NP-MRD: Showing NP-Card for 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate (NP0279260)

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Record Information

Version

1.0

Created at

2022-09-09 04:35:11 UTC

Updated at

2022-09-09 04:35:11 UTC

NP-MRD ID

NP0279260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate

Description

14-(2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-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. 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate is found in Gratiola officinalis. 14-(2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500332D          

 51 55  0  0  0  0            999 V2000
   -4.4272   -3.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -3.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -3.7981    0.0000 O   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
   -2.7301   -2.1739    0.0000 C   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
    0.5086   -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
   -2.5008   -1.3814    0.0000 C   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
   -2.3558   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 O   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
   -4.3307   -0.1916    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
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    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
   -5.5415   -0.4703    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  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  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 13 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  2  0  0  0  0
 46 44  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
M  END

     RDKit          3D

105109  0  0  0  0  0  0  0  0999 V2000
   -5.9968   -4.5572    2.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8720   -4.3289    1.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2607   -3.0655    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0020   -1.9589    0.2835 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1271   -2.9642    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464   -0.6692    0.7038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2883    0.3630    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    1.4428    1.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155    1.8056    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448    1.2204    0.0880 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6062    0.9468    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826    1.4185    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    1.1218    1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4089    0.4483    0.5627 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4973    1.0568   -0.6658 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841    0.1963   -1.6203 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8624    0.9306   -2.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548    1.5263   -1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7586   -0.9638   -1.0822 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6841   -1.3552   -2.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5525   -0.6437    0.1555 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8306   -0.1892   -0.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8345    0.2854    1.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7965   -0.1858    2.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712    2.2656    2.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2073    2.4061    3.4964 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7074    3.4172    3.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8851    1.4944   -1.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4248   -1.7238   -1.2847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6865   -1.7701   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952   -2.6719   -2.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.3792   -1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586   -0.2904   -3.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7684    2.0208   -1.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    3.3120   -1.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8830   -5.5924    2.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6251    2.1506   -1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.8580   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3920    0.8379   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9595    2.0388   -2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6246    2.7726    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
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 49 99  1  0
 49100  1  0
 49101  1  0
 50102  1  0
 50103  1  0
 50104  1  0
 51105  1  0
M  END


  Mrv1533004201500332D          

 51 55  0  0  0  0            999 V2000
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    5.3238    0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    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
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   -2.0361   -0.6122    0.0000 C   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
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2026    0.6855    0.0000 O   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
   -4.8371    0.4598    0.0000 C   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
   -6.4716    0.2340    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
   -5.5415   -0.4703    0.0000 O   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
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 13 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  2  0  0  0  0
 46 44  1  4  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC2(C)C1C(C)(O)C(=O)C=CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C38H54O13/c1-18(40)49-22-15-35(6)24-11-10-19-20(14-21(31(46)34(19,4)5)50-32-29(45)28(44)27(43)23(17-39)51-32)37(24,8)26(42)16-36(35,7)30(22)38(9,48)25(41)12-13-33(2,3)47/h10,12-14,20,22-24,27-30,32,39,43-45,47-48H,11,15-17H2,1-9H3

> <INCHI_KEY>
WVVGJLXJXQDKGS-UHFFFAOYSA-N

> <FORMULA>
C38H54O13

> <MOLECULAR_WEIGHT>
718.837

> <EXACT_MASS>
718.356441799

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
76.2894295768837

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetate

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.1821819683333317

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.82217075948946

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.127895048354944

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8062198987052955

> <JCHEM_POLAR_SURFACE_AREA>
217.35

> <JCHEM_REFRACTIVITY>
185.02510000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -8.264  -6.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.816  -6.097   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.638  -7.090   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.436  -1.529   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.960  -2.978   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.475  -3.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.999  -4.697   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.515  -4.968   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.468  -2.071   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.984  -2.342   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.945  -0.623   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.938   0.554   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.429  -0.352   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.906   1.096   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.398  -0.418   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -6.829  -2.308   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -12.080   0.437   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -10.765   2.173   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -10.344  -0.878   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   38                                             
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   12   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   13    9   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37    7   39   40                                             
CONECT   39   38                                                            
CONECT   40   38    5   41                                                  
CONECT   41   40   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

View in JSmol

Synonyms

Value	Source
14-(2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetic acid	Generator
14-(2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetic acid	Generator

Chemical Formula

C₃₈H₅₄O₁₃

Average Mass

718.8370 Da

Monoisotopic Mass

718.35644 Da

IUPAC Name

14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-13-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC2(C)C1C(C)(O)C(=O)C=CC(C)(C)O

InChI Identifier

InChI=1S/C38H54O13/c1-18(40)49-22-15-35(6)24-11-10-19-20(14-21(31(46)34(19,4)5)50-32-29(45)28(44)27(43)23(17-39)51-32)37(24,8)26(42)16-36(35,7)30(22)38(9,48)25(41)12-13-33(2,3)47/h10,12-14,20,22-24,27-30,32,39,43-45,47-48H,11,15-17H2,1-9H3

InChI Key

WVVGJLXJXQDKGS-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
Gratiola officinalis	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
25-hydroxysteroid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
Steroid ester
3-oxosteroid
3-oxo-delta-1-steroid
Hydroxysteroid
Oxosteroid
11-oxosteroid
Delta-1-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Acyloin
Monosaccharide
Oxane
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Alpha-hydroxy ketone
Tertiary alcohol
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Polyol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	2.44	ALOGPS
logP	1.18	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	217.35 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	185.03 m³·mol⁻¹	ChemAxon
Polarizability	76.29 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

73802404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate (NP0279260)

MOL for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

3D MOL for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

3D SDF for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

3D-SDF for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

PDB for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

3D PDB for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

SMILES for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

INCHI for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

Structure for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)

3D Structure for NP0279260 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-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-2-yl acetate)