NP-MRD: Showing NP-Card for withalongolide h (NP0265727)

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Record Information

Version

2.0

Created at

2022-09-08 09:48:55 UTC

Updated at

2022-09-08 09:48:55 UTC

NP-MRD ID

NP0265727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withalongolide h

Description

Withalongolide H belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. withalongolide h is found in Physalis longifolia. withalongolide h was first documented in 2012 (PMID: 24098060). Based on a literature review very few articles have been published on withalongolide H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211482D          

 55 62  0  0  1  0            999 V2000
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7837    3.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6009    2.9425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1073    3.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9245    3.4809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4309    4.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2481    4.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2354    2.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0527    2.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3635    1.8397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8572    1.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1681    0.4242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6617   -0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9853    0.3114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2962   -0.4528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4917    0.9627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.3089    0.8498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1808    1.7269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6871    2.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7291    2.0654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0399    1.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9118    2.1783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4055    1.5270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  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  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  6  0  0  0
 33 31  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 41 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 41 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 37 50  1  0  0  0  0
 50 51  1  1  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 36 53  1  0  0  0  0
 33 53  1  0  0  0  0
 53 54  1  1  0  0  0
 30 55  1  0  0  0  0
  2 55  1  0  0  0  0
M  END

     RDKit          3D

113120  0  0  0  0  0  0  0  0999 V2000
    2.1313    0.6402   -0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6333   -2.8943   -1.7899 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2465   -3.7052   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1607   -3.0903    0.0655 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183   -1.5651   -1.4678 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3818   -1.7326   -0.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4408    2.4961   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0452    0.7835   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253    1.8739   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465    2.7400   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    1.4624    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 41 40  1  6
 41 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
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 46 48  1  0
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 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  6
 31 30  1  0
 30 55  1  0
 55  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
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 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
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 23 24  1  0
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 25 26  1  0
  3 27  1  0
 27 28  2  0
 27 29  1  0
 53 33  1  0
 29 30  1  0
 53 36  1  0
 25  6  1  0
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 21 13  1  0
 41 39  1  0
 48 41  1  0
 32 84  1  0
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 32 86  1  0
 31 83  1  1
 33 87  1  1
 34 88  1  0
 34 89  1  0
 35 90  1  0
 35 91  1  0
 36 92  1  1
 37 93  1  6
 38 94  1  0
 38 95  1  0
 39 96  1  1
 42 97  1  1
 43 98  1  0
 44 99  1  0
 45100  1  0
 49101  1  0
 49102  1  0
 49103  1  0
 50104  1  1
 51105  1  0
 51106  1  0
 52107  1  0
 52108  1  0
 54109  1  0
 54110  1  0
 54111  1  0
 30 82  1  6
 55112  1  0
 55113  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  4 59  1  0
  4 60  1  0
  6 61  1  6
  8 62  1  6
  9 63  1  0
  9 64  1  0
 10 65  1  0
 11 66  1  1
 13 67  1  1
 15 68  1  6
 16 69  1  0
 16 70  1  0
 16 71  1  0
 17 72  1  1
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 20 75  1  0
 21 76  1  1
 22 77  1  0
 23 78  1  6
 24 79  1  0
 25 80  1  6
 26 81  1  0
M  END


  Mrv1652309082211482D          

 55 62  0  0  1  0            999 V2000
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7837    3.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6009    2.9425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1073    3.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9245    3.4809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4309    4.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2481    4.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2354    2.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0527    2.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3635    1.8397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8572    1.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1681    0.4242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6617   -0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9853    0.3114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2962   -0.4528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4917    0.9627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.3089    0.8498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1808    1.7269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6871    2.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7291    2.0654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0399    1.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9118    2.1783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4055    1.5270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  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  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  6  0  0  0
 33 31  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 41 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 41 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 37 50  1  0  0  0  0
 50 51  1  1  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 36 53  1  0  0  0  0
 33 53  1  0  0  0  0
 53 54  1  1  0  0  0
 30 55  1  0  0  0  0
  2 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265727

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC(C)=C(CO[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]2O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C40H58O15/c1-16-12-24(17(2)21-6-7-22-19-13-28-40(55-28)27(43)9-8-26(42)39(40,5)23(19)10-11-38(21,22)4)52-35(49)20(16)15-50-36-33(48)31(46)34(25(14-41)53-36)54-37-32(47)30(45)29(44)18(3)51-37/h8-9,17-19,21-25,27-34,36-37,41,43-48H,6-7,10-15H2,1-5H3/t17-,18-,19-,21+,22-,23-,24+,25+,27-,28+,29-,30+,31+,32+,33+,34+,36+,37-,38+,39-,40+/m0/s1

> <INCHI_KEY>
KWSCHTSFNFDQSG-IPAGGVPOSA-N

> <FORMULA>
C40H58O15

> <MOLECULAR_WEIGHT>
778.889

> <EXACT_MASS>
778.377571168

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
83.33304882087147

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <JCHEM_LOGP>
1.0872127896666677

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.465974618017306

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.933435684083895

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9813780697565635

> <JCHEM_POLAR_SURFACE_AREA>
234.42999999999998

> <JCHEM_REFRACTIVITY>
190.47760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      16.157   7.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.792   4.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.318   4.487   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      18.263   5.703   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      19.788   5.493   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      20.734   6.708   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.259   6.498   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.204   7.714   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.730   7.503   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      22.839   5.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.365   4.861   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.945   3.434   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.000   2.218   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      24.580   0.792   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.635  -0.424   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.106   0.581   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.686  -0.845   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      27.051   1.797   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.577   1.586   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      26.471   3.224   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      27.416   4.439   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      21.894   3.855   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.475   2.429   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.369   4.066   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      19.424   2.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.847   3.482   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.427   2.056   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.321   3.693   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   55                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
CONECT   23   11   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25                                                            
CONECT   27    3   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   55                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   53                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   53                                                  
CONECT   37   36   38   50                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39   41                                                       
CONECT   41   40   39   42   48                                             
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   41   49   50                                             
CONECT   49   48                                                            
CONECT   50   48   37   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   36   33   54                                             
CONECT   54   53                                                            
CONECT   55   30    2                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  124    0
END

View in JSmol

Synonyms

Value	Source
27-O-[alpha-L-Rhamnopyranosyl(1->4)]-beta-D-glucopyranosylwithaferin a	ChEBI
27-O-[a-L-Rhamnopyranosyl(1->4)]-b-D-glucopyranosylwithaferin a	Generator
27-O-[Α-L-rhamnopyranosyl(1->4)]-β-D-glucopyranosylwithaferin a	Generator

Chemical Formula

C₄₀H₅₈O₁₅

Average Mass

778.8890 Da

Monoisotopic Mass

778.37757 Da

IUPAC Name

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

Traditional Name

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC(C)=C(CO[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]2O)C(=O)O1

InChI Identifier

InChI=1S/C40H58O15/c1-16-12-24(17(2)21-6-7-22-19-13-28-40(55-28)27(43)9-8-26(42)39(40,5)23(19)10-11-38(21,22)4)52-35(49)20(16)15-50-36-33(48)31(46)34(25(14-41)53-36)54-37-32(47)30(45)29(44)18(3)51-37/h8-9,17-19,21-25,27-34,36-37,41,43-48H,6-7,10-15H2,1-5H3/t17-,18-,19-,21+,22-,23-,24+,25+,27-,28+,29-,30+,31+,32+,33+,34+,36+,37-,38+,39-,40+/m0/s1

InChI Key

KWSCHTSFNFDQSG-IPAGGVPOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Physalis longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroidal glycoside
5,6-epoxysteroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Oxepane
Cyclohexenone
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Dialkyl ether
Monocarboxylic acid or derivatives
Ether
Oxirane
Acetal
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:69112 )
delta-lactone (CHEBI:69112 )
4-hydroxy steroid (CHEBI:69112 )
ergostanoid (CHEBI:69112 )
withanolide saponin (CHEBI:69112 )

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	1.09	ChemAxon
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	234.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	190.48 m³·mol⁻¹	ChemAxon
Polarizability	83.33 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

28492219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56649370

PDB ID

Not Available

ChEBI ID

69112

Good Scents ID

Not Available

References

General References

Zhang H, Samadi AK, Cohen MS, Timmermann BN: Anti-proliferative withanolides from the Solanaceae: a structure-activity study. Pure Appl Chem. 2012;84(6):1353-1367. doi: 10.1351/PAC-CON-11-10-08. [PubMed:24098060 ]
LOTUS database [Link]

Showing NP-Card for withalongolide h (NP0265727)

MOL for NP0265727 (withalongolide h)

3D MOL for NP0265727 (withalongolide h)

3D SDF for NP0265727 (withalongolide h)

3D-SDF for NP0265727 (withalongolide h)

PDB for NP0265727 (withalongolide h)

3D PDB for NP0265727 (withalongolide h)

SMILES for NP0265727 (withalongolide h)

INCHI for NP0265727 (withalongolide h)

Structure for NP0265727 (withalongolide h)

3D Structure for NP0265727 (withalongolide h)