NP-MRD: Showing NP-Card for Rebaudioside E (NP0074766)

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Record Information

Version

2.0

Created at

2022-04-28 20:05:41 UTC

Updated at

2022-04-28 20:05:41 UTC

NP-MRD ID

NP0074766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rebaudioside E

Description

(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (1R,4S,5S,9R,10S,13S)-13-{[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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. Rebaudioside E is found in Stevia rebaudiana . Based on a literature review very few articles have been published on (2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (1R,4S,5S,9R,10S,13S)-13-{[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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


  Mrv1652304282222052D          

 67 74  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  2  0  0  0  0  0  0  0  0  0
    1.9555    0.9995    0.0000 C   0  0  2  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
   -0.4225    3.1929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755    4.0166    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
   -1.8021    4.0980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8491    3.2744    0.0000 C   0  0  2  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
   -4.5613    5.9082    0.0000 O   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
   -2.4919    4.5506    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
    0.3613    4.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    5.2113    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
    3.3930   -1.3416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -0.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826   -0.8992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7767   -1.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657   -2.2758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1605   -2.0547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3663   -1.2558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7774   -0.6780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9832    0.1209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7780    0.3421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9839    1.1410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7787    1.3621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3676    0.7844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1618   -0.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3670   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7507   -0.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5455   -0.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1624    1.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9845    2.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949    1.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611   -1.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494   -2.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598   -3.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7487   -3.6525    0.0000 O   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
  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  1  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  6  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
 24 25  1  1  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 29 34  1  1  0  0  0
 28 35  1  6  0  0  0
 27 36  1  1  0  0  0
 23 37  1  6  0  0  0
 22 38  1  1  0  0  0
 21 39  1  6  0  0  0
 39 40  1  0  0  0  0
  5 41  1  6  0  0  0
  3 42  1  6  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 45 44  1  1  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  6  0  0  0
 52 51  1  1  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 52 57  1  0  0  0  0
 56 58  1  1  0  0  0
 58 59  1  0  0  0  0
 55 60  1  1  0  0  0
 54 61  1  1  0  0  0
 53 62  1  6  0  0  0
 49 63  1  1  0  0  0
 48 64  1  1  0  0  0
 47 65  1  6  0  0  0
 65 66  1  0  0  0  0
  3 67  1  1  0  0  0
M  END

     RDKit          3D

137144  0  0  0  0  0  0  0  0999 V2000
   -4.5669    0.7294   -1.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455    0.3565   -0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -0.5623   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -0.2219   -0.5549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2520   -1.2589   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411   -0.6861   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506    0.2510   -1.5313 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7917    0.9310   -1.4215 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0032    1.7522   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -0.1275   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006   -0.2591   -2.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356   -1.0054   -0.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180   -1.9998   -0.4068 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3580   -3.2194   -0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539   -4.3277   -0.4174 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9247   -4.9444   -1.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7106   -6.0790   -1.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6212   -4.0214   -0.2902 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2945   -5.2246   -0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7613   -3.1147    0.9243 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2702   -3.8134    2.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393   -1.8003    0.6941 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9860   -0.9034    0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0588    0.2756    0.9573 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.6262    2.1302   -0.3403 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3155    1.4139   -1.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3763    1.1158   -2.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8504    2.6924    0.0766 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5766    1.9083    1.9601 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8350    2.0966    2.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2666   -0.1997    2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9896    2.8723   -2.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7218   -0.6245    1.5113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2667   -1.0959    2.7788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952   -2.4805    2.8241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4831   -2.9050    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5724   -2.3415    4.9190 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6567   -2.0568    1.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6448   -2.1813    2.7483 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1995    2.2998    0.4149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0808    2.8537   -0.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5395    4.1169   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5311    1.8529   -1.4805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1445    2.4017   -2.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4860    0.9138   -0.7469 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4783   -0.2931   -1.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0510    0.7937    0.7063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8870    1.6088    1.4556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0132   -0.1359    0.8072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058    0.3866   -2.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3308    1.4240   -1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -0.5963   -2.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097   -1.5954   -1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.7235   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006   -2.1083    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5434   -0.4089   -2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2058    2.8255   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115    1.7545    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    1.4591    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5615   -1.9394   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282222052D          

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M  END
> <DATABASE_ID>
NP0074766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC[C@@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@H]23)O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O)C(=O)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-34(30(55)26(51)20(14-47)62-38)64-36-32(57)28(53)24(49)18(12-45)60-36)23(43)6-10-44(17,16-43)67-39-35(31(56)27(52)21(15-48)63-39)65-37-33(58)29(54)25(50)19(13-46)61-37/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19+,20+,21+,22+,23-,24+,25+,26+,27+,28+,29-,30+,31-,32-,33+,34-,35+,36+,37-,38+,39-,41+,42+,43-,44+/m1/s1

> <INCHI_KEY>
RLLCWNUIHGPAJY-RYBZXKSASA-N

> <FORMULA>
C44H70O23

> <MOLECULAR_WEIGHT>
967.021

> <EXACT_MASS>
966.430788514

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
137

> <JCHEM_AVERAGE_POLARIZABILITY>
97.71486932186102

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (1R,4S,5S,9R,10S,13S)-13-{[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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>
-1.43

> <JCHEM_LOGP>
-3.9320440309999984

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.28980738317329

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.841370168477596

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486749316154388

> <JCHEM_POLAR_SURFACE_AREA>
374.13000000000005

> <JCHEM_REFRACTIVITY>
218.56280000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl (1R,4S,5S,9R,10S,13S)-13-{[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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  O   UNK     0      -0.789   5.960   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.701   7.498   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      -3.364   7.650   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.452   6.112   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.827   5.419   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.115   6.264   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.490   5.571   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.778   6.416   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.690   7.954   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.315   8.646   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.027   7.802   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -7.227  10.184   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.514  11.029   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.978   8.798   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -10.153   5.723   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -7.578   4.034   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -4.652   8.494   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.901   9.880   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.674   8.190   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.762   9.728   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.334  -2.504   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.201  -0.600   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       9.301  -1.679   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.917  -3.170   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      10.016  -4.248   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.500  -3.835   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.884  -2.344   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.784  -1.266   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      11.169   0.226   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.652   0.638   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.037   2.130   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.520   2.543   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      15.620   1.464   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      15.235  -0.027   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      13.752  -0.440   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      16.335  -1.105   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      17.818  -0.693   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      17.103   1.877   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      14.904   4.034   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      11.937   3.208   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      13.367  -1.931   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      12.599  -4.914   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       9.632  -5.740   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      10.731  -6.818   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   42   67                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   41                                             
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                                                       
CONECT   21   20   22   39                                                  
CONECT   22   21   23   38                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
CONECT   37   23                                                            
CONECT   38   22                                                            
CONECT   39   21   40                                                       
CONECT   40   39                                                            
CONECT   41    5                                                            
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   65                                                  
CONECT   48   47   49   64                                                  
CONECT   49   48   50   63                                                  
CONECT   50   49   45   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   57                                                  
CONECT   53   52   54   62                                                  
CONECT   54   53   55   61                                                  
CONECT   55   54   56   60                                                  
CONECT   56   55   57   58                                                  
CONECT   57   56   52                                                       
CONECT   58   56   59                                                       
CONECT   59   58                                                            
CONECT   60   55                                                            
CONECT   61   54                                                            
CONECT   62   53                                                            
CONECT   63   49                                                            
CONECT   64   48                                                            
CONECT   65   47   66                                                       
CONECT   66   65                                                            
CONECT   67    3                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₄H₇₀O₂₃

Average Mass

967.0210 Da

Monoisotopic Mass

966.43079 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@]12CCC[C@@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@H]23)O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O)C(=O)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-34(30(55)26(51)20(14-47)62-38)64-36-32(57)28(53)24(49)18(12-45)60-36)23(43)6-10-44(17,16-43)67-39-35(31(56)27(52)21(15-48)63-39)65-37-33(58)29(54)25(50)19(13-46)61-37/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19+,20+,21+,22+,23-,24+,25+,26+,27+,28+,29-,30+,31-,32-,33+,34-,35+,36+,37-,38+,39-,41+,42+,43-,44+/m1/s1

InChI Key

RLLCWNUIHGPAJY-RYBZXKSASA-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	-1.4	ALOGPS
logP	-3.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	374.13 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	218.56 m³·mol⁻¹	ChemAxon
Polarizability	97.71 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154497343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rebaudioside E (NP0074766)

MOL for NP0074766 (Rebaudioside E)

3D MOL for NP0074766 (Rebaudioside E)

3D SDF for NP0074766 (Rebaudioside E)

3D-SDF for NP0074766 (Rebaudioside E)

PDB for NP0074766 (Rebaudioside E)

3D PDB for NP0074766 (Rebaudioside E)

SMILES for NP0074766 (Rebaudioside E)

INCHI for NP0074766 (Rebaudioside E)

Structure for NP0074766 (Rebaudioside E)

3D Structure for NP0074766 (Rebaudioside E)