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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:32:18 UTC

Update Date

2021-09-23 06:32:18 UTC

HMDB ID

HMDB0302096

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Kuguacin A

Description

Kuguacin A belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Kuguacin A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241212232D          

 37 40  0  0  0  0            999 V2000
   -3.2411   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.3259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2411   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.5009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8121   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.5009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8121   -0.0884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8121    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    0.7366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3832   -0.0884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4014    0.9915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4014   -0.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863    0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6700   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -2.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -0.9134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    0.3241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516    0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    1.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293   -0.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    1.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634    1.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1044    2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264    0.9915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    0.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1814    1.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  7  2  0  0  0  0
  6  5  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 16  1  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
  3 18  1  1  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  6 21  1  6  0  0  0
  8 22  2  0  0  0  0
  9 23  1  1  0  0  0
 10 24  1  1  0  0  0
 24 25  2  0  0  0  0
 13 26  1  1  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 15 31  1  6  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  END

HMDB0302096
     RDKit          3D
Kuguacin A
 80 83  0  0  0  0  0  0  0  0999 V2000
    3.6346   -1.1634   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.1229    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504    1.1989   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829    1.0712    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012    0.7879   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6225    0.6585    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6827    0.6332   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7867   -0.6049    1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8964    1.7330    1.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    0.2997   -0.2375 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4588    0.1495   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -0.7809   -1.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681   -0.3951   -0.7544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0525    0.9955   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2996   -0.4564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5989   -1.3331   -1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -2.1520   -2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -0.4193   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2036    0.1071   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748   -0.1734    0.7104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8389   -0.7758    1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611    0.3068    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    0.7657    0.3403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3485   -0.1898   -0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    1.0548   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9151    2.4844   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208    0.8803   -2.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4136   -0.9610    0.8311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9212   -2.3032    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249   -3.1871    0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.3894    1.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324    0.1731    1.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4976    0.3667 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7808   -1.9176    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -1.9167   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -1.6136    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6157   -1.0251   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.4225    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    0.9856   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.2090   -0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267    1.2203    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.6500   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2814   -0.0441   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8437    1.6485   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6183    0.1413   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8865   -0.7726    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.5592    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4248   -1.4799    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5007    1.4448    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    1.3866    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -0.2964   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133    1.1211   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5518   -1.8268   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.4669   -2.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    1.7480   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009    0.9809   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662    1.4226   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -2.3369   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.1650   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    0.8155    1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -1.0153    2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2027   -1.6625    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4176    1.1240    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7028   -0.0992    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987    1.6975    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113   -1.0835    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9523    2.6154   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6947    3.0507   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8814    2.9654   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385    1.3233   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    1.4369   -2.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1700   -0.1924   -2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043   -2.4484    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546   -1.1481    2.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6859   -2.0627    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
 28 29  1  1
 29 30  2  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 33 10  1  0
 33 13  1  0
 28 15  1  0
 25 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  6
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 14 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  1
 18 59  1  0
 20 60  1  1
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END


  Mrv0541 02241212232D          

 37 40  0  0  0  0            999 V2000
   -3.2411   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.3259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2411   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.5009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.8121    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4014   -0.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6700   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3832   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    0.3241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516    0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    1.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293   -0.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    1.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634    1.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1044    2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264    0.9915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    0.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1814    1.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  7  2  0  0  0  0
  6  5  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 16  1  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
  3 18  1  1  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  6 21  1  6  0  0  0
  8 22  2  0  0  0  0
  9 23  1  1  0  0  0
 10 24  1  1  0  0  0
 24 25  2  0  0  0  0
 13 26  1  1  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 15 31  1  6  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302096

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C[C@@]12CC[C@]3(C)[C@]([H])(CC[C@@]3(C)[C@]1([H])C(=O)C=C1[C@@]2([H])CC[C@H](O)C1(C)C)C(C)C\C=C\C(O)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-19(9-8-13-26(2,3)34)20-12-14-29(7)25-23(32)17-22-21(10-11-24(33)27(22,4)5)30(25,18-31)16-15-28(20,29)6/h8,13,17-21,24-25,33-34H,9-12,14-16H2,1-7H3/b13-8+/t19?,20-,21-,24+,25+,28-,29+,30-/m1/s1

> <INCHI_KEY>
HJGYRKQQQWEVSH-YPCDWISISA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.257437640859294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,10S,11S,14R,15R)-5-hydroxy-14-[(4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
4.948351895

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.781315978829436

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.237294925268994

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7685201483478828

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
138.1958

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10S,11S,14R,15R)-5-hydroxy-14-[(4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302096
     RDKit          3D
Kuguacin A
 80 83  0  0  0  0  0  0  0  0999 V2000
    3.6346   -1.1634   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.1229    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504    1.1989   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829    1.0712    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012    0.7879   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6225    0.6585    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6827    0.6332   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7867   -0.6049    1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8964    1.7330    1.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    0.2997   -0.2375 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4588    0.1495   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -0.7809   -1.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681   -0.3951   -0.7544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0525    0.9955   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2996   -0.4564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5989   -1.3331   -1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -2.1520   -2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -0.4193   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2036    0.1071   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748   -0.1734    0.7104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8389   -0.7758    1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611    0.3068    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    0.7657    0.3403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3485   -0.1898   -0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    1.0548   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9151    2.4844   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208    0.8803   -2.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4136   -0.9610    0.8311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9212   -2.3032    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249   -3.1871    0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.3894    1.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324    0.1731    1.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4976    0.3667 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7808   -1.9176    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -1.9167   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -1.6136    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6157   -1.0251   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.4225    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    0.9856   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.2090   -0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267    1.2203    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.6500   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2814   -0.0441   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8437    1.6485   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6183    0.1413   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8865   -0.7726    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.5592    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4248   -1.4799    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5007    1.4448    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    1.3866    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -0.2964   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133    1.1211   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5518   -1.8268   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.4669   -2.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    1.7480   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009    0.9809   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662    1.4226   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -2.3369   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.1650   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    0.8155    1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -1.0153    2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2027   -1.6625    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4176    1.1240    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7028   -0.0992    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987    1.6975    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113   -1.0835    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9523    2.6154   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6947    3.0507   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8814    2.9654   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385    1.3233   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    1.4369   -2.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1700   -0.1924   -2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043   -2.4484    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546   -1.1481    2.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141    0.4168    2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5035    0.1035    2.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    1.2562    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -2.2376    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605   -2.6123   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -2.0627    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
 28 29  1  1
 29 30  2  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 33 10  1  0
 33 13  1  0
 28 15  1  0
 25 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  6
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 14 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  1
 18 59  1  0
 20 60  1  1
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.050  -0.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.384  -0.935   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.384  -2.475   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.050  -3.245   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.716  -2.475   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.716  -0.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.383  -3.245   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.049  -2.475   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.049  -0.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.383  -0.165   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.383   1.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.049   2.145   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.715   1.375   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.715  -0.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.749   1.851   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.749  -0.641   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.654   0.605   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.717  -3.245   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.050  -4.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.139  -4.334   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -6.050  -1.705   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0      -0.715  -3.245   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -2.049   0.605   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -4.716   0.605   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.256   0.605   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.317   2.863   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.055  -1.499   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.225   3.315   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.732   3.636   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.195   4.460   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       2.289   1.851   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       3.762   2.491   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.268   2.811   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.299   1.667   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.823   0.202   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.805   1.987   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.329   0.522   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   19   20                                             
CONECT    5    4    7    6                                                  
CONECT    6    1    5   10   21                                             
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   14   10   23                                             
CONECT   10    6    9   11   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   26                                             
CONECT   14    9   16   13   27                                             
CONECT   15   13   17   28   31                                             
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    6                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   10   25                                                       
CONECT   25   24                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   15   29   30                                                  
CONECT   29   28   32                                                       
CONECT   30   28                                                            
CONECT   31   15                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0302096
HETATM    1  C1  UNL     1       3.635  -1.163  -0.048  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.964   0.123   0.238  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.850   1.199  -0.427  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.183   1.071   0.226  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.301   0.788  -0.433  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.622   0.658   0.196  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.683   0.633  -0.891  1.00  0.00           C  
HETATM    8  C8  UNL     1       7.787  -0.605   1.003  1.00  0.00           C  
HETATM    9  O1  UNL     1       7.896   1.733   1.067  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.571   0.300  -0.237  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.459   0.149  -1.760  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.247  -0.781  -1.938  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.568  -0.395  -0.754  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.052   0.996  -0.939  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.720  -1.300  -0.456  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.599  -1.333  -1.641  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.346  -2.152  -2.565  1.00  0.00           O  
HETATM   18  C16 UNL     1      -3.719  -0.419  -1.692  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.204   0.107  -0.600  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.675  -0.173   0.710  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.839  -0.776   1.524  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.861   0.307   1.666  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.417   0.766   0.340  1.00  0.00           C  
HETATM   24  O3  UNL     1      -7.348  -0.190  -0.089  1.00  0.00           O  
HETATM   25  C22 UNL     1      -5.367   1.055  -0.680  1.00  0.00           C  
HETATM   26  C23 UNL     1      -4.915   2.484  -0.599  1.00  0.00           C  
HETATM   27  C24 UNL     1      -6.021   0.880  -2.057  1.00  0.00           C  
HETATM   28  C25 UNL     1      -2.414  -0.961   0.831  1.00  0.00           C  
HETATM   29  C26 UNL     1      -2.921  -2.303   1.349  1.00  0.00           C  
HETATM   30  O4  UNL     1      -3.225  -3.187   0.596  1.00  0.00           O  
HETATM   31  C27 UNL     1      -1.537  -0.389   1.882  1.00  0.00           C  
HETATM   32  C28 UNL     1      -0.232   0.173   1.521  1.00  0.00           C  
HETATM   33  C29 UNL     1       0.488  -0.498   0.367  1.00  0.00           C  
HETATM   34  C30 UNL     1       0.781  -1.918   0.703  1.00  0.00           C  
HETATM   35  H1  UNL     1       3.083  -1.917  -0.603  1.00  0.00           H  
HETATM   36  H2  UNL     1       3.978  -1.614   0.931  1.00  0.00           H  
HETATM   37  H3  UNL     1       4.616  -1.025  -0.598  1.00  0.00           H  
HETATM   38  H4  UNL     1       3.048   0.422   1.331  1.00  0.00           H  
HETATM   39  H5  UNL     1       3.990   0.986  -1.494  1.00  0.00           H  
HETATM   40  H6  UNL     1       3.469   2.209  -0.217  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.227   1.220   1.298  1.00  0.00           H  
HETATM   42  H8  UNL     1       6.176   0.650  -1.521  1.00  0.00           H  
HETATM   43  H9  UNL     1       8.281  -0.044  -1.700  1.00  0.00           H  
HETATM   44  H10 UNL     1       8.844   1.648  -1.286  1.00  0.00           H  
HETATM   45  H11 UNL     1       9.618   0.141  -0.547  1.00  0.00           H  
HETATM   46  H12 UNL     1       8.886  -0.773   1.107  1.00  0.00           H  
HETATM   47  H13 UNL     1       7.342  -0.559   2.000  1.00  0.00           H  
HETATM   48  H14 UNL     1       7.425  -1.480   0.396  1.00  0.00           H  
HETATM   49  H15 UNL     1       8.501   1.445   1.811  1.00  0.00           H  
HETATM   50  H16 UNL     1       1.317   1.387   0.017  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.366  -0.296  -2.189  1.00  0.00           H  
HETATM   52  H18 UNL     1       1.313   1.121  -2.271  1.00  0.00           H  
HETATM   53  H19 UNL     1       0.552  -1.827  -1.993  1.00  0.00           H  
HETATM   54  H20 UNL     1      -0.206  -0.467  -2.909  1.00  0.00           H  
HETATM   55  H21 UNL     1      -0.277   1.748  -1.178  1.00  0.00           H  
HETATM   56  H22 UNL     1      -1.701   0.981  -1.867  1.00  0.00           H  
HETATM   57  H23 UNL     1      -1.666   1.423  -0.151  1.00  0.00           H  
HETATM   58  H24 UNL     1      -1.266  -2.337  -0.395  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.167  -0.165  -2.656  1.00  0.00           H  
HETATM   60  H26 UNL     1      -3.494   0.816   1.245  1.00  0.00           H  
HETATM   61  H27 UNL     1      -4.452  -1.015   2.525  1.00  0.00           H  
HETATM   62  H28 UNL     1      -5.203  -1.663   0.993  1.00  0.00           H  
HETATM   63  H29 UNL     1      -5.418   1.124   2.260  1.00  0.00           H  
HETATM   64  H30 UNL     1      -6.703  -0.099   2.264  1.00  0.00           H  
HETATM   65  H31 UNL     1      -6.999   1.697   0.541  1.00  0.00           H  
HETATM   66  H32 UNL     1      -7.011  -1.084   0.233  1.00  0.00           H  
HETATM   67  H33 UNL     1      -3.952   2.615  -0.064  1.00  0.00           H  
HETATM   68  H34 UNL     1      -5.695   3.051  -0.023  1.00  0.00           H  
HETATM   69  H35 UNL     1      -4.881   2.965  -1.598  1.00  0.00           H  
HETATM   70  H36 UNL     1      -7.038   1.323  -1.949  1.00  0.00           H  
HETATM   71  H37 UNL     1      -5.497   1.437  -2.836  1.00  0.00           H  
HETATM   72  H38 UNL     1      -6.170  -0.192  -2.269  1.00  0.00           H  
HETATM   73  H39 UNL     1      -3.004  -2.448   2.410  1.00  0.00           H  
HETATM   74  H40 UNL     1      -1.355  -1.148   2.696  1.00  0.00           H  
HETATM   75  H41 UNL     1      -2.114   0.417   2.428  1.00  0.00           H  
HETATM   76  H42 UNL     1       0.503   0.104   2.380  1.00  0.00           H  
HETATM   77  H43 UNL     1      -0.261   1.256   1.291  1.00  0.00           H  
HETATM   78  H44 UNL     1      -0.038  -2.238   1.423  1.00  0.00           H  
HETATM   79  H45 UNL     1       0.861  -2.612  -0.139  1.00  0.00           H  
HETATM   80  H46 UNL     1       1.686  -2.063   1.321  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   10   38
CONECT    3    4   39   40
CONECT    4    5    5   41
CONECT    5    6   42
CONECT    6    7    8    9
CONECT    7   43   44   45
CONECT    8   46   47   48
CONECT    9   49
CONECT   10   11   33   50
CONECT   11   12   51   52
CONECT   12   13   53   54
CONECT   13   14   15   33
CONECT   14   55   56   57
CONECT   15   16   28   58
CONECT   16   17   17   18
CONECT   18   19   19   59
CONECT   19   20   25
CONECT   20   21   28   60
CONECT   21   22   61   62
CONECT   22   23   63   64
CONECT   23   24   25   65
CONECT   24   66
CONECT   25   26   27
CONECT   26   67   68   69
CONECT   27   70   71   72
CONECT   28   29   31
CONECT   29   30   30   73
CONECT   31   32   74   75
CONECT   32   33   76   77
CONECT   33   34
CONECT   34   78   79   80
END

HMDB0302096
     RDKit          3D
Kuguacin A
 80 83  0  0  0  0  0  0  0  0999 V2000
    3.6346   -1.1634   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.1229    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504    1.1989   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829    1.0712    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012    0.7879   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6225    0.6585    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6827    0.6332   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7867   -0.6049    1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8964    1.7330    1.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    0.2997   -0.2375 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4588    0.1495   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -0.7809   -1.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681   -0.3951   -0.7544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0525    0.9955   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2996   -0.4564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5989   -1.3331   -1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -2.1520   -2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -0.4193   -1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2036    0.1071   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748   -0.1734    0.7104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8389   -0.7758    1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611    0.3068    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    0.7657    0.3403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3485   -0.1898   -0.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3665    1.0548   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9151    2.4844   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208    0.8803   -2.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4136   -0.9610    0.8311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9212   -2.3032    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249   -3.1871    0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.3894    1.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324    0.1731    1.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.4976    0.3667 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7808   -1.9176    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -1.9167   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -1.6136    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6157   -1.0251   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.4225    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    0.9856   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.2090   -0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267    1.2203    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.6500   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2814   -0.0441   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8437    1.6485   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6183    0.1413   -0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8865   -0.7726    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.5592    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4248   -1.4799    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5007    1.4448    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    1.3866    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -0.2964   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133    1.1211   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5518   -1.8268   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.4669   -2.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    1.7480   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009    0.9809   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662    1.4226   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -2.3369   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.1650   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    0.8155    1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515   -1.0153    2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2027   -1.6625    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4176    1.1240    2.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7028   -0.0992    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987    1.6975    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113   -1.0835    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9523    2.6154   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6947    3.0507   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8814    2.9654   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385    1.3233   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    1.4369   -2.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1700   -0.1924   -2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043   -2.4484    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546   -1.1481    2.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141    0.4168    2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5035    0.1035    2.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    1.2562    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -2.2376    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605   -2.6123   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -2.0627    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
 28 29  1  1
 29 30  2  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 33 10  1  0
 33 13  1  0
 28 15  1  0
 25 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  6
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 14 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  1
 18 59  1  0
 20 60  1  1
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 34 78  1  0
 34 79  1  0
 34 80  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Molecular Weight

470.6838

Monoisotopic Molecular Weight

470.33960996

IUPAC Name

(1R,2R,5S,10S,11S,14R,15R)-5-hydroxy-14-[(4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

Traditional Name

(1R,2R,5S,10S,11S,14R,15R)-5-hydroxy-14-[(4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

O=C[C@@]12CC[C@]3(C)[C@]([H])(CC[C@@]3(C)[C@]1([H])C(=O)C=C1[C@@]2([H])CC[C@H](O)C1(C)C)C(C)C\C=C\C(O)(C)C

InChI Identifier

InChI=1S/C30H46O4/c1-19(9-8-13-26(2,3)34)20-12-14-29(7)25-23(32)17-22-21(10-11-24(33)27(22,4)5)30(25,18-31)16-15-28(20,29)6/h8,13,17-21,24-25,33-34H,9-12,14-16H2,1-7H3/b13-8+/t19?,20-,21-,24+,25+,28-,29+,30-/m1/s1

InChI Key

HJGYRKQQQWEVSH-YPCDWISISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
25-hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
7-oxosteroid
14-alpha-methylsteroid
Delta-5-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Ketone
Secondary alcohol
Aldehyde
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Bitter gourd (FooDB: FOOD00115)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.4	ALOGPS
logP	4.95	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.24	ChemAxon
pKa (Strongest Basic)	-0.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	138.2 m³·mol⁻¹	ChemAxon
Polarizability	55.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	216.187	32859911
AllCCS	[M+H-H2O]+	214.481	32859911
AllCCS	[M+Na]+	218.197	32859911
AllCCS	[M+NH4]+	217.751	32859911
AllCCS	[M-H]-	215.799	32859911
AllCCS	[M+Na-2H]-	218.3	32859911
AllCCS	[M+HCOO]-	221.2	32859911
DeepCCS	[M-2H]-	253.461	30932474
DeepCCS	[M+Na]+	227.232	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kuguacin A,3TMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	3534.5	Semi standard non polar	33892256
Kuguacin A,3TMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	3603.8	Standard non polar	33892256
Kuguacin A,3TMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	3678.1	Standard polar	33892256
Kuguacin A,3TBDMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C(C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	4192.5	Semi standard non polar	33892256
Kuguacin A,3TBDMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C(C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	4261.5	Standard non polar	33892256
Kuguacin A,3TBDMS,isomer #1	CC(C/C=C/C(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H](CC[C@H](O[Si](C)(C)C(C)(C)C)C4(C)C)[C@]3(C=O)CC[C@]12C	3870.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 10V, Positive-QTOF	splash10-0udr-0001900000-31f775d7a98703c7b4f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 20V, Positive-QTOF	splash10-0f79-1105900000-7eb88224423c577b8798	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 40V, Positive-QTOF	splash10-0fwl-1149300000-e012bf6713a6ada22a48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 10V, Negative-QTOF	splash10-014i-0000900000-b14c08dd088e00a23063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 20V, Negative-QTOF	splash10-0uxr-0000900000-c64b20488b911ce1fa27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 40V, Negative-QTOF	splash10-0udr-1002900000-0c37ec8efe19bdd684f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 10V, Positive-QTOF	splash10-0ab9-2905700000-9ceb10a6e0935a9e0016	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 20V, Positive-QTOF	splash10-07vi-9501100000-5f9fdc30cdfa4130d794	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 40V, Positive-QTOF	splash10-06di-9747000000-6810faef205e0f54fcac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 10V, Negative-QTOF	splash10-014i-0000900000-d60788820b8857f5a5d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 20V, Negative-QTOF	splash10-014i-0000900000-dfc26188b60f610287c5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kuguacin A 40V, Negative-QTOF	splash10-00mo-1110900000-1a602577804e54adcc5e	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001852

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Kuguacin A (HMDB0302096)

MOL for HMDB0302096 (Kuguacin A)

3D MOL for HMDB0302096 (Kuguacin A)

3D SDF for HMDB0302096 (Kuguacin A)

3D-SDF for HMDB0302096 (Kuguacin A)

PDB for HMDB0302096 (Kuguacin A)

3D PDB for HMDB0302096 (Kuguacin A)

SMILES for HMDB0302096 (Kuguacin A)

INCHI for HMDB0302096 (Kuguacin A)

Structure for HMDB0302096 (Kuguacin A)

3D Structure for HMDB0302096 (Kuguacin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra