NP-MRD: Showing NP-Card for methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0298973)

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Record Information

Version

2.0

Created at

2022-09-10 10:32:55 UTC

Updated at

2022-09-10 10:32:55 UTC

NP-MRD ID

NP0298973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Ciclamycin 0 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 (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces capoamus. Based on a literature review very few articles have been published on Ciclamycin 0.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102212322D          

 57 63  0  0  1  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  1  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  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    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
    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  1  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
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  1  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  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 14 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  8 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 43 50  1  0  0  0  0
 50 51  1  0  0  0  0
 37 51  1  0  0  0  0
 51 52  2  0  0  0  0
 35 53  1  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  1  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

105111  0  0  0  0  0  0  0  0999 V2000
   -6.0540   -2.0895    3.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833   -2.1303    2.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -1.0310    3.1194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4165   -1.0166    4.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -1.4132    2.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352   -0.9440    0.9161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7428    0.2223    0.7786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483   -0.0935   -0.0073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7047    0.7379   -1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816    1.1006   -1.7590 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3599   -0.0281   -2.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168    1.7553   -0.6490 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6201    1.0337   -0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582    1.6015   -0.5922 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7041    1.6560    0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1664    1.7351    0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1634    2.6367   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766    0.3214   -0.3280 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5751    0.2689   -1.1656 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6053   -0.4952   -0.6230 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0807   -1.6082   -1.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7672   -2.6117   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5280   -1.7237    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8952   -2.1472    1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7846   -0.3490   -0.0560 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5911    0.3950    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6658    0.3740   -0.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702   -0.1769   -1.0775 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5942   -1.2209   -2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.8506   -1.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    1.6249    0.6125 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4501    2.0757    1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744    0.2295    0.7644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582   -0.5835    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477    0.0782    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9672    0.4313    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3082    0.1215   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4256   -0.5399   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   -0.8992   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2831   -1.5437   -1.7071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8609   -0.8331   -2.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812   -1.4234   -3.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1701   -0.4645   -3.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5535   -0.7537   -4.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7706   -1.3920   -5.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8281   -0.3832   -5.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6692    0.2658   -4.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2767    0.5464   -2.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1289    1.2025   -2.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0284    0.1901   -2.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6148    0.4880   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4038    1.0931   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2150    0.3134    2.5991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0643    1.1239    3.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5606    2.1941    3.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3620    0.8611    3.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0990    1.7270    4.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3777   -3.1684    3.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9110   -1.6689    3.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9589   -1.6827    4.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0797   -2.1537    1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096   -3.1463    3.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7797   -1.7704    4.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6997   -0.9028    2.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483   -2.5060    2.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866   -1.7807    0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -1.1448   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858    1.6652   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1712    0.1495   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5479    1.7775   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055   -0.2730   -3.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    2.7946   -0.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6731    2.6687   -0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862    2.5678    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230    0.7157    1.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7659    2.0512    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    3.5310   -0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6456   -0.2679    0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3349   -0.9104    0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8741   -1.2017   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3371   -2.0815   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9900   -3.1579    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4427   -3.2592   -1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4518   -0.3878   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9286    0.9303    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3258    1.0518    0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1351   -0.3832    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278   -0.6913   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550   -1.5143   -2.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694   -0.8984   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894   -2.1432   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    2.1608    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313    2.5621    2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.2401    2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    2.8414    1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389    0.9436    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855   -1.8878   -2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102212322D          

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  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  1  0  0  0
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 15 16  1  0  0  0  0
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 28 29  1  6  0  0  0
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 14 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  8 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
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 48 50  2  0  0  0  0
 43 50  1  0  0  0  0
 50 51  1  0  0  0  0
 37 51  1  0  0  0  0
 51 52  2  0  0  0  0
 35 53  1  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  1  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C[C@H](O[C@H]2C[C@H](O)[C@H](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)C2=C(C=C3C(=O)C4=C(O)C=CC(O)=C4C(=O)C3=C2O)[C@H]1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C40H48O17/c1-6-40(50)14-25(29-18(33(40)39(49)51-5)11-19-30(35(29)47)36(48)32-22(43)8-7-21(42)31(32)34(19)46)55-27-12-23(44)38(17(4)53-27)57-28-13-24(45)37(16(3)54-28)56-26-10-9-20(41)15(2)52-26/h7-8,11,15-17,23-28,33,37-38,42-45,47,50H,6,9-10,12-14H2,1-5H3/t15-,16-,17-,23-,24-,25-,26-,27-,28-,33-,37+,38+,40+/m0/s1

> <INCHI_KEY>
IKJUHXISEQVUTJ-NSJQAOPXSA-N

> <FORMULA>
C40H48O17

> <MOLECULAR_WEIGHT>
800.807

> <EXACT_MASS>
800.289150086

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
81.6788920808981

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2R,4S)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2R,4S,5S,6S)-4-hydroxy-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}-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
4.697714213333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.541009972566354

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5665747527620475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.218370473938183

> <JCHEM_POLAR_SURFACE_AREA>
254.26999999999995

> <JCHEM_REFRACTIVITY>
194.11990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,4S)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2R,4S,5S,6S)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-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  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   57  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   53                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28   18   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   14                                                       
CONECT   31   12   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    8                                                       
CONECT   34    6   35   39                                                  
CONECT   35   34   36   53                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   51                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38   34   40                                                  
CONECT   40   39                                                            
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   50                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   43   51                                                  
CONECT   51   50   37   52                                                  
CONECT   52   51                                                            
CONECT   53   35    3   54                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₄₈O₁₇

Average Mass

800.8070 Da

Monoisotopic Mass

800.28915 Da

IUPAC Name

methyl (1R,2R,4S)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2R,4S,5S,6S)-4-hydroxy-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}-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O)C[C@H](O[C@H]2C[C@H](O)[C@H](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)C2=C(C=C3C(=O)C4=C(O)C=CC(O)=C4C(=O)C3=C2O)[C@H]1C(=O)OC

InChI Identifier

InChI=1S/C40H48O17/c1-6-40(50)14-25(29-18(33(40)39(49)51-5)11-19-30(35(29)47)36(48)32-22(43)8-7-21(42)31(32)34(19)46)55-27-12-23(44)38(17(4)53-27)57-28-13-24(45)37(16(3)54-28)56-26-10-9-20(41)15(2)52-26/h7-8,11,15-17,23-28,33,37-38,42-45,47,50H,6,9-10,12-14H2,1-5H3/t15-,16-,17-,23-,24-,25-,26-,27-,28-,33-,37+,38+,40+/m0/s1

InChI Key

IKJUHXISEQVUTJ-NSJQAOPXSA-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 capoamus	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
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
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
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Tertiary alcohol
Vinylogous acid
Methyl ester
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aldehyde
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	4.7	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	254.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	194.12 m³·mol⁻¹	ChemAxon
Polarizability	81.68 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

Not Available

Chemspider ID

9204328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11029152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate (NP0298973)

MOL for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0298973 (methyl (1r,2r,4s)-2-ethyl-2,5,7,10-tetrahydroxy-4-{[(2r,4s,5s,6s)-4-hydroxy-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}-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate)