NP-MRD: Showing NP-Card for Cimicifugoside (NP0052069)

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Record Information

Version

2.0

Created at

2022-04-27 23:14:38 UTC

Updated at

2022-04-27 23:14:38 UTC

NP-MRD ID

NP0052069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cimicifugoside

Description

(1S,1'S,2S,3'R,4S,4'R,5R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-4-hydroxy-4',5,6',12',17',17'-hexamethyl-18'-{[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,6,9'-trioxaspiro[bicyclo[3.1.0]Hexane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan]-13'-en-3'-yl acetate belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. Cimicifugoside is found in Cimicifuga simplex and Cimicifuga spp.. Based on a literature review very few articles have been published on (1S,1'S,2S,3'R,4S,4'R,5R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-4-hydroxy-4',5,6',12',17',17'-hexamethyl-18'-{[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,6,9'-trioxaspiro[bicyclo[3.1.0]Hexane-2,8'-hexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan]-13'-en-3'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201142D          

 48 56  0  0  1  0            999 V2000
   -0.6069   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -1.0712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1805   -1.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069   -1.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7874   -0.5788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1805   -0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -0.3326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1817   -0.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138   -1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -0.6452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1496    0.1598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5427    0.7186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7553    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163    2.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    1.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2968    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9710    0.2369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2982   -0.5204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1176   -0.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6100    0.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2828    0.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4633    0.8989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1362    1.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1688    0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9187    0.3092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8233   -0.5102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0145   -0.6728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5597   -1.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6283   -0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6377    0.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790   -1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -1.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -2.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1817   -0.7586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9691   -1.0048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5761   -0.4460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3956    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6082    0.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0012    0.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0025    0.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3635   -0.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496   -1.8098    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  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 12  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 22 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 30  1  0  0  0  0
 28 31  1  1  0  0  0
 27 32  1  6  0  0  0
 20 33  1  1  0  0  0
 11 33  1  0  0  0  0
 12 34  1  1  0  0  0
 11 35  1  6  0  0  0
  7 36  1  1  0  0  0
  5 36  1  1  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  2 39  1  1  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 43 46  1  1  0  0  0
 42 47  1  6  0  0  0
 41 48  1  6  0  0  0
M  END

     RDKit          3D

102110  0  0  0  0  0  0  0  0999 V2000
   -2.6868   -1.1031   -5.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442   -0.0455   -4.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101    1.0997   -4.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228   -0.3016   -2.8512 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6058   -0.1820    0.6991 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0910   -1.1231    1.5995 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0961    2.1722    0.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965    0.6524    1.7959 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2046    1.6343    2.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9677    1.5535    2.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    0.5815    1.1841 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3480   -0.3079    2.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867    0.1120    2.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    0.3153    0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9841    0.7277    0.7160 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.9505    0.1860    1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3821   -1.2945    0.9705 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7802   -1.1086   -5.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38 37  1  0
 37 36  1  0
 36 35  1  0
 35 42  1  6
 42 43  1  0
 43 44  1  0
 43 45  1  0
 45 46  1  1
 45 47  1  0
 47 48  1  0
 35 34  1  0
 34 33  1  0
 33 32  1  0
 32 30  1  0
 30 31  1  6
 30 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  1  0
 26  9  1  0
  9  8  1  6
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 40  1  0
 40 41  1  1
 40 39  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 12 23  1  0
 23 24  1  1
 23 25  1  0
 39 37  1  0
 21 14  1  0
 48 35  1  0
 39 33  1  0
 48 45  1  0
 40 30  1  0
  7 29  1  0
 23 26  1  0
  7  9  1  0
 38 90  1  0
 38 91  1  0
 38 92  1  0
 37 89  1  6
 36 87  1  0
 36 88  1  0
 43 97  1  6
 44 98  1  0
 46 99  1  0
 46100  1  0
 46101  1  0
 48102  1  1
 33 86  1  1
 32 84  1  0
 32 85  1  0
 31 81  1  0
 31 82  1  0
 31 83  1  0
 28 80  1  0
 27 78  1  0
 27 79  1  0
 26 77  1  1
  8 55  1  0
  8 56  1  0
  6 53  1  0
  6 54  1  0
  5 52  1  6
  1 49  1  0
  1 50  1  0
  1 51  1  0
 41 94  1  0
 41 95  1  0
 41 96  1  0
 39 93  1  1
 10 57  1  0
 10 58  1  0
 11 59  1  0
 11 60  1  0
 12 61  1  6
 14 62  1  6
 16 63  1  0
 16 64  1  0
 17 65  1  6
 18 66  1  0
 19 67  1  1
 20 68  1  0
 21 69  1  1
 22 70  1  0
 24 71  1  0
 24 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 25 76  1  0
M  END


  Mrv1652304282201142D          

 48 56  0  0  1  0            999 V2000
   -0.6069   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -1.0712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1805   -1.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069   -1.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7874   -0.5788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1805   -0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -0.3326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1817   -0.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138   -1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -0.6452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1496    0.1598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5427    0.7186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7553    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163    2.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    1.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2968    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9710    0.2369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2982   -0.5204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1176   -0.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6100    0.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2828    0.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4633    0.8989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1362    1.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1688    0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9187    0.3092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8233   -0.5102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0145   -0.6728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5597   -1.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6283   -0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6377    0.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790   -1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -1.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -2.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1817   -0.7586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9691   -1.0048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5761   -0.4460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3956    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6082    0.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0012    0.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0025    0.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3635   -0.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496   -1.8098    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  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 12  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 22 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 30  1  0  0  0  0
 28 31  1  1  0  0  0
 27 32  1  6  0  0  0
 20 33  1  1  0  0  0
 11 33  1  0  0  0  0
 12 34  1  1  0  0  0
 11 35  1  6  0  0  0
  7 36  1  1  0  0  0
  5 36  1  1  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  2 39  1  1  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 43 46  1  1  0  0  0
 42 47  1  6  0  0  0
 41 48  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]2(O[C@H](O)[C@]3(C)O[C@H]23)O[C@H]2C[C@@]3(C)C4=CC[C@@H]5[C@]6(C[C@@]46C[C@@H](OC(C)=O)[C@]3(C)[C@@H]12)CC[C@H](O[C@@H]1OC[C@H](O)[C@@H](O)[C@H]1O)C5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H54O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h9,17,19-21,23-30,39-42H,8,10-16H2,1-7H3/t17-,19+,20+,21+,23+,24-,25+,26-,27-,28+,29+,30+,32+,33-,34-,35-,36+,37+/m1/s1

> <INCHI_KEY>
XUJMHSCMPCZWOV-SJHGIUISSA-N

> <FORMULA>
C37H54O11

> <MOLECULAR_WEIGHT>
674.828

> <EXACT_MASS>
674.366612559

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
74.38801757635338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,1'S,2S,3'R,4S,4'R,5R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-4-hydroxy-4',5,6',12',17',17'-hexamethyl-18'-{[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,6,9'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-hexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan]-13'-en-3'-yl acetate

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
2.343380624

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.274232090964063

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.072582623802328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806236668373

> <JCHEM_POLAR_SURFACE_AREA>
156.67000000000002

> <JCHEM_REFRACTIVITY>
168.92360000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'S,2S,3'R,4S,4'R,5R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-4-hydroxy-4',5,6',12',17',17'-hexamethyl-18'-{[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,6,9'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-hexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan]-13'-en-3'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.133  -0.497   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.470  -2.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.337  -3.043   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.133  -2.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.470  -1.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.337  -0.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.940  -0.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.073  -1.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.736  -3.167   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.266  -3.626   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.542  -1.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.879   0.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.746   1.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.277   0.882   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.083   2.844   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.950   3.887   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.481   3.428   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.287   5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.413   0.442   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.023  -0.971   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.553  -1.149   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.472   0.086   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.861   1.500   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.332   1.678   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.721   3.092   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.515   1.219   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.915   0.577   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.737  -0.952   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.227  -1.256   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.245  -2.412   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.240  -1.289   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.257   1.332   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.867  -1.989   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.371   1.758   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.364  -2.734   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.807   0.422   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.340  -4.211   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.071  -4.528   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.940  -2.459   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.073  -1.416   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.542  -1.876   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.675  -0.833   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.338   0.670   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.869   1.130   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -3.736   0.087   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -7.471   1.713   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -8.145  -1.292   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -5.879  -3.378   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4   37   38                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   36                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14   36                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   33   35                                             
CONECT   12   11   13   19   34                                             
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20   24                                                  
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26   29                                             
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28   22   30                                                  
CONECT   30   29   28                                                       
CONECT   31   28                                                            
CONECT   32   27                                                            
CONECT   33   20   11                                                       
CONECT   34   12                                                            
CONECT   35   11                                                            
CONECT   36    7    5                                                       
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    2   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42   48                                                  
CONECT   42   41   43   47                                                  
CONECT   43   42   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
CONECT   46   43                                                            
CONECT   47   42                                                            
CONECT   48   41                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  112    0
END

View in JSmol

Synonyms

Value	Source
(1S,1's,2S,3'r,4S,4'r,5R,5'r,6'r,10's,12's,16'r,18's,21'r)-4-Hydroxy-4',5,6',12',17',17'-hexamethyl-18'-{[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,6,9'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-hexacyclo[11.9.0.0,.0,.0,.0,]docosan]-13'-en-3'-yl acetic acid	Generator

Chemical Formula

C₃₇H₅₄O₁₁

Average Mass

674.8280 Da

Monoisotopic Mass

674.36661 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]2(O[C@H](O)[C@]3(C)O[C@H]23)O[C@H]2C[C@@]3(C)C4=CC[C@@H]5[C@]6(C[C@@]46C[C@@H](OC(C)=O)[C@]3(C)[C@@H]12)CC[C@H](O[C@@H]1OC[C@H](O)[C@@H](O)[C@H]1O)C5(C)C

InChI Identifier

InChI=1S/C37H54O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h9,17,19-21,23-30,39-42H,8,10-16H2,1-7H3/t17-,19+,20+,21+,23+,24-,25+,26-,27-,28+,29+,30+,32+,33-,34-,35-,36+,37+/m1/s1

InChI Key

XUJMHSCMPCZWOV-SJHGIUISSA-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
Actaea simplex	Plant	KNApSAcK
Cimicifuga spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Steroid ester
O-glycosyl compound
Glycosyl compound
Ketal
Oxane
Monosaccharide
Para-dioxane
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.3	ALOGPS
logP	2.34	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	156.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	168.92 m³·mol⁻¹	ChemAxon
Polarizability	74.39 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162991647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cimicifugoside (NP0052069)

MOL for NP0052069 (Cimicifugoside)

3D MOL for NP0052069 (Cimicifugoside)

3D SDF for NP0052069 (Cimicifugoside)

3D-SDF for NP0052069 (Cimicifugoside)

PDB for NP0052069 (Cimicifugoside)

3D PDB for NP0052069 (Cimicifugoside)

SMILES for NP0052069 (Cimicifugoside)

INCHI for NP0052069 (Cimicifugoside)

Structure for NP0052069 (Cimicifugoside)

3D Structure for NP0052069 (Cimicifugoside)