NP-MRD: Showing NP-Card for (2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid (NP0143504)

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Record Information

Version

2.0

Created at

2022-09-01 22:16:25 UTC

Updated at

2022-09-01 22:16:25 UTC

NP-MRD ID

NP0143504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid

Description

Benanomicin A belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. (2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid was first documented in 2007 (PMID: 17907132). Based on a literature review a small amount of articles have been published on Benanomicin A (PMID: 30652080) (PMID: 18667788).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200162D          

 59 65  0  0  1  0            999 V2000
    7.8482    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0555    1.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4611    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6592    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2629   -1.1892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6684    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2813    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832    1.6710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6868    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850   -0.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2905   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961    1.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0782    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    2.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    2.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    2.2430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726    3.0439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0782    3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653    3.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    2.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    4.0735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3089    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    1.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -1.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5163   -1.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.5621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5071   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -3.5917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4979   -3.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -4.1638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3089   -4.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -3.9350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2763   -4.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690   -4.2782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2671   -3.4773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597   -3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542   -3.8206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4469   -3.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561   -4.6214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0505   -5.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -4.8502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4653   -5.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -3.1341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6726   -2.9053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034   -1.4180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1016   -2.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758   -1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  4  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 24 33  2  0  0  0  0
 19 33  1  0  0  0  0
 33 34  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 45 44  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 45 52  1  0  0  0  0
 52 53  1  6  0  0  0
 43 54  1  0  0  0  0
 37 54  1  0  0  0  0
 54 55  1  1  0  0  0
 35 56  1  0  0  0  0
 15 56  1  0  0  0  0
 56 57  1  6  0  0  0
 13 58  1  0  0  0  0
  7 58  1  0  0  0  0
 58 59  2  0  0  0  0
M  END

     RDKit          3D

100106  0  0  0  0  0  0  0  0999 V2000
    8.4438   -7.7973   -1.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2139   -6.4307   -1.2267 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9525   -5.9078   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831   -6.7449   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5877   -6.2858   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5984   -7.2143   -0.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4084   -4.9230   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835   -4.0505   -0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7206   -4.5674   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -2.5976   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -1.8962   -0.4540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9911   -2.0260    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -2.9097    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -2.4391    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -1.1154    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580   -0.1949    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -0.6470    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8951    0.1111   -0.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163    1.2184    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    1.6206    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    2.8961    0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271    3.8528    0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225    5.2707    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    3.5268    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891    4.5487    0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2303    4.3084    0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268    5.7619    0.8751 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652    6.9530    0.9736 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5408    7.0179    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595    7.2497    2.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231    8.2838    2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067    6.3972    3.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    2.1799    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153    1.8686    0.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1438    0.5171    0.1683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3162    0.9029   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    1.2468   -0.5122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9864    2.4544   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1395    2.7569   -0.7451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2211    3.2356    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7820    1.6854   -1.5590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1050    2.0571   -1.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7566    0.3462   -0.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9081    0.1018   -0.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6706   -0.9456   -0.6506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9275   -0.5832   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6788   -1.6710   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9836   -2.5959   -0.3842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8627   -3.9305   -0.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5446   -1.1977    1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6932   -2.0938    0.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.8651   -1.0481   -0.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7218   -1.4937    1.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007   -4.3517    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -5.1237    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9310   -8.3804   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5192   -8.0394   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0534   -8.1796   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9932   -7.8120   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630   -7.1336   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5676   -3.9057   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627   -3.1238    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350   -0.0072   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5042    3.2218    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081    5.3182    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729    5.8688   -0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    5.6575    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    4.4388   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204    7.8153    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891    6.6324   -0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0512    2.9983   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1382   -1.3547   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2065   -2.1739   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6328   -1.2606   -1.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0570   -2.4666   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5788   -4.1877   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 65  1  0
M  END


  Mrv1652309022200162D          

 59 65  0  0  1  0            999 V2000
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   -3.0505   -5.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4653   -5.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
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 24 33  2  0  0  0  0
 19 33  1  0  0  0  0
 33 34  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 45 44  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 45 52  1  0  0  0  0
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 37 54  1  0  0  0  0
 54 55  1  1  0  0  0
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 15 56  1  0  0  0  0
 56 57  1  6  0  0  0
 13 58  1  0  0  0  0
  7 58  1  0  0  0  0
 58 59  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0143504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C(O)=C4C(=C3)[C@H](O)[C@@H](O[C@@H]3O[C@H](C)[C@H](O)[C@H](O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@H]3O)C3=C4C(O)=C(C(O)=N[C@H](C)C(O)=O)C(C)=C3)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H41NO19/c1-10-5-17-23(30(48)20(10)36(52)40-11(2)37(53)54)22-15(8-16-24(31(22)49)27(45)14-6-13(55-4)7-18(41)21(14)26(16)44)28(46)34(17)58-39-33(51)35(25(43)12(3)57-39)59-38-32(50)29(47)19(42)9-56-38/h5-8,11-12,19,25,28-29,32-35,38-39,41-43,46-51H,9H2,1-4H3,(H,40,52)(H,53,54)/t11-,12-,19-,25+,28+,29+,32-,33-,34+,35+,38+,39+/m1/s1

> <INCHI_KEY>
GOYUMGXIFMGKFN-NUVDETJMSA-N

> <FORMULA>
C39H41NO19

> <MOLECULAR_WEIGHT>
827.745

> <EXACT_MASS>
827.227278104

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
82.70707442141428

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-({[(10S,11S)-10-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{16,21}]docosa-1(14),2,4(9),5,7,12,16,18,20-nonaen-6-yl](hydroxy)methylidene}amino)propanoic acid

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
2.4505369123333347

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.853173765794322

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1246932271156953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.67268677105731

> <JCHEM_POLAR_SURFACE_AREA>
332.24999999999994

> <JCHEM_REFRACTIVITY>
197.13320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-({[(10S,11S)-10-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{16,21}]docosa-1(14),2,4(9),5,7,12,16,18,20-nonaen-6-yl](hydroxy)methylidene}amino)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      14.650   2.478   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.170   2.906   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.061   1.838   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.431   0.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.321  -0.725   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.691  -2.220   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.841  -0.298   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.471   1.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.581   2.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.992   1.624   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.622   3.119   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.882   0.556   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.252  -0.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.142  -2.006   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.663  -1.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.293  -0.084   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.403   0.984   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.033   2.478   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.813   0.343   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.704  -0.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.224  -0.298   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.146   1.197   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.625   1.624   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.964   2.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.594   3.760   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.704   4.828   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      -0.886   4.187   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -1.256   5.682   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.146   6.750   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.735   6.109   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.845   5.041   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.105   7.604   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.443   1.838   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.553   2.906   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.073  -2.220   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.964  -3.288   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334  -4.783   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.813  -5.210   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.183  -6.705   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.663  -7.132   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.073  -7.772   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.443  -9.267   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.594  -7.345   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.516  -8.413   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -1.995  -7.986   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.365  -6.491   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -3.845  -6.064   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.955  -7.132   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -6.434  -6.705   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.585  -8.627   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -5.694  -9.694   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -3.105  -9.054   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -2.735 -10.549   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.224  -5.850   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -1.256  -5.423   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       3.553  -2.647   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       3.923  -4.142   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       8.732  -1.366   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       9.101  -2.861   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   58                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14   58                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   56                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   33                                                  
CONECT   20   19   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   24   19   34                                                  
CONECT   34   33                                                            
CONECT   35   20   36   56                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   54                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   54                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   52                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   45   53                                                  
CONECT   53   52                                                            
CONECT   54   43   37   55                                                  
CONECT   55   54                                                            
CONECT   56   35   15   57                                                  
CONECT   57   56                                                            
CONECT   58   13    7   59                                                  
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  130    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₄₁NO₁₉

Average Mass

827.7450 Da

Monoisotopic Mass

827.22728 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(C(O)=C4C(=C3)[C@H](O)[C@@H](O[C@@H]3O[C@H](C)[C@H](O)[C@H](O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@H]3O)C3=C4C(O)=C(C(O)=N[C@H](C)C(O)=O)C(C)=C3)C(=O)C2=C1

InChI Identifier

InChI=1S/C39H41NO19/c1-10-5-17-23(30(48)20(10)36(52)40-11(2)37(53)54)22-15(8-16-24(31(22)49)27(45)14-6-13(55-4)7-18(41)21(14)26(16)44)28(46)34(17)58-39-33(51)35(25(43)12(3)57-39)59-38-32(50)29(47)19(42)9-56-38/h5-8,11-12,19,25,28-29,32-35,38-39,41-43,46-51H,9H2,1-4H3,(H,40,52)(H,53,54)/t11-,12-,19-,25+,28+,29+,32-,33-,34+,35+,38+,39+/m1/s1

InChI Key

GOYUMGXIFMGKFN-NUVDETJMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Phenanthrene
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
2-naphthalenecarboxamide
2-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
Alanine or derivatives
1-naphthol
O-glycosyl compound
Alpha-amino acid or derivatives
Salicylic acid or derivatives
Anisole
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Vinylogous acid
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	1.08	ALOGPS
logS	-3	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017923

Chemspider ID

4576633

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5464367

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tamiya M, Ohmori K, Kitamura M, Kato H, Arai T, Oorui M, Suzuki K: General synthesis route to benanomicin-pradimicin antibiotics. Chemistry. 2007;13(35):9791-823. doi: 10.1002/chem.200700863. [PubMed:17907132 ]
Kuraoka T, Ishiyama A, Oyamada H, Ogawa Y, Kobayashi H: Presence of O-glycosidically linked oligosaccharides in the cell wall mannan of Candida krusei purified with Benanomicin A. FEBS Open Bio. 2018 Dec 10;9(1):129-136. doi: 10.1002/2211-5463.12558. eCollection 2019 Jan. [PubMed:30652080 ]
Kumagai H, Umekita M, Sawa R, Takahashi Y, Arisawa A, Isshiki K, Nishimura Y, Akamatsu Y: Generation of new benanomicin analogues by biotransformation using Escherichia coli expressing actinomycete cytochrome P450. J Antibiot (Tokyo). 2008 Jun;61(6):394-9. doi: 10.1038/ja.2008.55. [PubMed:18667788 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid (NP0143504)

MOL for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

3D MOL for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

3D SDF for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

3D-SDF for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

PDB for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

3D PDB for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

SMILES for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

INCHI for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

Structure for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)

3D Structure for NP0143504 ((2r)-2-({[(5s,6s)-5-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)propanoic acid)