NP-MRD: Showing NP-Card for Khayanoside (NP0080268)

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Record Information

Version

2.0

Created at

2022-04-29 01:18:59 UTC

Updated at

2022-04-29 01:18:59 UTC

NP-MRD ID

NP0080268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Khayanoside

Description

Methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0¹,³]Undecane-11-carboxylate belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Khayanoside is found in Khaya ivorensis and Khaya senegalensis . Based on a literature review very few articles have been published on methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0¹,³]Undecane-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203192D          

 46 51  0  0  1  0            999 V2000
   -0.7042    1.2349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3169    1.9634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7541    2.6630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5785    2.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9659    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    1.2061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9160    0.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788   -0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -0.9504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -1.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874   -2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    3.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667    3.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076    1.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    0.5353    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
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  1  0  0  0
 18 19  1  0  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
 18 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 20 29  1  1  0  0  0
 24 30  1  6  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
 21 35  1  6  0  0  0
 19 36  1  6  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 19 40  1  1  0  0  0
 10 41  1  6  0  0  0
  4 42  1  6  0  0  0
 42 43  1  0  0  0  0
  3 44  1  1  0  0  0
  2 45  1  6  0  0  0
  1 46  1  1  0  0  0
M  END

     RDKit          3D

 90 95  0  0  0  0  0  0  0  0999 V2000
   -1.9668    2.2334    3.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128    1.2704    2.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5736    0.1217    2.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840   -0.0214    3.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -0.9204    1.7683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8124   -2.1957    2.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900   -0.8504    1.0481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1085   -1.8279    1.2625 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2721   -1.7257    2.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5110   -3.2498    1.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217   -3.8867   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0508   -3.2451   -2.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7210   -0.2160    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -0.1327   -0.0782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763    1.1497   -0.0076 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    1.6563   -1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    2.0654   -1.8319 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3755    0.9163   -2.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531    1.3710   -3.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    2.8872   -0.9273 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8090    4.0793   -0.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    2.0993    0.2923 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0387    1.4365    0.1124 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5720    1.1899    2.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5293   -0.5571   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333    0.7615   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7292    0.4143   -0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4034    1.6403    0.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    0.0797   -1.2880 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.7709    1.2733   -3.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0649    3.0139   -3.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8376   -0.2825   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0633   -0.7327    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2161   -0.6333    0.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0277   -2.0300    0.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7115   -0.7739    0.8889 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.6167    1.8154    4.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0635    2.4490    4.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -2.9982    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7190    0.1566    1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -0.9778    3.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683   -2.6924    3.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9745   -3.8673    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -4.9251   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344   -4.0134   -1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2844   -1.8059   -2.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193   -0.3514   -1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8973   -2.1750    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -0.0097    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130    0.5923    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7740    1.7618    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3410    2.7434   -2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244    0.5470   -3.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5602    0.0832   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3204    0.8556   -2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9901    2.8403    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4169    1.1655    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6694   -0.2772   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590    1.1304   -1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1735    2.5303   -0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185    1.9649    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134    1.5936    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638   -0.7699   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    0.5481   -3.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1224    2.5837   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3018   -2.0370    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  0
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  5  7  1  0
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  7  8  1  0
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 23 71  1  0
 24 72  1  0
 25 73  1  6
 26 74  1  0
 27 75  1  1
 28 76  1  0
 29 77  1  1
 30 78  1  0
M  END


  Mrv1652304292203192D          

 46 51  0  0  1  0            999 V2000
   -0.7042    1.2349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3169    1.9634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7541    2.6630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5785    2.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9659    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    1.2061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9160    0.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788   -0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -0.9504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -1.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874   -2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    3.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667    3.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076    1.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    0.5353    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
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  1  0  0  0
 18 19  1  0  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
 18 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 20 29  1  1  0  0  0
 24 30  1  6  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
 21 35  1  6  0  0  0
 19 36  1  6  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 19 40  1  1  0  0  0
 10 41  1  6  0  0  0
  4 42  1  6  0  0  0
 42 43  1  0  0  0  0
  3 44  1  1  0  0  0
  2 45  1  6  0  0  0
  1 46  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0080268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@H]1CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O13/c1-29(2)19(15-43-27-23(38)22(37)21(36)17(13-34)44-27)30(3,10-8-20(29)35)18-7-11-31(4)24(16-9-12-42-14-16)45-26(39)25-33(31,46-25)32(18,5)28(40)41-6/h8-10,12,14,17-19,21-25,27,34,36-38H,7,11,13,15H2,1-6H3/t17-,18-,19-,21-,22+,23-,24+,25-,27-,30-,31+,32+,33-/m1/s1

> <INCHI_KEY>
OOWUHRQISTYBRO-MNNHVVHVSA-N

> <FORMULA>
C33H44O13

> <MOLECULAR_WEIGHT>
648.702

> <EXACT_MASS>
648.278191477

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
65.12708884385802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.7614219949999996

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.20025091935132

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210972579115408

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8457181648341545

> <JCHEM_POLAR_SURFACE_AREA>
194.71999999999997

> <JCHEM_REFRACTIVITY>
156.87950000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <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      -1.314   2.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.591   3.665   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.408   4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.947   4.917   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.670   3.557   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.854   2.251   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.577   0.892   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.760  -0.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.483  -1.774   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.929  -4.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.745  -3.187   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.285  -3.241   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.022  -1.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.356  -1.058   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.130  -0.292   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.421   2.445   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.897   3.910   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.437   3.910   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.913   2.445   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.262  -4.493   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.093  -5.746   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.630  -7.105   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.283  -3.755   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -3.763   6.223   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -3.040   7.583   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.685   6.331   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.948   3.719   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -0.498   0.999   0.000  0.00  0.00           O+0
CONECT    1    2    6   46                                                  
CONECT    2    1    3   45                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    5   42                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   18   41                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10   19   23                                                  
CONECT   19   18   20   36   40                                             
CONECT   20   19   21   28   29                                             
CONECT   21   20   22   24   35                                             
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29                                                  
CONECT   29   28   20                                                       
CONECT   30   24   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
CONECT   35   21                                                            
CONECT   36   19   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   19                                                            
CONECT   41   10                                                            
CONECT   42    4   43                                                       
CONECT   43   42                                                            
CONECT   44    3                                                            
CONECT   45    2                                                            
CONECT   46    1                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0,]undecane-11-carboxylic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₃

Average Mass

648.7020 Da

Monoisotopic Mass

648.27819 Da

IUPAC Name

methyl (1R,3S,6R,7S,10R,11R)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-10-[(1R,6S)-1,5,5-trimethyl-4-oxo-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-yl]-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@H]1CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C33H44O13/c1-29(2)19(15-43-27-23(38)22(37)21(36)17(13-34)44-27)30(3,10-8-20(29)35)18-7-11-31(4)24(16-9-12-42-14-16)45-26(39)25-33(31,46-25)32(18,5)28(40)41-6/h8-10,12,14,17-19,21-25,27,34,36-38H,7,11,13,15H2,1-6H3/t17-,18-,19-,21-,22+,23-,24+,25-,27-,30-,31+,32+,33-/m1/s1

InChI Key

OOWUHRQISTYBRO-MNNHVVHVSA-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
Khaya ivorensis	Plant	KNApSAcK
Khaya senegalensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Cyclohexenone
Delta_valerolactone
Dioxepane
Delta valerolactone
1,4-dioxepane
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Heteroaromatic compound
Methyl ester
Furan
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.82	ALOGPS
logP	1.76	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	194.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.88 m³·mol⁻¹	ChemAxon
Polarizability	65.13 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

163032481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Khayanoside (NP0080268)

MOL for NP0080268 (Khayanoside)

3D MOL for NP0080268 (Khayanoside)

3D SDF for NP0080268 (Khayanoside)

3D-SDF for NP0080268 (Khayanoside)

PDB for NP0080268 (Khayanoside)

3D PDB for NP0080268 (Khayanoside)

SMILES for NP0080268 (Khayanoside)

INCHI for NP0080268 (Khayanoside)

Structure for NP0080268 (Khayanoside)

3D Structure for NP0080268 (Khayanoside)