NP-MRD: Showing NP-Card for 6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate (NP0204750)

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Record Information

Version

2.0

Created at

2022-09-05 00:29:15 UTC

Updated at

2022-09-05 00:29:15 UTC

NP-MRD ID

NP0204750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

Description

6-(9,13-Dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate is found in Citrullus colocynthis. 6-(9,13-Dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522362D          

 52 56  0  0  0  0            999 V2000
   -7.7952    0.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9779    0.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6670    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283   -1.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8207   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328   -2.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -1.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -1.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920   -0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3238    0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798   -0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6995    0.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -3.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -3.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  5  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 28 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 25 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 26 46  1  0  0  0  0
 21 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 15 51  1  0  0  0  0
 19 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END

     RDKit          3D

106110  0  0  0  0  0  0  0  0999 V2000
   -6.6664   -2.2330    3.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7355   -1.0493    2.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1210    0.1956    3.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2085    1.3501    2.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7171    2.4204    3.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3633    1.2394    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9400    1.8296    1.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3206    1.8125    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6017    1.2923   -0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6612    0.6954   -0.9531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    1.4565   -1.8180 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2521    2.9075   -1.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345    1.2274   -2.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5798    0.4729   -1.9560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7320    0.8190   -3.1765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5525    0.8366   -4.3071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.4212   -3.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -0.9231   -1.7724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4950   -2.2601   -1.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -1.2009   -1.2774 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3525   -2.0401   -2.2577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2853   -3.2810   -2.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634   -2.3874   -1.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991   -1.7486   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   -0.6135   -0.0290 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6176    0.4239    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9353    0.2166    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6732   -0.0751    1.9683 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.4912   -2.4662    1.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9059    3.4064    0.8272 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5677   -1.2123   -0.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5385   -2.2295   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -2.5916    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -3.4299   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.0387   -0.8768 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0319    0.7579   -1.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    0.8280   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    1.1945    1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5640    0.1278   -0.9702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0570   -0.5826    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0168   -3.1256    2.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6976    0.2772   -2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -0.4931   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0897    1.6764   -3.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354    0.6091   -5.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -0.1641   -3.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -1.1416   -3.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240   -2.9778   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -2.6873   -2.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -2.2055   -1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162   -1.8410   -0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.5126   -3.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4327    1.2113    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3076   -4.2613   -0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990   -3.2089   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9780   -3.7610   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2978    1.5132   -2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    0.2013   -2.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
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 47100  1  0
 47101  1  0
 50102  1  0
 50103  1  0
 52104  1  0
 52105  1  0
 52106  1  0
M  END


  Mrv1533004171522362D          

 52 56  0  0  0  0            999 V2000
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    3.7283   -1.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8844   -1.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0520   -1.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  5  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 10 12  1  0  0  0  0
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 16 18  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 28 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 25 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 26 46  1  0  0  0  0
 21 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 15 51  1  0  0  0  0
 19 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3C(O)C=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C38H54O14/c1-17(40)52-33(2,3)11-10-24(43)38(9,49)30-21(42)14-35(6)29-20(41)12-18-19(37(29,8)25(44)15-36(30,35)7)13-22(31(48)34(18,4)5)50-32-28(47)27(46)26(45)23(16-39)51-32/h10-13,19-21,23,26-30,32,39,41-42,45-47,49H,14-16H2,1-9H3

> <INCHI_KEY>
VJTYFWONTVLZJR-UHFFFAOYSA-N

> <FORMULA>
C38H54O14

> <MOLECULAR_WEIGHT>
734.836

> <EXACT_MASS>
734.351356419

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
76.53136127199602

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(9,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
0.02932463133333249

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.814831537071807

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.126024694162282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8839254921082933

> <JCHEM_POLAR_SURFACE_AREA>
237.57999999999998

> <JCHEM_REFRACTIVITY>
186.4636000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(9,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0     -14.551   1.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.025   1.653   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -12.445   3.079   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -12.080   0.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.344  -0.878   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.765   2.173   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.829  -2.308   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.398  -0.418   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.559  -6.874   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.436  -1.529   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.960  -2.978   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.475  -3.249   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.999  -4.697   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.515  -4.968   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.468  -2.071   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.984  -2.342   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.945  -0.623   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.938   0.554   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.429  -0.352   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.906   1.096   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   51                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   51                                             
CONECT   20   19                                                            
CONECT   21   19   22   46                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   43                                                  
CONECT   26   25   27   46                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   41                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   39                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   30   40                                                  
CONECT   40   39                                                            
CONECT   41   28   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   25   44   45                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   26   21   47   48                                             
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   15   19   52                                             
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Value	Source
6-(9,13-Dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid	Generator
6-(9,13-Dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid	Generator

Chemical Formula

C₃₈H₅₄O₁₄

Average Mass

734.8360 Da

Monoisotopic Mass

734.35136 Da

IUPAC Name

6-(9,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C)(C)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3C(O)C=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C

InChI Identifier

InChI=1S/C38H54O14/c1-17(40)52-33(2,3)11-10-24(43)38(9,49)30-21(42)14-35(6)29-20(41)12-18-19(37(29,8)25(44)15-36(30,35)7)13-22(31(48)34(18,4)5)50-32-28(47)27(46)26(45)23(16-39)51-32/h10-13,19-21,23,26-30,32,39,41-42,45-47,49H,14-16H2,1-9H3

InChI Key

VJTYFWONTVLZJR-UHFFFAOYSA-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
Citrullus colocynthis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Cucurbitacin skeleton
Triterpenoid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
Steroid ester
3-oxo-delta-1-steroid
3-oxosteroid
Hydroxysteroid
7-hydroxysteroid
16-hydroxysteroid
11-oxosteroid
Oxosteroid
Delta-1-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Oxane
Acyloin
Monosaccharide
Tertiary alcohol
Acryloyl-group
Alpha-hydroxy ketone
Alpha,beta-unsaturated ketone
Enone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.65	ALOGPS
logP	0.029	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	237.58 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	186.46 m³·mol⁻¹	ChemAxon
Polarizability	76.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73034991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate (NP0204750)

MOL for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D MOL for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D SDF for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D-SDF for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

PDB for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D PDB for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

SMILES for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

INCHI for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

Structure for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D Structure for NP0204750 (6-(2,4-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-1-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)