NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate (NP0222964)

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Record Information

Version

2.0

Created at

2022-09-06 00:55:56 UTC

Updated at

2022-09-06 00:55:56 UTC

NP-MRD ID

NP0222964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

Description

(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1S,4S,5R,9R,10R,11S,13S,14S)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]Heptadecane-5-carboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate is found in Stevia subpubescens. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1S,4S,5R,9R,10R,11S,13S,14S)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]Heptadecane-5-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202552D          

 56 63  0  0  1  0            999 V2000
   -0.8088    0.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100    0.0365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3896    0.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.6386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7102    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377    1.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.8524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8662    0.8931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6830    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    2.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    0.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1810   -0.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4206   -0.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -1.2425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5572   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -2.3811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749   -1.7409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8719   -2.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7353   -1.4209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3927   -1.9193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897   -2.7379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5293   -3.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263   -3.8765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6659   -4.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086   -3.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837   -4.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9807   -5.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441   -4.0549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5015   -4.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9471   -3.2364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7075   -2.9163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8383   -0.6023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5987   -0.2823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017    0.5363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0443    1.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473    1.8533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4900    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930    3.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9077    2.1734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0107    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5651    1.6749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3255    1.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4621    0.8564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1195    0.3579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3134    0.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367   -0.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1127   -0.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654    0.1184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3405   -0.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5056   -0.8608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7953   -1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735   -0.7499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6484    0.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526   -0.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
 20 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
  8 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
  7 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 51  4  1  6  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 54 53  1  1  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
  4 55  1  0  0  0  0
 52 56  1  1  0  0  0
  2 56  1  0  0  0  0
M  END


  Mrv1652309062202552D          

 56 63  0  0  1  0            999 V2000
   -0.8088    0.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100    0.0365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3896    0.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.6386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7102    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377    1.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.8524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8662    0.8931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6830    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    2.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    0.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1810   -0.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4206   -0.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -1.2425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5572   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -2.3811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749   -1.7409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8719   -2.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7353   -1.4209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3927   -1.9193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897   -2.7379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5293   -3.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263   -3.8765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6659   -4.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086   -3.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837   -4.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9807   -5.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441   -4.0549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5015   -4.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9471   -3.2364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7075   -2.9163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8383   -0.6023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5987   -0.2823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017    0.5363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0443    1.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473    1.8533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4900    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930    3.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9077    2.1734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0107    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5651    1.6749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3255    1.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4621    0.8564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1195    0.3579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3134    0.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367   -0.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1127   -0.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654    0.1184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3405   -0.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5056   -0.8608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7953   -1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735   -0.7499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6484    0.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526   -0.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
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 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
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 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
 20 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
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 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
  8 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
  7 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 51  4  1  6  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 54 53  1  1  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
  4 55  1  0  0  0  0
 52 56  1  1  0  0  0
  2 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@]34C[C@H]1C[C@H](O2)[C@H]3[C@]1(C)CCC[C@](C)([C@H]1CC4)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H60O18/c1-35-6-4-7-36(2,20(35)5-8-38-10-15-9-16(30(35)38)56-37(15,3)14-38)34(49)55-33-29(54-32-27(48)25(46)22(43)18(12-40)51-32)28(23(44)19(13-41)52-33)53-31-26(47)24(45)21(42)17(11-39)50-31/h15-33,39-48H,4-14H2,1-3H3/t15-,16+,17-,18-,19-,20+,21-,22-,23-,24+,25+,26-,27-,28+,29-,30+,31+,32+,33+,35-,36-,37+,38+/m1/s1

> <INCHI_KEY>
PRRFBKXVIYXVGD-ITHMVSKESA-N

> <FORMULA>
C38H60O18

> <MOLECULAR_WEIGHT>
804.88

> <EXACT_MASS>
804.377965092

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
83.08557601923641

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1S,4S,5R,9R,10R,11S,13S,14S)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1^{11,14}.0^{1,10}.0^{4,9}]heptadecane-5-carboxylate

> <JCHEM_LOGP>
-2.116531258999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.367879616914998

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.879159706192072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98110113006672

> <JCHEM_POLAR_SURFACE_AREA>
283.97999999999996

> <JCHEM_REFRACTIVITY>
184.60840000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1S,4S,5R,9R,10R,11S,13S,14S)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1^{11,14}.0^{1,10}.0^{4,9}]heptadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.510   0.258   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.019   0.068   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.727   1.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   1.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.192   2.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.737   2.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.679   1.591   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.217   1.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.875   3.169   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.636   2.265   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.829   3.793   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.863   1.334   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.671  -0.194   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.252  -0.791   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.059  -2.319   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.640  -2.917   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.448  -4.445   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.287  -3.250   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.094  -4.778   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.706  -2.652   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.933  -3.583   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.741  -5.111   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.321  -5.708   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.129  -7.236   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.710  -7.834   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.483  -6.903   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.356  -8.167   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.164  -9.695   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.776  -7.569   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.003  -8.500   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.968  -6.041   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.387  -5.444   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.898  -1.124   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.318  -0.527   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.510   1.001   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.283   1.932   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.475   3.460   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.248   4.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.440   5.918   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.894   4.057   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.087   5.585   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      14.122   3.126   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      15.541   3.724   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      13.929   1.599   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      15.156   0.668   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.052   0.373   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.348  -0.997   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.810  -1.073   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.976   0.221   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.369  -1.194   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.391  -0.081   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.810  -1.607   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.484  -2.534   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.324  -1.400   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.210   0.097   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       1.405  -0.974   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   54   56                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   51   55                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   49                                                  
CONECT    8    7    9   10   46                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   13   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   44                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   35   45                                                  
CONECT   45   44                                                            
CONECT   46    8   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48    7   50   51                                             
CONECT   50   49                                                            
CONECT   51   49    4   52                                                  
CONECT   52   51   53   56                                                  
CONECT   53   52   54                                                       
CONECT   54   53    2   55                                                  
CONECT   55   54    4                                                       
CONECT   56   52    2                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  126    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-5-Hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1S,4S,5R,9R,10R,11S,13S,14S)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1,.0,.0,]heptadecane-5-carboxylic acid	Generator

Chemical Formula

C₃₈H₆₀O₁₈

Average Mass

804.8800 Da

Monoisotopic Mass

804.37797 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@]34C[C@H]1C[C@H](O2)[C@H]3[C@]1(C)CCC[C@](C)([C@H]1CC4)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C38H60O18/c1-35-6-4-7-36(2,20(35)5-8-38-10-15-9-16(30(35)38)56-37(15,3)14-38)34(49)55-33-29(54-32-27(48)25(46)22(43)18(12-40)51-32)28(23(44)19(13-41)52-33)53-31-26(47)24(45)21(42)17(11-39)50-31/h15-33,39-48H,4-14H2,1-3H3/t15-,16+,17-,18-,19-,20+,21-,22-,23-,24+,25+,26-,27-,28+,29-,30+,31+,32+,33+,35-,36-,37+,38+/m1/s1

InChI Key

PRRFBKXVIYXVGD-ITHMVSKESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stevia subpubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Oligosaccharide
Diterpenoid
Kaurane diterpenoid
Naphthopyran
Glycosyl compound
O-glycosyl compound
Naphthalene
Oxepane
Oxane
Pyran
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
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	-2.1	ChemAxon
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	283.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	184.61 m³·mol⁻¹	ChemAxon
Polarizability	83.09 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

163073596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate (NP0222964)

MOL for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D MOL for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D SDF for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D-SDF for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

PDB for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D PDB for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

SMILES for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

INCHI for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

Structure for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D Structure for NP0222964 ((2s,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl (1s,4s,5r,9r,10r,11s,13s,14s)-5,9,13-trimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)