NP-MRD: Showing NP-Card for (8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione (NP0259986)

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Record Information

Version

2.0

Created at

2022-09-08 02:01:28 UTC

Updated at

2022-09-08 02:01:29 UTC

NP-MRD ID

NP0259986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione

Description

Trisarubicinol 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. (8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione is found in Streptomyces galilaeus. (8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione was first documented in 1981 (PMID: 7319909). Based on a literature review very few articles have been published on Trisarubicinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204012D          

 56 62  0  0  1  0            999 V2000
    5.4676    2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104    1.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5282    0.6817    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  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  2  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  1  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  2  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  2  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  1  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  2  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  2  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  2  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
    5.7158   -0.0000    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
    0.7145   -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
    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
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 31 38  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 25 41  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 17 44  1  0  0  0  0
 15 45  1  0  0  0  0
  4 45  1  0  0  0  0
 11 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 48 54  1  0  0  0  0
 54 55  1  0  0  0  0
 10 55  1  0  0  0  0
 55 56  2  0  0  0  0
M  END

     RDKit          3D

107113  0  0  0  0  0  0  0  0999 V2000
   10.1614   -1.6441    2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9163   -0.1582    1.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5876    0.1293    1.6841 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1322   -0.2387    0.4038 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7783    0.1581    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8998   -0.8799    0.2238 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9983   -1.0795    1.4344 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6754   -1.0805    2.6272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -0.0352    1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.1547    0.2120 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3282   -0.8649   -0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -0.4564   -0.3853 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7830   -0.6266   -1.8694 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822    0.5998   -2.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -0.8699   -2.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230   -0.6920   -1.2819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7089   -0.6417   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3582    0.5049   -1.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6670    1.3661   -2.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493    2.5719   -2.3069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7376    2.4488   -2.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7443    3.7679   -2.9517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6507    3.5123   -4.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    3.9257   -2.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5354    2.7652   -0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2037    1.5794   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    1.5749    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9533    2.7182    0.8821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8766    0.3660    0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2822   -0.8169    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1141   -0.8137   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6150   -2.0543   -0.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727    0.3598   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313   -2.1095    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2715   -3.1633    0.6912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0517   -2.1405    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5784   -3.3569    2.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0579   -4.5768    1.9837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7399   -3.3455    3.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2954   -2.1343    3.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7791   -0.9439    2.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6391   -0.9278    2.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0685    0.3402    1.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6214    1.4036    2.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1210   -1.7969   -0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -1.2617    0.4835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5025   -0.5563    1.5888 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3890    0.0870    2.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802   -1.5128    2.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1382    0.4134   -0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9988   -0.6601   -0.9515 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8365   -0.3926   -2.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9021    0.4536   -0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3852    0.3274   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7772    0.4701    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7672    1.0770    1.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2438   -1.8156    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7654   -2.2355    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1667    0.2688    2.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2195   -1.3247    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4587   -1.8163    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.0623    1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5740   -1.5103    2.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530    0.9741    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2297   -0.3307    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    1.1450    0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905    0.6483   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -1.4971   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097    0.3701   -3.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    1.4732   -1.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441    0.9373   -3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    0.2797   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6414    1.1221   -0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2298    0.7856   -3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    1.6445   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    1.8194   -3.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2991    4.6930   -2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264    4.2510   -5.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9790    2.5156   -4.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931    4.8246   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0488    3.7288   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4707    2.8907   -0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6234    3.6193    0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8506   -2.3189   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1739   -4.2734    3.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1880   -2.1285    4.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2190    0.0232    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -2.7154   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407   -2.0882    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -2.1610    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082204012D          

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  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
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 10 11  2  0  0  0  0
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 48 54  1  0  0  0  0
 54 55  1  0  0  0  0
 10 55  1  0  0  0  0
 55 56  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0259986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)[C@@]1(O)CC(O[C@H]2C[C@@H](C(O[C@H]3C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O3)[C@H](C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1)C(=O)C1=CC=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H51NO15/c1-16-23(43)10-11-27(51-16)55-39-18(3)53-29(13-25(39)45)56-38-17(2)52-28(12-22(38)41(5)6)54-26-15-40(50,19(4)42)14-21-31(26)37(49)33-32(35(21)47)34(46)20-8-7-9-24(44)30(20)36(33)48/h7-9,16-19,22,25-29,38-39,42,44-45,47,49-50H,10-15H2,1-6H3/t16-,17-,18-,19?,22-,25-,26?,27-,28-,29-,38?,39+,40-/m0/s1

> <INCHI_KEY>
RFRIIINGCQOYCL-QCPFSNFXSA-N

> <FORMULA>
C40H51NO15

> <MOLECULAR_WEIGHT>
785.84

> <EXACT_MASS>
785.325869946

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
81.45475137275008

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S)-10-{[(2R,4S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <JCHEM_LOGP>
3.8704402705326566

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.259693175086227

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.765192974768339

> <JCHEM_PKA_STRONGEST_BASIC>
10.141322826134212

> <JCHEM_POLAR_SURFACE_AREA>
231.20999999999995

> <JCHEM_REFRACTIVITY>
196.43019999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8S)-10-{[(2R,4S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7H-tetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.206   4.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.196   2.987   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.713   3.255   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.186   1.273   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   45                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   55                                                  
CONECT   11   10   12   46                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16   45                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   44                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24   42                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   41                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31                                                       
CONECT   39   29   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   25                                                       
CONECT   42   23   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   17                                                       
CONECT   45   15    4                                                       
CONECT   46   11   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   54                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   48   55                                                  
CONECT   55   54   10   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₁NO₁₅

Average Mass

785.8400 Da

Monoisotopic Mass

785.32587 Da

IUPAC Name

(8S)-10-{[(2R,4S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(O)[C@@]1(O)CC(O[C@H]2C[C@@H](C(O[C@H]3C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O3)[C@H](C)O2)N(C)C)C2=C(O)C3=C(C(O)=C2C1)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C40H51NO15/c1-16-23(43)10-11-27(51-16)55-39-18(3)53-29(13-25(39)45)56-38-17(2)52-28(12-22(38)41(5)6)54-26-15-40(50,19(4)42)14-21-31(26)37(49)33-32(35(21)47)34(46)20-8-7-9-24(44)30(20)36(33)48/h7-9,16-19,22,25-29,38-39,42,44-45,47,49-50H,10-15H2,1-6H3/t16-,17-,18-,19?,22-,25-,26?,27-,28-,29-,38?,39+,40-/m0/s1

InChI Key

RFRIIINGCQOYCL-QCPFSNFXSA-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

Anthracyclinone-skeleton
Anthracycline
Tetracenequinone
Aminoglycoside core
1,4-anthraquinone
9,10-anthraquinone
Anthracene
O-glycosyl compound
Glycosyl compound
Disaccharide
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
Benzenoid
Oxane
Vinylogous acid
Tertiary alcohol
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
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	3.87	ChemAxon
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	10.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	231.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	196.43 m³·mol⁻¹	ChemAxon
Polarizability	81.45 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

C00018384

Chemspider ID

138547

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoshimoto A, Matsuzawa Y, Matsushita Y, Oki T, Takeuchi T, Umezawa H: Trisarubicinol, new antitumor anthracycline antibiotic. J Antibiot (Tokyo). 1981 Nov;34(11):1492-4. doi: 10.7164/antibiotics.34.1492. [PubMed:7319909 ]
LOTUS database [Link]

Showing NP-Card for (8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione (NP0259986)

MOL for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0259986 ((8s)-10-{[(2r,4s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-9,10-dihydro-7h-tetracene-5,12-dione)