NP-MRD: Showing NP-Card for (-)-Craigoside C (NP0073999)

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Record Information

Version

2.0

Created at

2022-04-28 19:12:26 UTC

Updated at

2022-04-28 19:12:26 UTC

NP-MRD ID

NP0073999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Craigoside C

Description

Methyl (2S,3E,4S)-3-ethylidene-4-{2-[(2R)-2-[(1R,2R,3S,5S)-2-[({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetyl}oxy)methyl]-5-hydroxy-3-methylcyclopentyl]-3-hydroxypropoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (-)-Craigoside C is found in Jasminum abyssinicum. Based on a literature review very few articles have been published on methyl (2S,3E,4S)-3-ethylidene-4-{2-[(2R)-2-[(1R,2R,3S,5S)-2-[({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetyl}oxy)methyl]-5-hydroxy-3-methylcyclopentyl]-3-hydroxypropoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221122D          

 68 72  0  0  1  0            999 V2000
    1.1270   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -2.4026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470   -2.4026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830   -0.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -2.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -2.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -3.1674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -1.0014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1900   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184    0.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2338    0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    0.0605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7923   -0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436   -2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361    0.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646    1.1224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2777    1.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1061    2.4814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3215    2.7363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    2.1843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1200    1.3773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7331    0.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500    3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477    3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746   -0.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461   -1.5113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5877   -0.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229   -5.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -2.6575    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
  1  5  1  0  0  0  0
  5  6  1  1  0  0  0
  4  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  1  0  0  0
 21 20  1  6  0  0  0
 21 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
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 24 29  1  1  0  0  0
 23 30  1  6  0  0  0
 30 31  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 36  1  1  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 42 41  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 43 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 46 54  1  1  0  0  0
 55 54  1  6  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  1  0  0  0
 59 62  1  6  0  0  0
 58 63  1  1  0  0  0
 57 64  1  6  0  0  0
 64 65  1  0  0  0  0
 36 66  1  0  0  0  0
 66 67  1  0  0  0  0
  2 68  1  6  0  0  0
M  END

     RDKit          3D

132136  0  0  0  0  0  0  0  0999 V2000
    5.1288    1.1319    2.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5302    0.8684    2.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866   -0.2437    2.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5771   -0.2596    1.9707 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7574   -0.4460    0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4923    0.5888    0.1002 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8117    1.1714   -0.9555 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750    2.4138   -1.1959 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6148    3.0335   -2.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1982    4.2909   -2.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8311    2.3738   -1.5352 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3534    3.6553   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6258    1.3763   -0.7364 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7488    1.0134   -1.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8283    0.1198   -0.4514 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5094   -0.6279    0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0702   -1.3690    2.7417 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2364   -2.1970    3.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -2.3402    3.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1362   -3.1926    4.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6966   -3.8259    5.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933   -3.4299    3.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -4.3021    4.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4370   -1.5333    2.1073 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0193   -1.6564    1.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.8057    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -0.1991   -0.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385   -0.7121    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057    0.0431   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975   -0.0488   -1.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9691    0.7589   -2.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5374    0.3155   -3.3864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829   -1.4306   -0.9205 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4076   -2.3566   -1.9788 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6948   -2.8030   -1.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848   -3.5354   -1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622   -2.9497   -1.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8515   -3.1980   -2.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354   -1.5095   -1.1498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3694   -0.7989   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7209   -0.7813   -0.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7764   -1.5887   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -2.8175    0.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2092   -1.3232   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5368   -0.0116   -0.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0724    1.1779   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    2.0341   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763    1.8395   -1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6089    3.1306    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    3.9495   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8236    1.4146    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8951    0.5630    1.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7905    0.3103    0.2532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7065    1.3459    0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9660    0.8340    0.4638 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.7712    1.1141   -0.6346 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9786    0.4417   -0.6076 C   0  0  2  0  0  0  0  0  0  0  0  0
  -12.6883    0.8013   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8998    0.3897   -3.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8002    1.0426    0.5148 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.9391    0.2621    0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0514    1.1283    1.8032 C   0  0  2  0  0  0  0  0  0  0  0  0
  -12.6908    2.1298    2.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6006    1.4515    1.6740 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9656    1.0570    2.8568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9903    0.2624   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4901    0.4414   -2.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311    0.3749   -3.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365    1.6034    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    2.0134    3.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5876    0.3867    3.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2273    1.7441    2.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0573    0.6694    2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7497    1.3207    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2265    3.0159   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5672    3.2270   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6537    2.4123   -3.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3062    4.7025   -1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9532    2.1962   -2.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1599    3.5928   -0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221122D          

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M  END
> <DATABASE_ID>
NP0073999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OC[C@@H](CO)[C@@H]1[C@@H](O)C[C@H](C)[C@H]1COC(=O)C[C@H]1\C(=C/C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C44H64O24/c1-6-20-22(25(39(57)59-4)16-63-41(20)67-43-37(55)35(53)33(51)28(12-46)65-43)9-30(49)61-14-19(11-45)32-24(18(3)8-27(32)48)15-62-31(50)10-23-21(7-2)42(64-17-26(23)40(58)60-5)68-44-38(56)36(54)34(52)29(13-47)66-44/h6-7,16-19,22-24,27-29,32-38,41-48,51-56H,8-15H2,1-5H3/b20-6+,21-7+/t18-,19+,22-,23-,24+,27-,28+,29+,32-,33+,34+,35-,36-,37+,38+,41-,42-,43-,44-/m0/s1

> <INCHI_KEY>
YOJIRWNGIVNEKQ-NXHXVPNMSA-N

> <FORMULA>
C44H64O24

> <MOLECULAR_WEIGHT>
976.972

> <EXACT_MASS>
976.378752941

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
97.81649552193319

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3E,4S)-3-ethylidene-4-(2-{[(1R,2R,3S,5S)-2-[(2R)-1-({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetyl}oxy)-3-hydroxypropan-2-yl]-3-hydroxy-5-methylcyclopentyl]methoxy}-2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-3.158149794

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.427085731199067

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.9055560407394

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288235

> <JCHEM_POLAR_SURFACE_AREA>
362.88000000000005

> <JCHEM_REFRACTIVITY>
226.18120000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5E,6S)-5-ethylidene-4-(2-{[(1R,2R,3S,5S)-2-[(2R)-1-({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydropyran-4-yl]acetyl}oxy)-3-hydroxypropan-2-yl]-3-hydroxy-5-methylcyclopentyl]methoxy}-2-oxoethyl)-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

> <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       2.104  -3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.580  -4.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.088  -4.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.342  -1.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.377  -4.961   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.521  -3.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.986  -4.406   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.306  -5.912   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.130  -3.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.810  -1.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.955  -0.839   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.634   0.667   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.170   1.143   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.025   0.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.346  -1.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.201  -2.424   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.575  -3.831   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.561   0.589   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.241   2.095   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.385   3.126   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.065   4.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.600   5.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.544   4.077   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.224   2.571   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.369   1.541   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.009   4.553   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.280   6.614   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.209   5.662   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.889   7.169   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -7.419  -1.315   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -7.739  -2.821   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -8.564  -0.284   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.243   1.222   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -2.469 -10.171   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0     -14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       4.044  -4.961   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   68                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23   31                                                       
CONECT   31   30                                                            
CONECT   32   13   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36    3   37   66                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   49                                                  
CONECT   43   42   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   43   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   42   50                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52                                                            
CONECT   54   46   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   64                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60   62                                                  
CONECT   60   59   55   61                                                  
CONECT   61   60                                                            
CONECT   62   59                                                            
CONECT   63   58                                                            
CONECT   64   57   65                                                       
CONECT   65   64                                                            
CONECT   66   36   67                                                       
CONECT   67   66                                                            
CONECT   68    2                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3E,4S)-3-ethylidene-4-{2-[(2R)-2-[(1R,2R,3S,5S)-2-[({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetyl}oxy)methyl]-5-hydroxy-3-methylcyclopentyl]-3-hydroxypropoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₄₄H₆₄O₂₄

Average Mass

976.9720 Da

Monoisotopic Mass

976.37875 Da

IUPAC Name

methyl (2S,3E,4S)-3-ethylidene-4-(2-{[(1R,2R,3S,5S)-2-[(2R)-1-({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetyl}oxy)-3-hydroxypropan-2-yl]-3-hydroxy-5-methylcyclopentyl]methoxy}-2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5E,6S)-5-ethylidene-4-(2-{[(1R,2R,3S,5S)-2-[(2R)-1-({2-[(2S,3E,4S)-3-ethylidene-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydropyran-4-yl]acetyl}oxy)-3-hydroxypropan-2-yl]-3-hydroxy-5-methylcyclopentyl]methoxy}-2-oxoethyl)-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OC[C@@H](CO)[C@@H]1[C@@H](O)C[C@H](C)[C@H]1COC(=O)C[C@H]1\C(=C/C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

InChI=1S/C44H64O24/c1-6-20-22(25(39(57)59-4)16-63-41(20)67-43-37(55)35(53)33(51)28(12-46)65-43)9-30(49)61-14-19(11-45)32-24(18(3)8-27(32)48)15-62-31(50)10-23-21(7-2)42(64-17-26(23)40(58)60-5)68-44-38(56)36(54)34(52)29(13-47)66-44/h6-7,16-19,22-24,27-29,32-38,41-48,51-56H,8-15H2,1-5H3/b20-6+,21-7+/t18-,19+,22-,23-,24+,27-,28+,29+,32-,33+,34+,35-,36-,37+,38+,41-,42-,43-,44-/m0/s1

InChI Key

YOJIRWNGIVNEKQ-NXHXVPNMSA-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
Jasminum abyssinicum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Tetracarboxylic acid or derivatives
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Sugar acid
Cyclopentanol
Monosaccharide
Oxane
Vinylogous ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-3.2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	362.88 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	226.18 m³·mol⁻¹	ChemAxon
Polarizability	97.82 Å³	ChemAxon
Number of Rings	5	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

162987161

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Craigoside C (NP0073999)

MOL for NP0073999 ((-)-Craigoside C)

3D MOL for NP0073999 ((-)-Craigoside C)

3D SDF for NP0073999 ((-)-Craigoside C)

3D-SDF for NP0073999 ((-)-Craigoside C)

PDB for NP0073999 ((-)-Craigoside C)

3D PDB for NP0073999 ((-)-Craigoside C)

SMILES for NP0073999 ((-)-Craigoside C)

INCHI for NP0073999 ((-)-Craigoside C)

Structure for NP0073999 ((-)-Craigoside C)

3D Structure for NP0073999 ((-)-Craigoside C)