NP-MRD: Showing NP-Card for methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0207518)

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Record Information

Version

2.0

Created at

2022-09-05 04:09:30 UTC

Updated at

2022-09-05 04:09:30 UTC

NP-MRD ID

NP0207518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Cinerubin belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces eurythermus. methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate was first documented in 2006 (PMID: 17015940). Based on a literature review a small amount of articles have been published on Cinerubin (PMID: 24191063) (PMID: 32807803) (PMID: 16650858).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206092D          

 58 64  0  0  0  0            999 V2000
    6.8104   -0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.6817    0.0000 C   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
    5.9979    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    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  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    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
    7.8592   -2.8875    0.0000 O   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
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   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
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    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
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
    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
    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
    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
    0.7145   -1.2375    0.0000 O   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    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  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
    4.2868    3.3000    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
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 16 31  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  8 34  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  0  0  0  0
 38 52  1  0  0  0  0
 52 53  2  0  0  0  0
 36 54  1  0  0  0  0
  3 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END

     RDKit          3D

109115  0  0  0  0  0  0  0  0999 V2000
   -5.7228    2.8600    3.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9012    3.8951    2.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9844    3.2951    1.6439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3198    4.4468    1.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394    2.3528    2.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8228    1.0298    1.5317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9057    1.1584    0.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.7762    0.8490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1143   -0.4813    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -0.4898    0.4525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5926   -0.2620    1.8284 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -1.2498    2.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9295    0.0311    2.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    0.5804   -0.4342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4565    0.0906   -1.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    0.2714   -2.1064 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9758   -1.4154   -2.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957   -1.6708   -1.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1944   -0.6280   -1.6614 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3995   -1.0160   -1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4669   -1.0524   -1.9515 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3623    0.1305   -1.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4357    0.0080   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7091   -1.2683   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6876   -1.3971    0.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8254   -2.4041   -0.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5077   -3.7309   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1279   -2.2452   -1.9051 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6289    0.5798   -0.8852 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8804    1.8828   -1.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    0.3142   -0.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    1.6707   -0.6316 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5771    3.0045   -0.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226    1.8028    0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0700    0.4757    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0639    1.3229    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668    0.7885    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5132   -0.5531    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5691   -1.4008    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743   -0.8792    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -1.7860    1.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8049   -2.8433    0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9233   -3.6323    1.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0599   -3.3744    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3339   -4.7299    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3755   -5.6068    0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5374   -5.2132   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4842   -4.3688   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2515   -2.9913   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2457   -2.2177   -1.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0426   -2.5236   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7795   -1.0868   -0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6018   -0.2395   -0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8172    2.7687    0.5373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2869    3.2200   -0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    3.7419   -0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0491    3.0756   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570    3.5018   -3.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968    2.8627    4.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8016    3.1644    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6599    1.8456    3.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1967    4.3281    3.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4711    4.7307    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    4.3468    1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209    2.0923    3.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305    2.8071    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3885    0.3968    2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    0.5652    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -0.4365   -0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223   -1.4137    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7439   -1.4823    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -1.7814    2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -2.0138    3.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578   -0.7321    3.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953    1.0448    2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -0.7688    2.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948    0.0444    3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161    1.1021    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5487    0.4238   -2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -1.4315   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.8837   -2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5236   -2.6983   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164   -1.5945   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859   -0.3487   -2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0350   -0.8999   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1601    1.0855   -2.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1193    0.8571   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0293   -2.3856    0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0460   -3.6762    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7685   -4.5513   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2323   -3.8532   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1313    0.5389    0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036    2.3321   -1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5826    1.8581   -2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052206092D          

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M  END
> <DATABASE_ID>
NP0207518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(OC3CCC(OC4OC(C)C(=O)C=C4)C(C)O3)C(C)O2)N(C)C)C2=C(C=C3C(=O)C4=C(O)C=CC(O)=C4C(=O)C3=C2O)C1C(=O)OC

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

> <INCHI_KEY>
HIMMZWQWBNOPJH-UHFFFAOYSA-N

> <FORMULA>
C42H51NO15

> <MOLECULAR_WEIGHT>
809.862

> <EXACT_MASS>
809.325869946

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
85.89311664442108

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
5.471510212963911

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.74518917919915

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.497861935315125

> <JCHEM_PKA_STRONGEST_BASIC>
8.192050172372367

> <JCHEM_POLAR_SURFACE_AREA>
217.04999999999998

> <JCHEM_REFRACTIVITY>
205.88170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.713  -0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.186   1.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.196   2.987   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   54                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   16                                                       
CONECT   32   14   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    8                                                       
CONECT   35    6   36   40                                                  
CONECT   36   35   37   54                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   52                                                  
CONECT   39   38   40   42                                                  
CONECT   40   39   35   41                                                  
CONECT   41   40                                                            
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   51                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51   38   53                                                  
CONECT   53   52                                                            
CONECT   54   36    3   55                                                  
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
Cinerubin R	MeSH
4''-Aculosyl-4'-rhodinosyl-7-rhodosaminyl-epsilon-pyrromycinone	MeSH

Chemical Formula

C₄₂H₅₁NO₁₅

Average Mass

809.8620 Da

Monoisotopic Mass

809.32587 Da

IUPAC Name

methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-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(OC3CCC(OC4OC(C)C(=O)C=C4)C(C)O3)C(C)O2)N(C)C)C2=C(C=C3C(=O)C4=C(O)C=CC(O)=C4C(=O)C3=C2O)C1C(=O)OC

InChI Identifier

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

InChI Key

HIMMZWQWBNOPJH-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 eurythermus	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
Aminoglycoside core
Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
1,4-anthraquinone
9,10-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Amino saccharide
Dihydropyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Oxane
Benzenoid
Methyl ester
Vinylogous acid
Tertiary alcohol
Amino acid or derivatives
Cyclic ketone
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aldehyde
Amine
Organooxygen 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	5.47	ChemAxon
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	8.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	217.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	205.88 m³·mol⁻¹	ChemAxon
Polarizability	85.89 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

C00016768

Chemspider ID

2339391

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3081886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kersten RD, Ziemert N, Gonzalez DJ, Duggan BM, Nizet V, Dorrestein PC, Moore BS: Glycogenomics as a mass spectrometry-guided genome-mining method for microbial glycosylated molecules. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):E4407-16. doi: 10.1073/pnas.1315492110. Epub 2013 Nov 4. [PubMed:24191063 ]
Silva LJ, Crevelin EJ, Souza DT, Lacerda-Junior GV, de Oliveira VM, Ruiz ALTG, Rosa LH, Moraes LAB, Melo IS: Actinobacteria from Antarctica as a source for anticancer discovery. Sci Rep. 2020 Aug 17;10(1):13870. doi: 10.1038/s41598-020-69786-2. [PubMed:32807803 ]
Yamazaki Y, Hasebe Y, Egawa K, Nose K, Kunimoto S, Ikeda D: Anthracyclines, small-molecule inhibitors of hypoxia-inducible factor-1 alpha activation. Biol Pharm Bull. 2006 Oct;29(10):1999-2003. doi: 10.1248/bpb.29.1999. [PubMed:17015940 ]
Beinker P, Lohkamp B, Peltonen T, Niemi J, Mantsala P, Schneider G: Crystal structures of SnoaL2 and AclR: two putative hydroxylases in the biosynthesis of aromatic polyketide antibiotics. J Mol Biol. 2006 Jun 9;359(3):728-40. doi: 10.1016/j.jmb.2006.03.060. Epub 2006 Apr 19. [PubMed:16650858 ]
LOTUS database [Link]

Showing NP-Card for methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0207518)

MOL for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0207518 (methyl 4-{[4-(dimethylamino)-6-methyl-5-({6-methyl-5-[(6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]oxan-2-yl}oxy)oxan-2-yl]oxy}-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)