NP-MRD: Showing NP-Card for Dulcoside A (NP0074709)

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Record Information

Version

2.0

Created at

2022-04-28 20:01:09 UTC

Updated at

2022-04-28 20:01:09 UTC

NP-MRD ID

NP0074709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dulcoside A

Description

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4R,5R,9S,10S,13S)-13-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety. Dulcoside A is found in Stevia rebaudiana . Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4R,5R,9S,10S,13S)-13-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222012D          

 55 61  0  0  1  0            999 V2000
    3.3179    1.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    0.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    0.0351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2043    0.2129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9555    0.9995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5123    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    1.2014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5353    0.5473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8407   -0.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598    1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166    1.5456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0434    2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975    0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105    0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064    1.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593    2.8218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8491    3.2744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8021    4.0980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0653    4.4691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3755    4.0166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4225    3.1929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613    4.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511    3.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    5.2928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4919    4.5506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860    2.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    3.3558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0126    2.9847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7024    3.4372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6554    4.2609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9185    4.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2287    4.1795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    5.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3452    4.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4392    3.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596    2.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5988   -0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4881   -1.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384   -2.1228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9662   -2.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -3.4694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0392   -3.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4114   -3.2102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5610   -2.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9332   -1.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339   -3.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8896   -4.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2948   -4.8159    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 12 18  1  1  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  6  0  0  0
 33 37  1  1  0  0  0
 32 38  1  6  0  0  0
 31 39  1  1  0  0  0
  5 40  1  1  0  0  0
  3 41  1  6  0  0  0
  3 42  1  1  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 45 44  1  6  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 45 50  1  0  0  0  0
 50 51  1  1  0  0  0
 49 52  1  6  0  0  0
 48 53  1  1  0  0  0
 47 54  1  6  0  0  0
 54 55  1  0  0  0  0
M  END

     RDKit          3D

115121  0  0  0  0  0  0  0  0999 V2000
   -3.1608   -2.4201    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.4770    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782   -1.5970    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.2612    0.7347 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3855    0.0511    2.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7050   -0.6122    2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612   -0.2697    1.0268 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0532   -0.3620   -0.3184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7868    0.6957   -1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -1.6359   -1.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -2.7229   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594   -2.2466    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698   -0.9982    1.2115 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1115   -1.3699    2.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1354   -0.0743    1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0628    1.1486    0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4274   -0.6193    0.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5580    0.1758    0.7857 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2836   -0.1892   -0.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9844    0.9144   -0.8203 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0307    0.4885   -1.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6911    1.6565   -2.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5923    1.7281    0.2906 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9334    2.9594    0.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7283    0.9605    1.5721 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9131    0.1903    1.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5356    0.1339    1.9375 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9386    0.5063    3.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492    0.1617   -0.3402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0084    0.1733   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -0.3821   -1.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -0.1898   -0.5443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3959    0.4667   -0.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -0.0197   -1.7634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1537    0.7531   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1944    0.4265   -3.8054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6655    0.5302   -5.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7298    0.1967   -6.0782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7478   -0.9532   -3.6592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8671   -1.9515   -4.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2484   -1.2502   -2.2448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6151   -1.2891   -2.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.1265   -1.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8110   -0.3096   -0.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5515    0.6914    0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6499    0.0648    1.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4128    0.8825    1.9687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4001    0.0043    2.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6153    1.6322    2.9907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6427    3.0207    2.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1731    1.2128    3.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9494   -0.0505    3.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6536    1.3521    1.5878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5211    2.7342    1.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    0.6349    0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1399   -2.3352   -0.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428   -3.3318    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -1.9450    1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -2.3990    0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694    1.1603    2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145   -0.1649    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521   -1.7067    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -0.3743    3.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.7954    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7985    0.3025   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515    1.6359   -0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814    0.7638   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -1.5058   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032   -2.0538   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -3.5155   -0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765   -3.2263    0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5452   -3.0515    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071   -2.0772   -0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -1.8769    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3600   -2.0897    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2026   -0.4597    3.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2038    1.2425    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602    1.5477   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5027    0.0514   -2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7673   -0.2188   -1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0715    2.2615   -2.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6252    2.0062   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5090    3.5779    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8708    1.7092    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6399    0.7808    1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8848   -0.9348    2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6220    0.3482    3.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.2724   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    1.2021   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255   -0.3897   -2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282    0.0857   -2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -1.4670   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -1.0088   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    1.1633   -3.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -0.2483   -5.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    1.5583   -5.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1462    1.0150   -6.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000   -1.0152   -4.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3768   -2.8021   -4.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8630   -2.1995   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2321    1.6221    0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
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 53112  1  1
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 51110  1  1
 52111  1  0
 49108  1  1
 50109  1  0
M  END


  Mrv1652304282222012D          

 55 61  0  0  1  0            999 V2000
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    1.1344    1.2014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.6554    4.2609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9185    4.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.5988   -0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4881   -1.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384   -2.1228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9662   -2.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -3.4694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0392   -3.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4114   -3.2102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5610   -2.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9332   -1.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8896   -4.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2948   -4.8159    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
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  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 12 18  1  1  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  6  0  0  0
 33 37  1  1  0  0  0
 32 38  1  6  0  0  0
 31 39  1  1  0  0  0
  5 40  1  1  0  0  0
  3 41  1  6  0  0  0
  3 42  1  1  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 45 44  1  6  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 45 50  1  0  0  0  0
 50 51  1  1  0  0  0
 49 52  1  6  0  0  0
 48 53  1  1  0  0  0
 47 54  1  6  0  0  0
 54 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](CO)O[C@H]2O[C@@]23C[C@]4(CC2=C)CC[C@@H]2[C@@](C)(CCC[C@@]2(C)C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]4CC3)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H60O17/c1-16-12-37-10-6-20-35(3,8-5-9-36(20,4)34(49)54-32-29(48)26(45)23(42)18(13-39)51-32)21(37)7-11-38(16,15-37)55-33-30(27(46)24(43)19(14-40)52-33)53-31-28(47)25(44)22(41)17(2)50-31/h17-33,39-48H,1,5-15H2,2-4H3/t17-,18+,19-,20+,21+,22-,23+,24+,25+,26-,27-,28-,29+,30+,31+,32-,33-,35+,36+,37+,38-/m0/s1

> <INCHI_KEY>
CANAPGLEBDTCAF-MORBOXIVSA-N

> <FORMULA>
C38H60O17

> <MOLECULAR_WEIGHT>
788.881

> <EXACT_MASS>
788.383050472

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
81.81483613421989

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4R,5R,9S,10S,13S)-13-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
-1.20

> <JCHEM_LOGP>
-1.1142984186666667

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.315096693702387

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.84611836293568

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294395802

> <JCHEM_POLAR_SURFACE_AREA>
274.74999999999994

> <JCHEM_REFRACTIVITY>
184.60580000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4R,5R,9S,10S,13S)-13-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-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       6.193   2.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.658   1.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.618   0.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.115   0.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.650   1.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.690   3.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.118   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.999   1.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.569  -0.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.112   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.964   2.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.081   4.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.659   3.819   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.675   1.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.193   1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.512   0.307   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.252   3.730   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.164   5.267   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.452   6.112   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.364   7.650   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.989   8.342   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.701   7.498   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.789   5.960   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.674   8.190   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.962   7.346   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.901   9.880   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.652   8.494   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.827   5.419   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.115   6.264   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.490   5.571   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.778   6.416   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.690   7.954   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.315   8.646   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.027   7.802   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.227  10.184   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -9.978   8.798   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -10.153   5.723   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -7.578   4.034   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.888  -1.964   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       6.511  -2.448   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       6.232  -3.963   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       7.404  -4.962   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.124  -6.476   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.673  -6.991   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.501  -5.992   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.781  -4.478   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       3.609  -3.479   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       3.050  -6.508   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.394  -8.506   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       8.296  -7.475   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       8.017  -8.990   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   41   42                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   40                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   17                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15   18                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8                                                       
CONECT   18   12   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22                                                            
CONECT   28   21                                                            
CONECT   29   20   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   39                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34                                                            
CONECT   37   33                                                            
CONECT   38   32                                                            
CONECT   39   31                                                            
CONECT   40    5                                                            
CONECT   41    3                                                            
CONECT   42    3   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   54                                                  
CONECT   48   47   49   53                                                  
CONECT   49   48   50   52                                                  
CONECT   50   49   45   51                                                  
CONECT   51   50                                                            
CONECT   52   49                                                            
CONECT   53   48                                                            
CONECT   54   47   55                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  122    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4R,5R,9S,10S,13S)-13-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₃₈H₆₀O₁₇

Average Mass

788.8810 Da

Monoisotopic Mass

788.38305 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](CO)O[C@H]2O[C@@]23C[C@]4(CC2=C)CC[C@@H]2[C@@](C)(CCC[C@@]2(C)C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]4CC3)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C38H60O17/c1-16-12-37-10-6-20-35(3,8-5-9-36(20,4)34(49)54-32-29(48)26(45)23(42)18(13-39)51-32)21(37)7-11-38(16,15-37)55-33-30(27(46)24(43)19(14-40)52-33)53-31-28(47)25(44)22(41)17(2)50-31/h17-33,39-48H,1,5-15H2,2-4H3/t17-,18+,19-,20+,21+,22-,23+,24+,25+,26-,27-,28-,29+,30+,31+,32-,33-,35+,36+,37+,38-/m0/s1

InChI Key

CANAPGLEBDTCAF-MORBOXIVSA-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
Stevia rebaudiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Substituents

Steviol glycoside
Kaurane diterpenoid
Diterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acyl
Oxane
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	-1.2	ALOGPS
logP	-1.1	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	274.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	184.61 m³·mol⁻¹	ChemAxon
Polarizability	81.81 Å³	ChemAxon
Number of Rings	7	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

154496501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dulcoside A (NP0074709)

MOL for NP0074709 (Dulcoside A)

3D MOL for NP0074709 (Dulcoside A)

3D SDF for NP0074709 (Dulcoside A)

3D-SDF for NP0074709 (Dulcoside A)

PDB for NP0074709 (Dulcoside A)

3D PDB for NP0074709 (Dulcoside A)

SMILES for NP0074709 (Dulcoside A)

INCHI for NP0074709 (Dulcoside A)

Structure for NP0074709 (Dulcoside A)

3D Structure for NP0074709 (Dulcoside A)