21 54  1  1
 23 55  1  1
 24 56  1  0
 24 57  1  0
 26 58  1  0
 26 59  1  0
 26 60  1  0
 30 67  1  1
 33 68  1  0
 33 69  1  0
 33 70  1  0
 35 71  1  1
 36 72  1  0
 36 73  1  0
 36 74  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 13 52  1  0
  7 51  1  0
  5 50  1  0
  4 49  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
 17 53  1  0
 42 79  1  0
 42 80  1  0
 42 81  1  0
 43 82  1  0
M  END


  Mrv1652309092221292D          

 45 49  0  0  1  0            999 V2000
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  2  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
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7565    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   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
    5.7158   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3848   -3.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -4.4877    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 23 37  1  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
 14 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0289342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H](O[C@@H]2C[C@](C)([C@@H](OC(C)=O)[C@H](C)O2)N(C)C)C2=C(C=C3C(=O)C4=C(C(O)=CC=C4OC)C(=O)C3=C2O)C(=O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H37NO12/c1-13-29(44-14(2)34)31(3,33(5)6)12-19(43-13)45-27-21-16(28(39)32(4,40)30(27)42-8)11-15-20(25(21)37)26(38)22-17(35)9-10-18(41-7)23(22)24(15)36/h9-11,13,19,27,29-30,35,37,40H,12H2,1-8H3/t13-,19+,27+,29-,30+,31+,32-/m0/s1

> <INCHI_KEY>
KSIJUTXUYOOHKG-SCLGMHANSA-N

> <FORMULA>
C32H37NO12

> <MOLECULAR_WEIGHT>
627.643

> <EXACT_MASS>
627.231575635

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
63.52073306618369

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl acetate

> <JCHEM_LOGP>
2.784135623794103

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.77748647585968

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.93814727298271

> <JCHEM_PKA_STRONGEST_BASIC>
7.597475544125892

> <JCHEM_POLAR_SURFACE_AREA>
178.35999999999999

> <JCHEM_REFRACTIVITY>
158.2458

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   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  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.012   1.180   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       8.992   1.180   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      10.509   0.912   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.465   2.627   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.002  -4.620   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       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.185  -6.663   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.195  -8.377   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   44                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   38                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   30                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   23                                                       
CONECT   38   21   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   14   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,6R)-4-(Dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₃₂H₃₇NO₁₂

Average Mass

627.6430 Da

Monoisotopic Mass

627.23158 Da

IUPAC Name

(2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl acetate

Traditional Name

(2S,3R,4R,6R)-4-(dimethylamino)-2,4-dimethyl-6-{[(1R,2R,3R)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](O[C@@H]2C[C@](C)([C@@H](OC(C)=O)[C@H](C)O2)N(C)C)C2=C(C=C3C(=O)C4=C(C(O)=CC=C4OC)C(=O)C3=C2O)C(=O)[C@]1(C)O

InChI Identifier

InChI=1S/C32H37NO12/c1-13-29(44-14(2)34)31(3,33(5)6)12-19(43-13)45-27-21-16(28(39)32(4,40)30(27)42-8)11-15-20(25(21)37)26(38)22-17(35)9-10-18(41-7)23(22)24(15)36/h9-11,13,19,27,29-30,35,37,40H,12H2,1-8H3/t13-,19+,27+,29-,30+,31+,32-/m0/s1

InChI Key

KSIJUTXUYOOHKG-SCLGMHANSA-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
Nocardia pseudobrasiliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracyclinone-skeleton
Anthracycline
Tetracenequinone
Aminoglycoside core
1,4-anthraquinone
9,10-anthraquinone
Anthracene
O-glycosyl compound
Glycosyl compound
Disaccharide
Tetralin
Aryl alkyl ketone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
Alkyl aryl ether
Benzenoid
Oxane
Acyloin
Vinylogous acid
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Ketone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.78	ChemAxon
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	178.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	158.25 m³·mol⁻¹	ChemAxon
Polarizability	63.52 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

163027855

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate (NP0289342)

MOL for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

PDB for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

SMILES for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

INCHI for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

Structure for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0289342 ((2s,3r,4r,6r)-4-(dimethylamino)-2,4-dimethyl-6-{[(1r,2r,3r)-3,10,12-trihydroxy-2,7-dimethoxy-3-methyl-4,6,11-trioxo-1,2-dihydrotetracen-1-yl]oxy}oxan-3-yl acetate)