NP-MRD: Showing NP-Card for Astragaloside I (NP0083013)

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Record Information

Version

2.0

Created at

2022-04-29 04:04:15 UTC

Updated at

2022-04-29 04:04:15 UTC

NP-MRD ID

NP0083013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Astragaloside I

Description

(2R,3R,4S,5S)-4-(acetyloxy)-5-hydroxy-2-{[(1S,3R,6R,8S,9R,11S,12R,14S,15S,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}oxan-3-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Astragaloside I is found in Astragalus icmadophilus, Astragalus membranaceus , Astragalus microcephalus and Astragalus sieversianus. Based on a literature review very few articles have been published on (2R,3R,4S,5S)-4-(acetyloxy)-5-hydroxy-2-{[(1S,3R,6R,8S,9R,11S,12R,14S,15S,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}oxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206042D          

 61 68  0  0  1  0            999 V2000
    4.0480    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2995    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1116    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3919    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8601    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4458    0.1741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7629   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2217   -0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0827    2.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8999    2.2474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0451    1.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3176    1.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4716    2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0432    3.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8768    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0664    2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0221    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -0.8489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6752   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9555    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4237    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8631   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513   -0.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -1.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8248    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3566    1.2383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0763    2.0142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2642    2.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677    1.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081    2.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687    1.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126    1.5785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202    2.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051   -0.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5732   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -0.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9268   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -2.2555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1783   -3.0315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7101   -3.6622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5222   -3.5170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8025   -2.7410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2707   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0540   -4.1477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298   -4.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -3.1767    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
  4  9  1  0  0  0  0
  8 10  1  1  0  0  0
  7 11  1  6  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 11 20  1  1  0  0  0
  5 21  1  1  0  0  0
  4 22  1  1  0  0  0
  3 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
  2 26  1  0  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
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  6  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  1  0  0  0
 36 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 35 45  1  6  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 26 49  1  1  0  0  0
  2 49  1  1  0  0  0
 24 50  1  1  0  0  0
 51 50  1  6  0  0  0
 51 52  1  0  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
 51 56  1  0  0  0  0
 55 57  1  6  0  0  0
 57 58  1  0  0  0  0
 54 59  1  1  0  0  0
 53 60  1  6  0  0  0
 52 61  1  1  0  0  0
M  END

     RDKit          3D

133140  0  0  0  0  0  0  0  0999 V2000
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   -9.3470   -2.0196    1.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2879   -1.6122    3.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1998   -2.5731    1.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0358   -2.6548    2.0721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6165   -4.1339    2.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6312   -4.7044    0.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1875   -4.2287    2.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -2.9798    3.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5969   -2.1040    1.9367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9301   -0.9594    2.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6289   -0.8594    1.8487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6556   -0.9777    3.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2811   -0.6060    2.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285   -0.8458    1.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.7296    0.6410   -1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8589   -1.1076   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4711    1.0269   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339    0.6885    2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4055   -1.0590    2.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9386   -0.1999    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7421    0.9038    0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5897   -0.6444    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0770   -2.4857    1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355    1.0563   -1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5053   -0.2894   -4.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8160   -0.7607   -3.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2031   -1.2561   -1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6511    1.3616   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    1.6690    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0677    5.3083    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4027    7.5400   -2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9193    5.0202   -3.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687    3.7485   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4508    3.4603   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748    5.3035   -1.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0
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 13 14  1  0
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 20 21  1  1
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 33 34  1  0
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 42112  1  1
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 31100  1  0
 57130  1  6
 60131  1  0
 60132  1  0
 60133  1  0
M  END


  Mrv1652304292206042D          

 61 68  0  0  1  0            999 V2000
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    0.2389   -0.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9268   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -2.2555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.7101   -3.6622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5222   -3.5170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8025   -2.7410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2707   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  1  6  1  0  0  0  0
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  4  9  1  0  0  0  0
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 16 17  1  0  0  0  0
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 16 19  1  0  0  0  0
 11 20  1  1  0  0  0
  5 21  1  1  0  0  0
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 24 25  1  0  0  0  0
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  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 25 30  1  0  0  0  0
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 29 33  1  6  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  1  0  0  0
 36 41  1  1  0  0  0
 41 42  1  0  0  0  0
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 45 46  1  0  0  0  0
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  2 49  1  1  0  0  0
 24 50  1  1  0  0  0
 51 50  1  6  0  0  0
 51 52  1  0  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
 51 56  1  0  0  0  0
 55 57  1  6  0  0  0
 57 58  1  0  0  0  0
 54 59  1  1  0  0  0
 53 60  1  6  0  0  0
 52 61  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](O)CO[C@H](O[C@@H]2CC[C@]34C[C@]33CC[C@]5(C)[C@@H]([C@@H](O)C[C@]5(C)[C@@H]3C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]4C2(C)C)[C@@]2(C)CC[C@@H](O2)C(C)(C)O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C45H72O16/c1-21(47)56-33-24(50)19-55-38(34(33)57-22(2)48)60-28-11-13-45-20-44(45)15-14-41(7)35(43(9)12-10-29(61-43)40(5,6)54)23(49)17-42(41,8)27(44)16-25(36(45)39(28,3)4)58-37-32(53)31(52)30(51)26(18-46)59-37/h23-38,46,49-54H,10-20H2,1-9H3/t23-,24-,25+,26+,27-,28+,29+,30+,31-,32+,33-,34+,35+,36+,37+,38+,41+,42+,43+,44-,45+/m0/s1

> <INCHI_KEY>
KXHCYYSIAXMSPA-JZRBLOCISA-N

> <FORMULA>
C45H72O16

> <MOLECULAR_WEIGHT>
869.055

> <EXACT_MASS>
868.482036238

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
133

> <JCHEM_AVERAGE_POLARIZABILITY>
92.1850671873514

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S)-4-(acetyloxy)-5-hydroxy-2-{[(1S,3R,6R,8S,9R,11S,12R,14S,15S,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}oxan-3-yl acetate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
0.5707077903333346

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.959259626437813

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.172585830604067

> <JCHEM_PKA_STRONGEST_BASIC>
-2.87594324507326

> <JCHEM_POLAR_SURFACE_AREA>
240.35999999999996

> <JCHEM_REFRACTIVITY>
212.8831

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S)-4-(acetyloxy)-5-hydroxy-2-{[(1S,3R,6R,8S,9R,11S,12R,14S,15S,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.556   2.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.033   1.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.026   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.542   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.065   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.072   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.604   1.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.032   0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.757  -0.539   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.480  -0.198   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.549   3.020   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.221   4.406   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.747   4.195   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.018   2.679   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.660   1.953   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.814   5.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.881   6.416   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.703   6.373   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.924   4.238   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.241   3.833   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.737   3.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.173  -1.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.502  -1.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.986  -1.585   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.994  -0.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.517   1.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.524   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.008   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.485   0.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.478  -0.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.336  -1.712   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.696  -2.203   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.969   0.228   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.024   1.405   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.540   1.134   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.532   2.311   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.009   3.760   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.493   4.031   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.500   2.854   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.002   4.937   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.048   2.040   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -5.041   3.218   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -6.557   2.947   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -4.518   4.666   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -2.063  -0.314   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.070  -1.492   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.446  -1.221   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.593  -2.940   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.040   2.489   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       5.463  -3.033   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       6.456  -4.210   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.933  -5.659   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       6.926  -6.836   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.441  -6.565   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.965  -5.117   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       7.972  -3.939   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      10.481  -4.846   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      11.004  -3.397   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       9.434  -7.742   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       6.402  -8.284   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       4.417  -5.930   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26   49                                             
CONECT    3    2    4   23                                                  
CONECT    4    3    5    9   22                                             
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8                                                            
CONECT   11    7   12   15   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16   13   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   11                                                            
CONECT   21    5                                                            
CONECT   22    4                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   50                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25    2   27   49                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   25   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36   45                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   37                                                            
CONECT   41   36   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   35   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   26    2                                                       
CONECT   50   24   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   53   61                                                  
CONECT   53   52   54   60                                                  
CONECT   54   53   55   59                                                  
CONECT   55   54   56   57                                                  
CONECT   56   55   51                                                       
CONECT   57   55   58                                                       
CONECT   58   57                                                            
CONECT   59   54                                                            
CONECT   60   53                                                            
CONECT   61   52                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,5S)-4-(Acetyloxy)-5-hydroxy-2-{[(1S,3R,6R,8S,9R,11S,12R,14S,15S,16R)-14-hydroxy-15-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentacyclo[9.7.0.0,.0,.0,]octadecan-6-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₄₅H₇₂O₁₆

Average Mass

869.0550 Da

Monoisotopic Mass

868.48204 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](O)CO[C@H](O[C@@H]2CC[C@]34C[C@]33CC[C@]5(C)[C@@H]([C@@H](O)C[C@]5(C)[C@@H]3C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]4C2(C)C)[C@@]2(C)CC[C@@H](O2)C(C)(C)O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C45H72O16/c1-21(47)56-33-24(50)19-55-38(34(33)57-22(2)48)60-28-11-13-45-20-44(45)15-14-41(7)35(43(9)12-10-29(61-43)40(5,6)54)23(49)17-42(41,8)27(44)16-25(36(45)39(28,3)4)58-37-32(53)31(52)30(51)26(18-46)59-37/h23-38,46,49-54H,10-20H2,1-9H3/t23-,24-,25+,26+,27-,28+,29+,30+,31-,32+,33-,34+,35+,36+,37+,38+,41+,42+,43+,44-,45+/m0/s1

InChI Key

KXHCYYSIAXMSPA-JZRBLOCISA-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
Astragalus icmadophilus	LOTUS Database	35616633
Astragalus membranaceus	Plant	KNApSAcK
Astragalus microcephalus	Plant	KNApSAcK
Astragalus sieversianus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
16-hydroxysteroid
16-beta-hydroxysteroid
Hydroxysteroid
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
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	1.65	ALOGPS
logP	0.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	240.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	212.88 m³·mol⁻¹	ChemAxon
Polarizability	92.19 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

154496212

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Astragaloside I (NP0083013)

MOL for NP0083013 (Astragaloside I)

3D MOL for NP0083013 (Astragaloside I)

3D SDF for NP0083013 (Astragaloside I)

3D-SDF for NP0083013 (Astragaloside I)

PDB for NP0083013 (Astragaloside I)

3D PDB for NP0083013 (Astragaloside I)

SMILES for NP0083013 (Astragaloside I)

INCHI for NP0083013 (Astragaloside I)

Structure for NP0083013 (Astragaloside I)

3D Structure for NP0083013 (Astragaloside I)