NP-MRD: Showing NP-Card for methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0328609)

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Record Information

Version

1.0

Created at

2022-09-12 12:14:00 UTC

Updated at

2022-09-12 12:14:00 UTC

NP-MRD ID

NP0328609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

11-Hydroxyaclacinomycin X belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces galilaeus. It was first documented in 2005 (PMID: 15918523). Based on a literature review a significant number of articles have been published on 11-Hydroxyaclacinomycin X (PMID: 18958428) (PMID: 17096162) (PMID: 16175393) (PMID: 15802811).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214142D          

 60 66  0  0  0  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  0  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  0  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  0  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  0  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  0  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
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   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    2.0625    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  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
    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    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
  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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 16 33  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  8 36  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 41 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  2  0  0  0  0
 52 58  1  0  0  0  0
 58 59  1  0  0  0  0
 40 59  1  0  0  0  0
 59 60  2  0  0  0  0
M  END

     RDKit          3D

112118  0  0  0  0  0  0  0  0999 V2000
   -2.6337   -3.9902   -3.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989   -3.8976   -2.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637   -2.5339   -2.2015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9512   -2.3572   -3.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1352   -1.4340   -2.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -0.7297   -0.7945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0795    0.1806   -0.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -0.2184   -0.0869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6312    0.7890    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970    1.1959    0.9980 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9606    2.5068    0.3936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    3.5179    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400    2.5431   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141    0.2115    0.5096 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5491   -0.3077    1.5774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -0.0803    1.3794 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3636    0.8247    2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8463    0.8394    2.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2391    2.1576    2.8773 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.1383    1.5555 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8504   -0.0200    1.8272 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6936    0.5343    0.9023 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3723   -0.5271    0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1143    0.0933   -0.7867 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6593   -0.9218   -1.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2255    0.8112   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4081    0.8126   -0.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9154    1.5470    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6760    1.4034    1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3439    2.0975    2.7613 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188   -1.2600    1.4827 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5828   -1.9892    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -1.3061    1.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -0.9594   -0.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0414   -1.8591   -0.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710   -0.5181   -0.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481   -0.2301   -0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7760    1.1039   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107    1.9443   -0.2001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118    1.4698   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1014    0.5058   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8137   -0.8331   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7852   -1.7672   -0.6420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4678   -1.1579   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519   -2.5345   -0.9871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0926   -3.5472   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4950   -4.1566   -2.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7340   -3.9236    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7422   -4.9075    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4715    0.9605   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4116    0.1358   -0.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8198    2.3679    0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1496    2.7220    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4736    4.0262    0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4843    4.9679    0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1271    4.6143    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2128    5.6092    0.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8088    3.2924    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4223    2.8692    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    3.7052    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -3.8516   -3.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -3.1745   -4.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -4.9362   -4.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2529   -4.7036   -2.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978   -4.0205   -1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5377   -1.7861   -4.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490   -1.8787   -2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248   -0.6405   -2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -1.5292   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.1824    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    1.7311    0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9191    0.3642    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127    1.3802    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7542    3.7655    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8707    4.4285    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162    3.1814    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4016    1.8048   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112    2.2453   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306    3.5742   -1.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061    0.6873   -0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.4539    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8626    0.5326    3.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0087    1.8383    2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1619    0.2887    3.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323    2.5468    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3269    0.7001    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1909    1.0720    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4820    0.8217   -1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9563   -0.9781   -2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8161   -1.8836   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6354   -0.5583   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6296    2.1834    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0437    1.6847    3.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4140    3.1569    2.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57112  1  0
M  END


  Mrv1652309122214142D          

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M  END
> <DATABASE_ID>
NP0328609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CC(OC2CC(C(OC3CC(O)C(OC4OC(C)C(=O)C=C4N)C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H52N2O16/c1-8-42(53)15-25(29-30(33(42)40(52)54-7)37(51)31-32(36(29)50)35(49)28-19(34(31)48)10-9-11-22(28)45)58-26-13-21(44(5)6)38(17(3)55-26)59-27-14-24(47)39(18(4)56-27)60-41-20(43)12-23(46)16(2)57-41/h9-12,16-18,21,24-27,33,38-39,41,45,47,50-51,53H,8,13-15,43H2,1-7H3

> <INCHI_KEY>
LPFZXQBRNYTAKP-UHFFFAOYSA-N

> <FORMULA>
C42H52N2O16

> <MOLECULAR_WEIGHT>
840.876

> <EXACT_MASS>
840.331683602

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
87.22698400576583

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
3.5178380257457817

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.653122853473617

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.163988744712952

> <JCHEM_PKA_STRONGEST_BASIC>
7.6470611544912455

> <JCHEM_POLAR_SURFACE_AREA>
263.29999999999995

> <JCHEM_REFRACTIVITY>
210.22540000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.005   6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      20.005   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      18.672   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.005  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.339  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      22.673   2.310   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   60  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   45                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29                                                            
CONECT   31   20   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   16                                                       
CONECT   34   14   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    8                                                       
CONECT   37    6   38   44                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   59                                                  
CONECT   41   40   42   50                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   37   45                                                  
CONECT   45   44    3   46                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50   41   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   58                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   52   59                                                  
CONECT   59   58   40   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid	HMDB
3'''-amino-11-hydroxyaclacinomycin y	MeSH

Chemical Formula

C₄₂H₅₂N₂O₁₆

Average Mass

840.8760 Da

Monoisotopic Mass

840.33168 Da

IUPAC Name

methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-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(OC3CC(O)C(OC4OC(C)C(=O)C=C4N)C(C)O3)C(C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C42H52N2O16/c1-8-42(53)15-25(29-30(33(42)40(52)54-7)37(51)31-32(36(29)50)35(49)28-19(34(31)48)10-9-11-22(28)45)58-26-13-21(44(5)6)38(17(3)55-26)59-27-14-24(47)39(18(4)56-27)60-41-20(43)12-23(46)16(2)57-41/h9-12,16-18,21,24-27,33,38-39,41,45,47,50-51,53H,8,13-15,43H2,1-7H3

InChI Key

LPFZXQBRNYTAKP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces galilaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Tetracenequinone
Aminoglycoside core
Anthracene carboxylic acid or derivatives
Anthracene carboxylic acid
9,10-anthraquinone
1,4-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
1-hydroxy-4-unsubstituted benzenoid
Dihydropyranone
Pyran
Benzenoid
Oxane
Vinylogous amide
Vinylogous acid
Methyl ester
Tertiary alcohol
Tertiary aliphatic amine
Carboxylic acid ester
Cyclic ketone
Ketone
Tertiary amine
Amino acid or derivatives
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Enamine
Oxacycle
Polyol
Organic nitrogen compound
Carbonyl group
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.52	ChemAxon
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	263.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	210.23 m³·mol⁻¹	ChemAxon
Polarizability	87.23 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

HMDB0244359

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

438789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shin DH, Choi KS, Park SA, Cho BS, Lee HS, Ryu JS, Kim TY, Lee CK, Song S, Chung YB: Extensive intracellular accumulation of ID-6105, a novel anthracycline, in SK-OV-3 ovarian cancer cells. Arch Pharm Res. 2008 Oct;31(10):1355-61. doi: 10.1007/s12272-001-2117-y. Epub 2008 Oct 29. [PubMed:18958428 ]
Lee HS, Ryu JS, Jeon YJ, Hong YS, Lee JJ, Hong SK, Kim TY: Apoptosis induced by ID6105, a new anthracycline (11-hydroxyaclacinomycin X, Hyrubicin), and its anti-tumor effects on experimental tumor models. Cancer Chemother Pharmacol. 2007 Jul;60(2):197-201. doi: 10.1007/s00280-006-0361-z. Epub 2006 Nov 10. [PubMed:17096162 ]
Ryu JS, Lee HS, Hong YS, Lee JJ, Sohn UD, Kim TY: In vivo antitumor efficacy and cardiotoxicity of novel anthracycline ID6105 (11-hydroxy-aclacinomycin X, Hyrubicin). Cancer Chemother Pharmacol. 2006 Jun;57(6):811-8. doi: 10.1007/s00280-005-0118-0. Epub 2005 Sep 21. [PubMed:16175393 ]
Yoo BI, Ahan KB, Kang MH, Kwon OS, Hong YS, Lee JJ, Lee HS, Ryu JS, Kim TY, Moon DC, Song S, Chung YB: Pharmacokinetics of 11-hydroxyaclacinomycin X (ID-6105), a novel anthracycline, after i.v. bolus multiple administration in rats. Arch Pharm Res. 2005 Apr;28(4):476-82. doi: 10.1007/BF02977679. [PubMed:15918523 ]
Yoo BI, Ahan KB, Kang MH, Moon DC, Kwon OS, Lee HS, Ryu JS, Kim TY, Song S, Chung YB: HPLC analysis and pharmacokinetic characteristics of 11-hydroxyaclacinomycin X (ID-6105), a novel anthracycline, in rats and beagle dogs. Biol Pharm Bull. 2005 Apr;28(4):688-93. doi: 10.1248/bpb.28.688. [PubMed:15802811 ]
LOTUS database [Link]

Showing NP-Card for methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0328609)

MOL for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0328609 (methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-2,6-dihydropyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)