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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:47:31 UTC

Update Date

2022-03-07 02:56:11 UTC

HMDB ID

HMDB0039364

Secondary Accession Numbers

HMDB39364

Metabolite Identification

Common Name

Isolimonic acid 16->17-lactone

Description

Isolimonic acid 16->17-lactone belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Isolimonic acid 16->17-lactone 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 05061311032D          

 35 40  0  0  0  0            999 V2000
    6.3419    1.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702    2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082   -0.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734    2.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8016   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -0.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0762    0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8961   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052    1.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    2.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4844   -0.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    0.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    1.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5298    1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    2.6710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268   -0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -1.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1783   -1.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931    2.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -1.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7591    0.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491    1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23  7  1  0  0  0  0
 23 19  1  0  0  0  0
 24  4  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 12  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 17  1  0  0  0  0
 26 20  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 16  2  0  0  0  0
 28 17  1  0  0  0  0
 29 18  2  0  0  0  0
 30 18  1  0  0  0  0
 31 21  2  0  0  0  0
 32  8  1  0  0  0  0
 32 11  1  0  0  0  0
 33 12  1  0  0  0  0
 33 22  1  0  0  0  0
 34 19  1  0  0  0  0
 34 21  1  0  0  0  0
 35 20  1  0  0  0  0
 35 26  1  0  0  0  0
M  END

HMDB0039364
     RDKit          3D
Isolimonic acid 16->17-lactone
 67 72  0  0  0  0  0  0  0  0999 V2000
   -4.6811   -0.8021    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5644   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401   -1.1729   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    0.7880   -0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280    1.0202   -1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.1796   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750    0.7393    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    0.0011    2.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    2.1506    1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    2.6524    2.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    3.7916    3.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077    1.8653    3.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -1.0602   -0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -2.2593    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -2.1823    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -2.7150    1.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452   -1.4676   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -2.0063   -2.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129   -0.0223   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844    0.8727   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    0.9518   -1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -0.2671   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -0.5885   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781    0.0657    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    1.3940    0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    2.4759    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1675    3.5298    1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885    3.1395    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.8610    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -0.9236    0.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -2.2246    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -3.1457    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -2.5078    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -2.7030   -1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -1.4974   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    0.1291    1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515   -1.4999    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1483   -1.3200    1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -0.6434   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.2194   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7135   -1.1784   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801    2.0639   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    0.5233   -2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9146    0.7218    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.5028    2.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    2.0853    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624    2.8569    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    1.8700    3.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -1.2516   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128   -2.4651    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707   -3.1616   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637   -2.4643   -2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2871   -2.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454   -2.9202   -1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253    0.2595    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067    0.6518   -2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.8866   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    1.8154   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    1.3710   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -1.4555   -2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.2524   -2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.8096   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623   -0.1271    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661    2.5225    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    4.5281    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284    1.3188   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -3.4325    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 24 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 13  2  1  0
 35 17  1  0
 19  6  1  0
 35 22  1  0
 29 25  2  0
 35 33  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 26 64  1  0
 27 65  1  0
 29 66  1  0
 33 67  1  0
M  END


  Mrv0541 05061311032D          

 35 40  0  0  0  0            999 V2000
    6.3419    1.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702    2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082   -0.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734    2.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8016   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -0.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0762    0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8961   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052    1.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    2.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4844   -0.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    0.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    1.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5298    1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    2.6710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268   -0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -1.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1783   -1.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931    2.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -1.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7591    0.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491    1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23  7  1  0  0  0  0
 23 19  1  0  0  0  0
 24  4  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 12  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 17  1  0  0  0  0
 26 20  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 16  2  0  0  0  0
 28 17  1  0  0  0  0
 29 18  2  0  0  0  0
 30 18  1  0  0  0  0
 31 21  2  0  0  0  0
 32  8  1  0  0  0  0
 32 11  1  0  0  0  0
 33 12  1  0  0  0  0
 33 22  1  0  0  0  0
 34 19  1  0  0  0  0
 34 21  1  0  0  0  0
 35 20  1  0  0  0  0
 35 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039364

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OCC2(C(O)CC(O)=O)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15,12-33-22)17(28)10-18(29)30)5-7-23(3)19(13-6-8-32-11-13)34-21(31)20-26(23,24)35-20/h6,8,11,14-15,17,19-20,28H,5,7,9-10,12H2,1-4H3,(H,29,30)

> <INCHI_KEY>
SZSLZBYOLTYIOE-UHFFFAOYSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.5269

> <EXACT_MASS>
488.204632622

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.953968970236346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[7-(furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-12-yl]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.7927200163333317

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.62524540765915

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.06534561653953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0876446351304576

> <JCHEM_POLAR_SURFACE_AREA>
135.79999999999998

> <JCHEM_REFRACTIVITY>
118.21139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[7-(furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-12-yl]-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039364
     RDKit          3D
Isolimonic acid 16->17-lactone
 67 72  0  0  0  0  0  0  0  0999 V2000
   -4.6811   -0.8021    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5644   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401   -1.1729   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    0.7880   -0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280    1.0202   -1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.1796   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750    0.7393    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    0.0011    2.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    2.1506    1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    2.6524    2.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    3.7916    3.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077    1.8653    3.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -1.0602   -0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -2.2593    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -2.1823    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -2.7150    1.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452   -1.4676   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -2.0063   -2.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129   -0.0223   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844    0.8727   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    0.9518   -1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -0.2671   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -0.5885   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781    0.0657    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    1.3940    0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    2.4759    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1675    3.5298    1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885    3.1395    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.8610    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -0.9236    0.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -2.2246    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -3.1457    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -2.5078    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -2.7030   -1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -1.4974   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    0.1291    1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515   -1.4999    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1483   -1.3200    1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -0.6434   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.2194   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7135   -1.1784   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801    2.0639   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    0.5233   -2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9146    0.7218    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.5028    2.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    2.0853    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624    2.8569    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    1.8700    3.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -1.2516   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128   -2.4651    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707   -3.1616   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637   -2.4643   -2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2871   -2.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454   -2.9202   -1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253    0.2595    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067    0.6518   -2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.8866   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    1.8154   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    1.3710   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -1.4555   -2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.2524   -2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.8096   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623   -0.1271    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661    2.5225    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    4.5281    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284    1.3188   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -3.4325    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 24 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 13  2  1  0
 35 17  1  0
 19  6  1  0
 35 22  1  0
 29 25  2  0
 35 33  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 26 64  1  0
 27 65  1  0
 29 66  1  0
 33 67  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.838   3.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.211   4.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.189  -0.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.255   1.201   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.221  -0.266   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.537  -2.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.705  -0.537   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.592  -3.569   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.790   4.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.096  -0.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.193  -1.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.476   0.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.673  -1.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.744   1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.783   2.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.274   3.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.371  -0.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.207  -2.482   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.196   0.370   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.242   3.266   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.726   2.995   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.322   2.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.712   0.641   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.751   2.360   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.260   1.454   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.235   2.089   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.282   4.986   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.757  -0.754   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.593  -3.154   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.933  -3.347   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.734   4.173   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.143  -3.046   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.750   1.373   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.203   1.547   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.758   3.537   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    7   14                                                       
CONECT    6    8   13                                                       
CONECT    7    5   23                                                       
CONECT    8    6   32                                                       
CONECT    9   15   16                                                       
CONECT   10   17   18                                                       
CONECT   11   13   32                                                       
CONECT   12   25   33                                                       
CONECT   13    6   11   19                                                  
CONECT   14    5   24   25                                                  
CONECT   15    9   22   25                                                  
CONECT   16    9   24   27                                                  
CONECT   17   10   25   28                                                  
CONECT   18   10   29   30                                                  
CONECT   19   13   23   34                                                  
CONECT   20   21   26   35                                                  
CONECT   21   20   31   34                                                  
CONECT   22    1    2   15   33                                             
CONECT   23    3    7   19   26                                             
CONECT   24    4   14   16   26                                             
CONECT   25   12   14   15   17                                             
CONECT   26   20   23   24   35                                             
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   18                                                            
CONECT   31   21                                                            
CONECT   32    8   11                                                       
CONECT   33   12   22                                                       
CONECT   34   19   21                                                       
CONECT   35   20   26                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

COMPND    HMDB0039364
HETATM    1  C1  UNL     1      -4.681  -0.802   0.800  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.851  -0.564  -0.409  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.640  -1.173  -1.588  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.740   0.788  -0.767  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.428   1.020  -1.182  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.638   0.180  -0.166  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.875   0.739   1.238  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.175   0.001   2.192  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.291   2.151   1.342  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.543   2.652   2.717  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.175   3.792   3.102  1.00  0.00           O  
HETATM   12  O4  UNL     1      -2.208   1.865   3.645  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.487  -1.060  -0.430  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.046  -2.259   0.290  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.560  -2.182   0.367  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.017  -2.715   1.283  1.00  0.00           O  
HETATM   17  C12 UNL     1       0.245  -1.468  -0.653  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.012  -2.006  -2.046  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.213  -0.022  -0.488  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.384   0.873  -1.506  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.862   0.952  -1.180  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.492  -0.267  -0.666  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.635  -0.589  -1.615  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.178   0.066   0.669  1.00  0.00           C  
HETATM   25  C20 UNL     1       3.774   1.394   0.704  1.00  0.00           C  
HETATM   26  C21 UNL     1       3.316   2.476   1.453  1.00  0.00           C  
HETATM   27  C22 UNL     1       4.167   3.530   1.194  1.00  0.00           C  
HETATM   28  O6  UNL     1       5.088   3.139   0.349  1.00  0.00           O  
HETATM   29  C23 UNL     1       4.880   1.861   0.035  1.00  0.00           C  
HETATM   30  O7  UNL     1       4.197  -0.924   0.795  1.00  0.00           O  
HETATM   31  C24 UNL     1       3.778  -2.225   0.721  1.00  0.00           C  
HETATM   32  O8  UNL     1       4.572  -3.146   1.012  1.00  0.00           O  
HETATM   33  C25 UNL     1       2.381  -2.508   0.294  1.00  0.00           C  
HETATM   34  O9  UNL     1       2.303  -2.703  -1.112  1.00  0.00           O  
HETATM   35  C26 UNL     1       1.708  -1.497  -0.411  1.00  0.00           C  
HETATM   36  H1  UNL     1      -5.204   0.129   1.174  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.551  -1.500   0.600  1.00  0.00           H  
HETATM   38  H3  UNL     1      -4.148  -1.320   1.643  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.410  -0.643  -2.528  1.00  0.00           H  
HETATM   40  H5  UNL     1      -4.307  -2.219  -1.716  1.00  0.00           H  
HETATM   41  H6  UNL     1      -5.714  -1.178  -1.395  1.00  0.00           H  
HETATM   42  H7  UNL     1      -2.180   2.064  -1.169  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.271   0.523  -2.162  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.915   0.722   1.544  1.00  0.00           H  
HETATM   45  H10 UNL     1      -0.545   0.503   2.727  1.00  0.00           H  
HETATM   46  H11 UNL     1      -0.190   2.085   1.231  1.00  0.00           H  
HETATM   47  H12 UNL     1      -1.762   2.857   0.656  1.00  0.00           H  
HETATM   48  H13 UNL     1      -3.221   1.870   3.598  1.00  0.00           H  
HETATM   49  H14 UNL     1      -2.273  -1.252  -1.531  1.00  0.00           H  
HETATM   50  H15 UNL     1      -2.513  -2.465   1.262  1.00  0.00           H  
HETATM   51  H16 UNL     1      -2.271  -3.162  -0.345  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.964  -2.464  -2.472  1.00  0.00           H  
HETATM   53  H18 UNL     1      -0.280  -1.287  -2.800  1.00  0.00           H  
HETATM   54  H19 UNL     1      -0.645  -2.920  -1.980  1.00  0.00           H  
HETATM   55  H20 UNL     1       0.325   0.260   0.483  1.00  0.00           H  
HETATM   56  H21 UNL     1       0.207   0.652  -2.553  1.00  0.00           H  
HETATM   57  H22 UNL     1      -0.101   1.887  -1.351  1.00  0.00           H  
HETATM   58  H23 UNL     1       1.956   1.815  -0.463  1.00  0.00           H  
HETATM   59  H24 UNL     1       2.331   1.371  -2.123  1.00  0.00           H  
HETATM   60  H25 UNL     1       3.379  -1.455  -2.261  1.00  0.00           H  
HETATM   61  H26 UNL     1       3.825   0.252  -2.327  1.00  0.00           H  
HETATM   62  H27 UNL     1       4.554  -0.810  -1.086  1.00  0.00           H  
HETATM   63  H28 UNL     1       2.462  -0.127   1.494  1.00  0.00           H  
HETATM   64  H29 UNL     1       2.466   2.522   2.118  1.00  0.00           H  
HETATM   65  H30 UNL     1       4.079   4.528   1.630  1.00  0.00           H  
HETATM   66  H31 UNL     1       5.528   1.319  -0.659  1.00  0.00           H  
HETATM   67  H32 UNL     1       2.018  -3.433   0.781  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    4   13
CONECT    3   39   40   41
CONECT    4    5
CONECT    5    6   42   43
CONECT    6    7   13   19
CONECT    7    8    9   44
CONECT    8   45
CONECT    9   10   46   47
CONECT   10   11   11   12
CONECT   12   48
CONECT   13   14   49
CONECT   14   15   50   51
CONECT   15   16   16   17
CONECT   17   18   19   35
CONECT   18   52   53   54
CONECT   19   20   55
CONECT   20   21   56   57
CONECT   21   22   58   59
CONECT   22   23   24   35
CONECT   23   60   61   62
CONECT   24   25   30   63
CONECT   25   26   29   29
CONECT   26   27   27   64
CONECT   27   28   65
CONECT   28   29
CONECT   29   66
CONECT   30   31
CONECT   31   32   32   33
CONECT   33   34   35   67
CONECT   34   35
END

HMDB0039364
     RDKit          3D
Isolimonic acid 16->17-lactone
 67 72  0  0  0  0  0  0  0  0999 V2000
   -4.6811   -0.8021    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -0.5644   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401   -1.1729   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    0.7880   -0.7674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280    1.0202   -1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.1796   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750    0.7393    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    0.0011    2.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    2.1506    1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    2.6524    2.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    3.7916    3.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2077    1.8653    3.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868   -1.0602   -0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -2.2593    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -2.1823    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -2.7150    1.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452   -1.4676   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -2.0063   -2.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129   -0.0223   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844    0.8727   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    0.9518   -1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -0.2671   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -0.5885   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781    0.0657    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745    1.3940    0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    2.4759    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1675    3.5298    1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885    3.1395    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.8610    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -0.9236    0.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -2.2246    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -3.1457    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -2.5078    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -2.7030   -1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -1.4974   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    0.1291    1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5515   -1.4999    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1483   -1.3200    1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -0.6434   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.2194   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7135   -1.1784   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801    2.0639   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    0.5233   -2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9146    0.7218    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5452    0.5028    2.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    2.0853    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624    2.8569    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    1.8700    3.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -1.2516   -1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128   -2.4651    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707   -3.1616   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637   -2.4643   -2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796   -1.2871   -2.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454   -2.9202   -1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253    0.2595    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067    0.6518   -2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.8866   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    1.8154   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    1.3710   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -1.4555   -2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.2524   -2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.8096   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623   -0.1271    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661    2.5225    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    4.5281    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284    1.3188   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -3.4325    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 24 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 13  2  1  0
 35 17  1  0
 19  6  1  0
 35 22  1  0
 29 25  2  0
 35 33  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 26 64  1  0
 27 65  1  0
 29 66  1  0
 33 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isolimonate 16->17-lactone	Generator
3-[7-(Furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-12-yl]-3-hydroxypropanoate	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Molecular Weight

488.5269

Monoisotopic Molecular Weight

488.204632622

IUPAC Name

3-[7-(furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-12-yl]-3-hydroxypropanoic acid

Traditional Name

3-[7-(furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-12-yl]-3-hydroxypropanoic acid

CAS Registry Number

74729-97-8

SMILES

CC1(C)OCC2(C(O)CC(O)=O)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

InChI Identifier

InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15,12-33-22)17(28)10-18(29)30)5-7-23(3)19(13-6-8-32-11-13)34-21(31)20-26(23,24)35-20/h6,8,11,14-15,17,19-20,28H,5,7,9-10,12H2,1-4H3,(H,29,30)

InChI Key

SZSLZBYOLTYIOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039364)

Biofluid or Excreta

Urine (HMDB: HMDB0039364)

Tissue substructure

Hepatic tissue (HMDB: HMDB0039364)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039364)

Source

Endogenous

Endogenous (HMDB: HMDB0039364)

Plant

Plant (HMDB: HMDB0039364)

Animal

Animal (HMDB: HMDB0039364)

Exogenous

Food

Food (HMDB: HMDB0039364)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039364)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039364)

Cellular process

Cell signaling (HMDB: HMDB0039364)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039364)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039364)

Nutrient

Nutrient (HMDB: HMDB0039364)

Molecular messenger

Signaling molecule (HMDB: HMDB0039364)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039364)

Emulsifier (HMDB: HMDB0039364)

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
Water Solubility	0.14 g/L	ALOGPS
logP	2.44	ALOGPS
logP	1.79	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.21 m³·mol⁻¹	ChemAxon
Polarizability	48.95 Å³	ChemAxon
Number of Rings	6	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
DarkChem	[M+H]+	209.937	31661259
DarkChem	[M-H]-	199.855	31661259
DeepCCS	[M-2H]-	242.315	30932474
DeepCCS	[M+Na]+	217.74	30932474
AllCCS	[M+H]+	210.8	32859911
AllCCS	[M+H-H2O]+	209.0	32859911
AllCCS	[M+NH4]+	212.5	32859911
AllCCS	[M+Na]+	213.0	32859911
AllCCS	[M-H]-	215.4	32859911
AllCCS	[M+Na-2H]-	216.6	32859911
AllCCS	[M+HCOO]-	218.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isolimonic acid 16->17-lactone	CC1(C)OCC2(C(O)CC(O)=O)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1	4097.7	Standard polar	33892256
Isolimonic acid 16->17-lactone	CC1(C)OCC2(C(O)CC(O)=O)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1	3163.9	Standard non polar	33892256
Isolimonic acid 16->17-lactone	CC1(C)OCC2(C(O)CC(O)=O)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1	4174.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isolimonic acid 16->17-lactone,1TMS,isomer #1	CC1(C)OCC2(C(CC(=O)O)O[Si](C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3638.6	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,1TMS,isomer #2	CC1(C)OCC2(C(O)CC(=O)O[Si](C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3658.2	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,1TMS,isomer #3	CC1(C)OCC2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3620.7	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3562.9	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TMS,isomer #2	CC1(C)OCC2(C(CC(=O)O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3516.0	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TMS,isomer #3	CC1(C)OCC2(C(O)CC(=O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3526.1	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,3TMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3440.6	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,3TMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3429.5	Standard non polar	33892256
Isolimonic acid 16->17-lactone,1TBDMS,isomer #1	CC1(C)OCC2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3882.6	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,1TBDMS,isomer #2	CC1(C)OCC2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3904.2	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,1TBDMS,isomer #3	CC1(C)OCC2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3869.8	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TBDMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	4022.2	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TBDMS,isomer #2	CC1(C)OCC2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3986.5	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,2TBDMS,isomer #3	CC1(C)OCC2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3976.3	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,3TBDMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	4062.8	Semi standard non polar	33892256
Isolimonic acid 16->17-lactone,3TBDMS,isomer #1	CC1(C)OCC2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	4061.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isolimonic acid 16->17-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-002r-4071900000-e9eeb03fd67229f050b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isolimonic acid 16->17-lactone GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-8042169000-e4acf5d83185986e8398	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isolimonic acid 16->17-lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 10V, Positive-QTOF	splash10-0fki-0000900000-551438752c17ceac1c2d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 20V, Positive-QTOF	splash10-0fmi-0000900000-b30ccfec4890955dcc5f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 40V, Positive-QTOF	splash10-0012-9124200000-da4c68f45ea0dd2c8fe0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 10V, Negative-QTOF	splash10-000f-1001900000-703638c495911e9148df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 20V, Negative-QTOF	splash10-0ard-3004900000-683aed9be5f89910440c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 40V, Negative-QTOF	splash10-0aos-9008500000-7b60bc9e86e82f9b83b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 10V, Positive-QTOF	splash10-000i-0000900000-a15341552ef523ca37c3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 20V, Positive-QTOF	splash10-0fe3-0001900000-423ab933a6ad68b77cf7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 40V, Positive-QTOF	splash10-052b-3469800000-e176cd2e251bce8e4194	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 10V, Negative-QTOF	splash10-0006-0001900000-770406018ecd07aa8d2d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 20V, Negative-QTOF	splash10-0002-0009000000-f9378df328e76499ebc1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 16->17-lactone 40V, Negative-QTOF	splash10-006x-9002000000-3a7e7c91aba5a876a238	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB018922

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

25022666

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Isolimonic acid 16->17-lactone (HMDB0039364)

MOL for HMDB0039364 (Isolimonic acid 16->17-lactone)

3D MOL for HMDB0039364 (Isolimonic acid 16->17-lactone)

3D SDF for HMDB0039364 (Isolimonic acid 16->17-lactone)

3D-SDF for HMDB0039364 (Isolimonic acid 16->17-lactone)

PDB for HMDB0039364 (Isolimonic acid 16->17-lactone)

3D PDB for HMDB0039364 (Isolimonic acid 16->17-lactone)

SMILES for HMDB0039364 (Isolimonic acid 16->17-lactone)

INCHI for HMDB0039364 (Isolimonic acid 16->17-lactone)

Structure for HMDB0039364 (Isolimonic acid 16->17-lactone)

3D Structure for HMDB0039364 (Isolimonic acid 16->17-lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra