NP-MRD: Showing NP-Card for (2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid (NP0298653)

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Record Information

Version

2.0

Created at

2022-09-10 10:03:16 UTC

Updated at

2022-09-10 10:03:16 UTC

NP-MRD ID

NP0298653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

Description

(2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methyl-1H-imidazol-4-yl)propanoic acid belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid is found in Duttaphrynus melanostictus. Based on a literature review very few articles have been published on (2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methyl-1H-imidazol-4-yl)propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102212032D          

 51 56  0  0  1  0            999 V2000
   -2.1262   -4.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -4.6725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -3.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -4.1295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1852   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0446  -10.4520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8516  -10.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1065   -9.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9135   -9.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4655   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2725   -9.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2106  -10.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4036  -10.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091  -11.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8886  -11.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0496  -10.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -5.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  4  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  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  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 46 45  1  6  0  0  0
 23 46  1  0  0  0  0
 46 47  1  0  0  0  0
 20 47  1  0  0  0  0
  7 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
  5 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END

     RDKit          3D

106111  0  0  0  0  0  0  0  0999 V2000
   12.5602    1.2585   -2.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3412    0.6619   -1.6244 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1353    0.5062   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9302   -0.0667   -0.1550 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3780   -0.2720   -1.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0703   -0.8707   -1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -1.2446   -0.3369 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2328   -0.1342    0.4108 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0325    0.5992    1.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1119    2.0211    1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    0.2981    2.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762   -0.3796    3.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2366    0.3432    2.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157    0.4620    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791   -0.9369    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396   -0.7570   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    0.0512   -0.9343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101    1.2589   -1.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.4790   -0.6180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564    0.2853   -0.7214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0500   -0.3188   -1.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.9853   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -0.4613    0.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3349   -1.5578    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -1.2703    2.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893   -0.2596    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9225   -0.4974    1.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3315    0.0008    1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8977    0.4430    0.2291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9440    1.5258    0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5923   -0.7260   -0.4501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0688   -0.5133   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8775   -1.2369    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2350   -1.0282    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7780   -0.1128   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.9758    0.5536   -1.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0821    0.2816   -2.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9766    1.0676   -0.7612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3161    2.4143   -1.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6032    1.1341   -0.1745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5738    1.8417   -0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    1.9899   -0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090    0.7822    0.7194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5331    0.5923    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2438   -2.2974    0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7435   -2.0652    1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4483   -3.4938   -0.3427 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2813    0.1932   -2.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3441    0.4914   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3242   -0.1079    3.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4553   -1.7114   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4784   -1.1085   -2.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2066    0.2065   -3.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
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 46102  1  1
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 31 88  1  1
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 38 91  1  0
 34 90  1  0
 33 89  1  0
 47103  1  0
 47104  1  0
 50105  1  0
 51106  1  0
M  END


  Mrv1652309102212032D          

 51 56  0  0  1  0            999 V2000
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    9.2881   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1852   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0446  -10.4520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8516  -10.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1065   -9.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9135   -9.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4655   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2725   -9.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2106  -10.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4036  -10.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091  -11.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8886  -11.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0496  -10.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -5.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  4  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  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  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 46 45  1  6  0  0  0
 23 46  1  0  0  0  0
 46 47  1  0  0  0  0
 20 47  1  0  0  0  0
  7 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
  5 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC(C[C@H](N=C(O)CCCCCCC(=O)O[C@H]2CC[C@@]3(CO)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=COC(=O)C=C3)C2)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H55N3O9/c1-37-16-14-30-31(39(37,49)18-15-29(37)25-9-12-34(45)50-22-25)11-10-26-19-28(13-17-38(26,30)23-43)51-35(46)8-6-4-3-5-7-33(44)41-32(36(47)48)20-27-21-42(2)24-40-27/h9,12,21-22,24,26,28-32,43,49H,3-8,10-11,13-20,23H2,1-2H3,(H,41,44)(H,47,48)/t26-,28+,29-,30+,31-,32+,37-,38-,39+/m1/s1

> <INCHI_KEY>
DRFIGWOPALMIBP-PEHYSWGKSA-N

> <FORMULA>
C39H55N3O9

> <MOLECULAR_WEIGHT>
709.881

> <EXACT_MASS>
709.393830363

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
77.92503232030602

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

> <JCHEM_LOGP>
2.7682400559551845

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.569482686266475

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.862962487308291

> <JCHEM_PKA_STRONGEST_BASIC>
6.487923171672059

> <JCHEM_POLAR_SURFACE_AREA>
180.76999999999998

> <JCHEM_REFRACTIVITY>
188.42400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

> <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      -3.969  -8.883   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.437  -8.722   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.667  -7.388   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.161  -7.708   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667 -12.320   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -15.400   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.672 -13.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.746 -17.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.483 -19.510   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      23.990 -19.190   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.466 -17.726   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.972 -17.405   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.002 -18.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      28.509 -18.230   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      26.526 -20.015   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      25.020 -20.335   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.857 -20.917   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.325 -20.756   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      18.759 -20.155   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -1.407  -9.866   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   48                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   47                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26   46                                             
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   43                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   41                                             
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   31   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   29   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   26   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   23   47                                                  
CONECT   47   46   20                                                       
CONECT   48    7   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-[(1-Hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0,.0,]heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methyl-1H-imidazol-4-yl)propanoate	Generator

Chemical Formula

C₃₉H₅₅N₃O₉

Average Mass

709.8810 Da

Monoisotopic Mass

709.39383 Da

IUPAC Name

(2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

Traditional Name

(2S)-2-[(1-hydroxy-8-{[(1S,2R,5S,7R,10R,11S,14S,15R)-11-hydroxy-2-(hydroxymethyl)-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CN1C=NC(C[C@H](N=C(O)CCCCCCC(=O)O[C@H]2CC[C@@]3(CO)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=COC(=O)C=C3)C2)C(O)=O)=C1

InChI Identifier

InChI=1S/C39H55N3O9/c1-37-16-14-30-31(39(37,49)18-15-29(37)25-9-12-34(45)50-22-25)11-10-26-19-28(13-17-38(26,30)23-43)51-35(46)8-6-4-3-5-7-33(44)41-32(36(47)48)20-27-21-42(2)24-40-27/h9,12,21-22,24,26,28-32,43,49H,3-8,10-11,13-20,23H2,1-2H3,(H,41,44)(H,47,48)/t26-,28+,29-,30+,31-,32+,37-,38-,39+/m1/s1

InChI Key

DRFIGWOPALMIBP-PEHYSWGKSA-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
Duttaphrynus melanostictus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroid ester
19-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Pyranone
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
N-substituted imidazole
Pyran
Azole
Cyclic alcohol
Heteroaromatic compound
Imidazole
Tertiary alcohol
Lactone
Carboxylic acid ester
Organic 1,3-dipolar compound
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Oxacycle
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.77	ChemAxon
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	6.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	180.77 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	188.42 m³·mol⁻¹	ChemAxon
Polarizability	77.93 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162954641

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid (NP0298653)

MOL for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

3D MOL for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

3D SDF for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

3D-SDF for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

PDB for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

3D PDB for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

SMILES for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

INCHI for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

Structure for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)

3D Structure for NP0298653 ((2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid)