NP-MRD: Showing NP-Card for (-)-Mycaloside D (NP0080020)

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Record Information

Version

2.0

Created at

2022-04-29 01:04:16 UTC

Updated at

2022-04-29 01:04:16 UTC

NP-MRD ID

NP0080020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Mycaloside D

Description

[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5S)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-3,5-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (-)-Mycaloside D is found in Mycale laxissima. Based on a literature review very few articles have been published on [(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5S)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-3,5-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203042D          

 77 84  0  0  1  0            999 V2000
    9.6996    1.1386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9799    1.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7920    2.0597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3238    1.4290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0435    0.6531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2314    0.5079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5466   -2.1602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7345   -2.3054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4542   -3.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981   -2.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0178   -3.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2057   -3.6622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5496   -4.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8445    0.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4163    2.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8844    2.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1647    3.7568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9769    3.9020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5087    3.2713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2284    2.4954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7602    1.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208    3.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2572    4.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6329    4.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9132    5.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    2.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  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  6  0  0  0
 11 10  1  6  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
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 15 18  1  6  0  0  0
 14 19  1  6  0  0  0
 13 20  1  6  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  1  1  0  0  0
 45 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 41 54  1  6  0  0  0
 39 55  1  1  0  0  0
 32 56  1  0  0  0  0
 28 56  1  0  0  0  0
 56 57  1  1  0  0  0
 31 58  1  1  0  0  0
 22 59  1  1  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 61 63  1  0  0  0  0
  5 64  1  6  0  0  0
  4 65  1  1  0  0  0
 66 65  1  6  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 66 71  1  0  0  0  0
 71 72  1  1  0  0  0
 70 73  1  6  0  0  0
 69 74  1  6  0  0  0
 68 75  1  6  0  0  0
 75 76  1  0  0  0  0
  3 77  1  1  0  0  0
M  END

     RDKit          3D

163170  0  0  0  0  0  0  0  0999 V2000
   -4.1332   -7.5814    2.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0700   -6.3758    1.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1784   -6.1357    1.1771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949   -5.6790    1.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -4.6820    0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8254   -3.2708    0.9289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7221   -2.5408    0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635   -1.2658    0.9488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8299   -0.5354    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3406   -0.3340    0.8271 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4894   -1.1052    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -0.3362   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8062    0.9071   -0.4996 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6092    1.9911   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393    1.2321    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282    1.5824    1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    1.7162    1.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545    1.7838    0.5286 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2483    0.6361   -0.2959 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9738    0.4723   -1.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4566    0.3470   -1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0304    1.4992   -0.7067 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8734    2.7423   -1.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2930    1.4301    0.5911 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6660    1.1306    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.0532   -0.6066    0.9266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0860    0.2048    2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833   -1.3955    0.8003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3198   -0.7401    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5371   -0.6266    0.6838 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5757   -0.8687   -0.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1371   -0.3074   -1.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0465    1.1622   -1.3114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2337    1.7561   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7227    1.7831    0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.0693    4.0765    0.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -8.8058    4.8627    1.5947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.3676    3.8105    2.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7323    3.9812    2.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5847    4.7403    0.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1640    3.4607    0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9156    5.2296   -0.9041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.4971    4.6150   -2.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4568    4.9716   -0.8657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7058    6.1451   -0.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7801    0.8322    1.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9905    1.1588    2.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9851   -2.7447    0.1192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0354   -3.5741   -0.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589   -3.7579   -1.3778 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292203042D          

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    8.5496   -4.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8445    0.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4163    2.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8844    2.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1647    3.7568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9769    3.9020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5087    3.2713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2284    2.4954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7602    1.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208    3.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2572    4.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6329    4.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9132    5.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    2.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  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  6  0  0  0
 11 10  1  6  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
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 15 18  1  6  0  0  0
 14 19  1  6  0  0  0
 13 20  1  6  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  1  1  0  0  0
 45 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 41 54  1  6  0  0  0
 39 55  1  1  0  0  0
 32 56  1  0  0  0  0
 28 56  1  0  0  0  0
 56 57  1  1  0  0  0
 31 58  1  1  0  0  0
 22 59  1  1  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 61 63  1  0  0  0  0
  5 64  1  6  0  0  0
  4 65  1  1  0  0  0
 66 65  1  6  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 66 71  1  0  0  0  0
 71 72  1  1  0  0  0
 70 73  1  6  0  0  0
 69 74  1  6  0  0  0
 68 75  1  6  0  0  0
 75 76  1  0  0  0  0
  3 77  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0080020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](C)\C=C\[C@H](CO)[C@H]1C[C@H](O)[C@H]2[C@@H]3CC=C4[C@@H](O)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H86O24/c1-21(2)22(3)7-8-24(16-54)28-15-29(58)35-25-9-10-27-36(60)31(12-14-52(27,5)26(25)11-13-53(28,35)6)71-51-44(68)47(46(34(74-51)20-69-23(4)57)76-50-42(66)40(64)38(62)33(18-56)73-50)77-48-43(67)45(30(59)19-70-48)75-49-41(65)39(63)37(61)32(17-55)72-49/h7-8,10,21-22,24-26,28-51,54-56,58-68H,9,11-20H2,1-6H3/b8-7+/t22-,24-,25-,26+,28-,29+,30-,31+,32-,33-,34-,35-,36-,37+,38+,39+,40+,41-,42-,43+,44-,45-,46-,47-,48+,49+,50+,51-,52-,53-/m1/s1

> <INCHI_KEY>
JCSQARUNVMBPQH-NWLJNKFFSA-N

> <FORMULA>
C53H86O24

> <MOLECULAR_WEIGHT>
1107.247

> <EXACT_MASS>
1106.550903649

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
163

> <JCHEM_AVERAGE_POLARIZABILITY>
117.41853034510144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5S)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-3,5-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-2.5603815906666636

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.087756101824493

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.676978183312652

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377575208073

> <JCHEM_POLAR_SURFACE_AREA>
383.36000000000007

> <JCHEM_REFRACTIVITY>
263.7756000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5S)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-3,5-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      18.106   2.125   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.629   3.574   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.145   3.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.138   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.615   1.219   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.099   0.948   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      19.045  -3.126   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.568  -1.678   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.077  -2.584   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.554  -4.032   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.038  -4.303   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      19.514  -5.752   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.546  -5.210   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      23.123   0.313   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.613  -4.122   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.599  -0.848   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -4.489  -3.280   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       3.820   3.618   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      11.573   3.667   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      14.497  -3.939   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      15.490  -5.117   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      14.967  -6.565   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      13.451  -6.836   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      15.959  -7.742   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      22.110   0.850   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      23.177   4.387   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      22.184   5.564   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      22.708   7.013   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      24.223   7.284   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      25.216   6.106   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      24.693   4.658   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      25.686   3.481   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      26.732   6.377   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      24.747   8.732   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      21.715   8.190   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      22.238   9.638   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      20.668   5.293   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   77                                                  
CONECT    4    3    5   65                                                  
CONECT    5    4    6   64                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   59                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24    8   26                                                  
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   56                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36   58                                             
CONECT   32   31   33   56                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   31   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   43   55                                             
CONECT   40   39   35   41                                                  
CONECT   41   40   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   39   44                                                  
CONECT   44   43   45   47                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   44   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   41                                                            
CONECT   55   39                                                            
CONECT   56   32   28   57                                                  
CONECT   57   56                                                            
CONECT   58   31                                                            
CONECT   59   22   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61                                                            
CONECT   64    5                                                            
CONECT   65    4   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66   68                                                       
CONECT   68   67   69   75                                                  
CONECT   69   68   70   74                                                  
CONECT   70   69   71   73                                                  
CONECT   71   70   66   72                                                  
CONECT   72   71                                                            
CONECT   73   70                                                            
CONECT   74   69                                                            
CONECT   75   68   76                                                       
CONECT   76   75                                                            
CONECT   77    3                                                            
MASTER        0    0    0    0    0    0    0    0   77    0  168    0
END

View in JSmol

Synonyms

Value

Source

Generator

Chemical Formula

C₅₃H₈₆O₂₄

Average Mass

1107.2470 Da

Monoisotopic Mass

1106.55090 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)\C=C\[C@H](CO)[C@H]1C[C@H](O)[C@H]2[C@@H]3CC=C4[C@@H](O)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C53H86O24/c1-21(2)22(3)7-8-24(16-54)28-15-29(58)35-25-9-10-27-36(60)31(12-14-52(27,5)26(25)11-13-53(28,35)6)71-51-44(68)47(46(34(74-51)20-69-23(4)57)76-50-42(66)40(64)38(62)33(18-56)73-50)77-48-43(67)45(30(59)19-70-48)75-49-41(65)39(63)37(61)32(17-55)72-49/h7-8,10,21-22,24-26,28-51,54-56,58-68H,9,11-20H2,1-6H3/b8-7+/t22-,24-,25-,26+,28-,29+,30-,31+,32-,33-,34-,35-,36-,37+,38+,39+,40+,41-,42-,43+,44-,45-,46-,47-,48+,49+,50+,51-,52-,53-/m1/s1

InChI Key

JCSQARUNVMBPQH-NWLJNKFFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Mycale laxissima	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Ergostane-skeleton
Steroidal glycoside
Trihydroxy bile acid, alcohol, or derivatives
Oligosaccharide
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
21-hydroxysteroid
Diterpenoid
Hydroxysteroid
15-hydroxysteroid
4-hydroxysteroid
Terpene glycoside
Delta-5-steroid
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty alcohol
Fatty acyl
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.75	ALOGPS
logP	-2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	383.36 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	263.78 m³·mol⁻¹	ChemAxon
Polarizability	117.42 Å³	ChemAxon
Number of Rings	8	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

163104531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Mycaloside D (NP0080020)

MOL for NP0080020 ((-)-Mycaloside D)

3D MOL for NP0080020 ((-)-Mycaloside D)

3D SDF for NP0080020 ((-)-Mycaloside D)

3D-SDF for NP0080020 ((-)-Mycaloside D)

PDB for NP0080020 ((-)-Mycaloside D)

3D PDB for NP0080020 ((-)-Mycaloside D)

SMILES for NP0080020 ((-)-Mycaloside D)

INCHI for NP0080020 ((-)-Mycaloside D)

Structure for NP0080020 ((-)-Mycaloside D)

3D Structure for NP0080020 ((-)-Mycaloside D)