NP-MRD: Showing NP-Card for (-)-Gordonoside I (NP0074432)

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Record Information

Version

2.0

Created at

2022-04-28 19:40:50 UTC

Updated at

2022-04-28 19:40:50 UTC

NP-MRD ID

NP0074432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Gordonoside I

Description

(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate 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. (-)-Gordonoside I is found in Hoodia gordonii . Based on a literature review very few articles have been published on (1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221402D          

 80 88  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   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
    5.9193    1.1884    0.0000 C   0  0  0  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  1  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
    5.3587   -0.3634    0.0000 C   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
    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  2  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  2  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  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
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    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    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
    2.6421   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739   -2.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0117    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0405    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1966    3.9518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4769    4.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2890    4.8730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.7284    3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6329    4.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9769    3.9020    0.0000 O   0  0  0  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  2  0  0  0  0  0  0  0  0  0
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   12.6678    0.9435    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
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708   -1.8697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8905   -2.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4223   -3.2764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2345   -3.1312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5148   -2.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9829   -1.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3269   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663   -3.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1420   -4.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2632   -0.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3208    3.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3814    5.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  2 31  1  1  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 35 40  1  6  0  0  0
 41 40  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  1  0  0  0
 44 48  1  6  0  0  0
 49 48  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 49 54  1  0  0  0  0
 53 55  1  6  0  0  0
 55 56  1  0  0  0  0
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 58 57  1  1  0  0  0
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 59 60  1  0  0  0  0
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 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
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 66 67  1  0  0  0  0
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 78 79  1  0  0  0  0
 34 80  1  1  0  0  0
M  END

     RDKit          3D

176184  0  0  0  0  0  0  0  0999 V2000
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  -12.6029    3.8495    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -14.0353    3.9254    2.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9642    1.7638    1.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4772    1.1160    2.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.8749   -0.2591    0.4933 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.4207   -0.4656    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112   -0.5939   -0.3250 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0791   -0.3699   -1.6712 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.7635   -0.4515   -2.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3591    0.1053   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9330    0.4684   -1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4519   -0.2167    0.1254 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7518   -2.6031   -0.6897 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2829    0.7128   -1.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221402D          

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    9.4769    4.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2890    4.8730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8208    4.2423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5405    3.4663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7284    3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    2.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6329    4.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1647    3.7568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9769    3.9020    0.0000 O   0  0  0  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  2  0  0  0  0  0  0  0  0  0
   12.4163    2.3501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8844    2.9809    0.0000 C   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
   11.3238    1.4290    0.0000 C   0  0  0  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
   13.4799    1.0887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0117    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7314   -0.3179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9193   -0.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6678    0.9435    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
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708   -1.8697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8905   -2.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4223   -3.2764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2345   -3.1312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5148   -2.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9829   -1.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3269   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663   -3.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1420   -4.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2632   -0.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0754   -0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208    3.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5693    5.6489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3814    5.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  2 31  1  1  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 35 40  1  6  0  0  0
 41 40  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  1  0  0  0
 44 48  1  6  0  0  0
 49 48  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 49 54  1  0  0  0  0
 53 55  1  6  0  0  0
 55 56  1  0  0  0  0
 52 57  1  1  0  0  0
 58 57  1  1  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 58 63  1  0  0  0  0
 62 64  1  1  0  0  0
 61 65  1  6  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
 70 72  1  6  0  0  0
 69 73  1  1  0  0  0
 68 74  1  1  0  0  0
 60 75  1  1  0  0  0
 75 76  1  0  0  0  0
 51 77  1  6  0  0  0
 43 78  1  6  0  0  0
 78 79  1  0  0  0  0
 34 80  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@@H](OC)[C@H](O[C@H]3C[C@@H](OC)[C@H](O[C@H]4C[C@H](O)[C@H](O)[C@@H](C)O4)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C60H96O20/c1-15-29(2)57(64)76-46-23-40-39(60(65)21-19-38(30(3)61)59(46,60)10)17-16-36-22-37(18-20-58(36,40)9)75-48-25-42(66-11)54(32(5)71-48)78-50-27-44(68-13)56(34(7)73-50)80-51-28-45(69-14)55(35(8)74-51)79-49-26-43(67-12)53(33(6)72-49)77-47-24-41(62)52(63)31(4)70-47/h15-16,31-35,37-56,62-63,65H,17-28H2,1-14H3/b29-15+/t31-,32-,33-,34-,35-,37+,38-,39-,40+,41+,42+,43-,44+,45-,46-,47+,48+,49+,50+,51+,52-,53-,54-,55-,56-,58+,59+,60+/m1/s1

> <INCHI_KEY>
UOCWRQGDLHMXII-PGAUVFAXSA-N

> <FORMULA>
C60H96O20

> <MOLECULAR_WEIGHT>
1137.408

> <EXACT_MASS>
1136.649495491

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
176

> <JCHEM_AVERAGE_POLARIZABILITY>
126.75570465698405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
6.938206520000001

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.053854834496146

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.101481901825785

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2067140449656506

> <JCHEM_POLAR_SURFACE_AREA>
233.27999999999992

> <JCHEM_REFRACTIVITY>
286.3523999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,14S,15S,16R)-14-acetyl-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.558  -2.907   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.925  -4.117   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.441  -3.846   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.401  -5.566   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.394  -6.743   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.871  -8.191   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.885  -5.837   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.619   6.564   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.142   8.012   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      17.167   7.377   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.690   8.825   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      19.206   9.096   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.199   7.919   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      19.676   6.471   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      18.160   6.199   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      20.668   5.293   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      21.715   8.190   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      22.708   7.013   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      24.223   7.284   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      25.216   6.106   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.693   4.658   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.177   4.387   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.184   5.564   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      21.138   2.667   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      25.686   3.481   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      25.162   2.032   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.155   0.855   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      25.632  -0.593   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      24.116  -0.864   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      23.123   0.313   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      23.647   1.761   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      24.586  -3.490   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      24.062  -4.939   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      25.055  -6.116   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      26.571  -5.845   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      27.094  -4.396   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      26.101  -3.219   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      28.610  -4.125   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      27.564  -7.022   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      24.532  -7.564   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      26.625  -1.771   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      28.141  -1.500   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      26.732   6.377   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0      19.729  10.545   0.000  0.00  0.00           O+0
HETATM   79  C   UNK     0      21.245  10.816   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      17.636   4.751   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   18   23                                             
CONECT   15   14    7   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   80                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36   32                                                       
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   78                                                  
CONECT   44   43   45   48                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45   41                                                       
CONECT   47   45                                                            
CONECT   48   44   49                                                       
CONECT   49   48   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   77                                                  
CONECT   52   51   53   57                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53   49                                                       
CONECT   55   53   56                                                       
CONECT   56   55                                                            
CONECT   57   52   58                                                       
CONECT   58   57   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   75                                                  
CONECT   61   60   62   65                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62   58                                                       
CONECT   64   62                                                            
CONECT   65   61   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66   68                                                       
CONECT   68   67   69   74                                                  
CONECT   69   68   70   73                                                  
CONECT   70   69   71   72                                                  
CONECT   71   70   66                                                       
CONECT   72   70                                                            
CONECT   73   69                                                            
CONECT   74   68                                                            
CONECT   75   60   76                                                       
CONECT   76   75                                                            
CONECT   77   51                                                            
CONECT   78   43   79                                                       
CONECT   79   78                                                            
CONECT   80   34                                                            
MASTER        0    0    0    0    0    0    0    0   80    0  176    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,10R,11S,14S,15S,16R)-14-Acetyl-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4R,5R,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₆₀H₉₆O₂₀

Average Mass

1137.4080 Da

Monoisotopic Mass

1136.64950 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@H]2C[C@@H](OC)[C@H](O[C@H]3C[C@@H](OC)[C@H](O[C@H]4C[C@H](O)[C@H](O)[C@@H](C)O4)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1

InChI Identifier

InChI=1S/C60H96O20/c1-15-29(2)57(64)76-46-23-40-39(60(65)21-19-38(30(3)61)59(46,60)10)17-16-36-22-37(18-20-58(36,40)9)75-48-25-42(66-11)54(32(5)71-48)78-50-27-44(68-13)56(34(7)73-50)80-51-28-45(69-14)55(35(8)74-51)79-49-26-43(67-12)53(33(6)72-49)77-47-24-41(62)52(63)31(4)70-47/h15-16,31-35,37-56,62-63,65H,17-28H2,1-14H3/b29-15+/t31-,32-,33-,34-,35-,37+,38-,39-,40+,41+,42+,43-,44+,45-,46-,47+,48+,49+,50+,51+,52-,53-,54-,55-,56-,58+,59+,60+/m1/s1

InChI Key

UOCWRQGDLHMXII-PGAUVFAXSA-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
Hoodia gordonii	Plant	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

Steroidal glycoside
Oligosaccharide
Pregnane-skeleton
20-oxosteroid
Steroid ester
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.71	ALOGPS
logP	6.94	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	233.28 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	286.35 m³·mol⁻¹	ChemAxon
Polarizability	126.76 Å³	ChemAxon
Number of Rings	9	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

163072591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Gordonoside I (NP0074432)

MOL for NP0074432 ((-)-Gordonoside I)

3D MOL for NP0074432 ((-)-Gordonoside I)

3D SDF for NP0074432 ((-)-Gordonoside I)

3D-SDF for NP0074432 ((-)-Gordonoside I)

PDB for NP0074432 ((-)-Gordonoside I)

3D PDB for NP0074432 ((-)-Gordonoside I)

SMILES for NP0074432 ((-)-Gordonoside I)

INCHI for NP0074432 ((-)-Gordonoside I)

Structure for NP0074432 ((-)-Gordonoside I)

3D Structure for NP0074432 ((-)-Gordonoside I)