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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:53:02 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038560

Secondary Accession Numbers

HMDB38560

Metabolite Identification

Common Name

8-Butanoylneosolaniol

Description

8-Butanoylneosolaniol, also known as isopropyl butyric acid or 1-methylethyl butanoate, belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Based on a literature review a small amount of articles have been published on 8-Butanoylneosolaniol.

Structure

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

  Mrv0541 01251307522D          

 34 37  0  0  0  0            999 V2000
   -1.0695   -4.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -4.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -5.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0695   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -5.7897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3550   -4.9647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3594   -4.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -6.2022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0739   -5.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0739   -4.9647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4984   -4.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -6.2022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -6.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -7.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -5.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -6.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -7.5320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0848   -6.1236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8855   -5.9247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -8.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6418   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3563   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -4.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -7.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -8.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -7.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -8.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -9.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430   -9.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719   -9.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -4.1397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874   -4.1678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  2  0  0  0  0
 13 28  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 30 20  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  9 15  1  6  0  0  0
  6 33  1  6  0  0  0
 10 34  1  1  0  0  0
M  END

HMDB0038560
     RDKit          3D
8-Butanoylneosolaniol
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.5951    0.2143   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.3034   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344   -0.2718   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -0.1354   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0143    0.3990    1.1070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -0.5664   -0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906   -0.4625    0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4227    0.3202   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.0425   -0.0246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5890   -0.7701   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.9303   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -2.8068   -2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -3.9897   -2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419   -2.5300   -3.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -0.9374    1.1790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1749   -2.0808    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614   -1.8627    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886   -3.0202    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.2959    2.3765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.8788    2.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9911    0.7749    2.3364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5349   -0.3908    2.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500    0.8886    0.8275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9747    1.9862    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336    1.7549   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    2.8926   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930    0.5666   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    1.2238    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8500    2.1062   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    1.8699    1.4602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2206    2.8495    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    3.1722    1.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179   -0.7887   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4288    0.3734   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121    1.0178   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492    1.3690    0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -0.1985    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9878    0.3970   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.3147   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193    0.0250    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6022    0.2054   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6021    1.3895   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -0.9705   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -0.1264   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661   -4.3429   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -3.8094   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -4.8424   -3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1310   -1.3272    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -3.0798    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.6966    0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -3.3301   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155   -3.8521    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.2693    3.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    1.6910    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -0.1420    3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -0.0640    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6990    2.5826   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6055    3.2386    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3629    3.6980   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131    1.8261   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393    2.0337   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.1532   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    3.5216    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    2.9861    2.5665 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  0
 17  7  1  0
 30 20  1  0
 28  9  1  0
 30 32  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  1
 16 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  1
 21 54  1  1
 22 55  1  0
 23 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
M  END

  Mrv0541 01251307522D          

 34 37  0  0  0  0            999 V2000
   -1.0695   -4.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -4.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -5.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0695   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -5.7897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3550   -4.9647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3594   -4.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -6.2022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0739   -5.7897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0739   -4.9647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4984   -4.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -6.2022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -6.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -7.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -5.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -6.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -7.5320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0848   -6.1236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8855   -5.9247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -8.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6418   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3563   -6.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -4.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -7.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840   -8.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -7.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -8.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -9.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430   -9.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719   -9.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -4.1397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874   -4.1678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  2  0  0  0  0
 13 28  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 30 20  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  9 15  1  6  0  0  0
  6 33  1  6  0  0  0
 10 34  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0038560

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O9/c1-6-7-17(26)31-15-9-22(10-28-13(3)24)16(8-12(15)2)32-20-18(27)19(30-14(4)25)21(22,5)23(20)11-29-23/h8,15-16,18-20,27H,6-7,9-11H2,1-5H3/t15-,16+,18+,19+,20+,21+,22+,23-/m0/s1

> <INCHI_KEY>
QAZLVSRKBUTUHB-MXINJKJASA-N

> <FORMULA>
C23H32O9

> <MOLECULAR_WEIGHT>
452.4948

> <EXACT_MASS>
452.204632622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.464419421194265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl butanoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
0.7324184606666655

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.072305054496205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64197376916336

> <JCHEM_POLAR_SURFACE_AREA>
120.89000000000001

> <JCHEM_REFRACTIVITY>
108.99459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038560
     RDKit          3D
8-Butanoylneosolaniol
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.5951    0.2143   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.3034   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344   -0.2718   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -0.1354   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0143    0.3990    1.1070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -0.5664   -0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906   -0.4625    0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4227    0.3202   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.0425   -0.0246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5890   -0.7701   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.9303   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -2.8068   -2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -3.9897   -2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419   -2.5300   -3.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -0.9374    1.1790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1749   -2.0808    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614   -1.8627    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886   -3.0202    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.2959    2.3765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.8788    2.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9911    0.7749    2.3364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5349   -0.3908    2.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500    0.8886    0.8275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9747    1.9862    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336    1.7549   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    2.8926   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930    0.5666   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    1.2238    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8500    2.1062   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    1.8699    1.4602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2206    2.8495    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    3.1722    1.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179   -0.7887   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4288    0.3734   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121    1.0178   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492    1.3690    0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -0.1985    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9878    0.3970   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.3147   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193    0.0250    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6022    0.2054   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6021    1.3895   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -0.9705   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -0.1264   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661   -4.3429   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -3.8094   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -4.8424   -3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1310   -1.3272    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -3.0798    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.6966    0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -3.3301   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155   -3.8521    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.2693    3.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    1.6910    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -0.1420    3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -0.0640    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6990    2.5826   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6055    3.2386    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3629    3.6980   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131    1.8261   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393    2.0337   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.1532   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    3.5216    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    2.9861    2.5665 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  0
 17  7  1  0
 30 20  1  0
 28  9  1  0
 30 32  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  1
 16 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  1
 21 54  1  1
 22 55  1  0
 23 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
M  END

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0      -1.996  -8.497   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.330  -9.267   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.330 -10.807   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.996 -11.577   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.663 -10.807   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.663  -9.267   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.671  -8.497   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.671 -11.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.005 -10.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.005  -9.267   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.664  -8.497   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.664 -11.577   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.663 -12.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.671 -13.117   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.545 -10.807   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.775 -12.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.106 -14.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.758 -11.431   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.253 -11.059   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.400 -15.571   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.997 -10.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.331 -11.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.665 -10.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.998 -11.577   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.997  -9.267   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.996 -14.657   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.330 -15.427   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.996 -13.117   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.663 -15.427   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.400 -17.111   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.067 -17.881   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.734 -17.881   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      -0.663  -7.727   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.403  -7.780   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    1    7    5   33                                             
CONECT    7    6   10                                                       
CONECT    8    5    9   14   17                                             
CONECT    9    8   10   16   15                                             
CONECT   10    9    7   18   34                                             
CONECT   11    2                                                            
CONECT   12    3   21                                                       
CONECT   13    5   28                                                       
CONECT   14    8                                                            
CONECT   15   16    9                                                       
CONECT   16    9   15                                                       
CONECT   17    8   18   20                                                  
CONECT   18   10   17   19                                                  
CONECT   19   18                                                            
CONECT   20   17   30                                                       
CONECT   21   12   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21                                                            
CONECT   26   27   28   29                                                  
CONECT   27   26                                                            
CONECT   28   13   26                                                       
CONECT   29   26                                                            
CONECT   30   20   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    6                                                            
CONECT   34   10                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0038560
HETATM    1  C1  UNL     1       7.595   0.214  -0.835  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.300   0.303  -0.084  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.134  -0.272  -0.841  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.915  -0.135  -0.019  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.014   0.399   1.107  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.680  -0.566  -0.432  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.491  -0.462   0.306  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.423   0.320  -0.387  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.978  -0.043  -0.025  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.589  -0.770  -1.204  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.819  -1.930  -1.460  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.142  -2.807  -2.495  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.294  -3.990  -2.697  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.142  -2.530  -3.193  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.097  -0.937   1.179  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.175  -2.081   1.054  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.061  -1.863   0.638  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.989  -3.020   0.515  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.832  -0.296   2.376  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.498   0.879   2.570  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.991   0.775   2.336  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.535  -0.391   2.840  1.00  0.00           O  
HETATM   23  C17 UNL     1      -3.150   0.889   0.827  1.00  0.00           C  
HETATM   24  O7  UNL     1      -3.975   1.986   0.481  1.00  0.00           O  
HETATM   25  C18 UNL     1      -5.134   1.755  -0.242  1.00  0.00           C  
HETATM   26  C19 UNL     1      -6.020   2.893  -0.621  1.00  0.00           C  
HETATM   27  O8  UNL     1      -5.393   0.567  -0.555  1.00  0.00           O  
HETATM   28  C20 UNL     1      -1.762   1.224   0.283  1.00  0.00           C  
HETATM   29  C21 UNL     1      -1.850   2.106  -0.936  1.00  0.00           C  
HETATM   30  C22 UNL     1      -1.134   1.870   1.460  1.00  0.00           C  
HETATM   31  C23 UNL     1      -0.221   2.850   1.625  1.00  0.00           C  
HETATM   32  O9  UNL     1      -1.663   3.172   1.800  1.00  0.00           O  
HETATM   33  H1  UNL     1       7.718  -0.789  -1.275  1.00  0.00           H  
HETATM   34  H2  UNL     1       8.429   0.373  -0.121  1.00  0.00           H  
HETATM   35  H3  UNL     1       7.612   1.018  -1.603  1.00  0.00           H  
HETATM   36  H4  UNL     1       6.049   1.369   0.136  1.00  0.00           H  
HETATM   37  H5  UNL     1       6.364  -0.198   0.913  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.988   0.397  -1.739  1.00  0.00           H  
HETATM   39  H7  UNL     1       5.312  -1.315  -1.171  1.00  0.00           H  
HETATM   40  H8  UNL     1       1.719   0.025   1.274  1.00  0.00           H  
HETATM   41  H9  UNL     1       0.602   0.205  -1.496  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.602   1.390  -0.179  1.00  0.00           H  
HETATM   43  H11 UNL     1      -2.654  -0.970  -1.118  1.00  0.00           H  
HETATM   44  H12 UNL     1      -1.467  -0.126  -2.125  1.00  0.00           H  
HETATM   45  H13 UNL     1       0.166  -4.343  -1.751  1.00  0.00           H  
HETATM   46  H14 UNL     1       0.532  -3.809  -3.444  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.938  -4.842  -3.057  1.00  0.00           H  
HETATM   48  H16 UNL     1      -2.131  -1.327   1.224  1.00  0.00           H  
HETATM   49  H17 UNL     1      -0.500  -3.080   1.297  1.00  0.00           H  
HETATM   50  H18 UNL     1       3.049  -2.697   0.708  1.00  0.00           H  
HETATM   51  H19 UNL     1       1.980  -3.330  -0.553  1.00  0.00           H  
HETATM   52  H20 UNL     1       1.715  -3.852   1.167  1.00  0.00           H  
HETATM   53  H21 UNL     1      -1.258   1.269   3.559  1.00  0.00           H  
HETATM   54  H22 UNL     1      -3.440   1.691   2.772  1.00  0.00           H  
HETATM   55  H23 UNL     1      -4.442  -0.142   3.207  1.00  0.00           H  
HETATM   56  H24 UNL     1      -3.539  -0.064   0.468  1.00  0.00           H  
HETATM   57  H25 UNL     1      -6.699   2.583  -1.467  1.00  0.00           H  
HETATM   58  H26 UNL     1      -6.606   3.239   0.239  1.00  0.00           H  
HETATM   59  H27 UNL     1      -5.363   3.698  -1.023  1.00  0.00           H  
HETATM   60  H28 UNL     1      -1.013   1.826  -1.611  1.00  0.00           H  
HETATM   61  H29 UNL     1      -2.839   2.034  -1.401  1.00  0.00           H  
HETATM   62  H30 UNL     1      -1.668   3.153  -0.596  1.00  0.00           H  
HETATM   63  H31 UNL     1       0.147   3.522   0.822  1.00  0.00           H  
HETATM   64  H32 UNL     1       0.361   2.986   2.567  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4   38   39
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   17   40
CONECT    8    9   41   42
CONECT    9   10   15   28
CONECT   10   11   43   44
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   45   46   47
CONECT   15   16   19   48
CONECT   16   17   17   49
CONECT   17   18
CONECT   18   50   51   52
CONECT   19   20
CONECT   20   21   30   53
CONECT   21   22   23   54
CONECT   22   55
CONECT   23   24   28   56
CONECT   24   25
CONECT   25   26   27   27
CONECT   26   57   58   59
CONECT   28   29   30
CONECT   29   60   61   62
CONECT   30   31   32
CONECT   31   32   63   64
END

HMDB0038560
     RDKit          3D
8-Butanoylneosolaniol
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.5951    0.2143   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.3034   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344   -0.2718   -0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -0.1354   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0143    0.3990    1.1070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -0.5664   -0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906   -0.4625    0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4227    0.3202   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.0425   -0.0246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5890   -0.7701   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.9303   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -2.8068   -2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -3.9897   -2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419   -2.5300   -3.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -0.9374    1.1790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1749   -2.0808    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614   -1.8627    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886   -3.0202    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.2959    2.3765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    0.8788    2.5705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9911    0.7749    2.3364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5349   -0.3908    2.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500    0.8886    0.8275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9747    1.9862    0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336    1.7549   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    2.8926   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930    0.5666   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    1.2238    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8500    2.1062   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    1.8699    1.4602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2206    2.8495    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    3.1722    1.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179   -0.7887   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4288    0.3734   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121    1.0178   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492    1.3690    0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -0.1985    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9878    0.3970   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.3147   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193    0.0250    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6022    0.2054   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6021    1.3895   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6544   -0.9705   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -0.1264   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661   -4.3429   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -3.8094   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -4.8424   -3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1310   -1.3272    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4996   -3.0798    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.6966    0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -3.3301   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155   -3.8521    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.2693    3.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    1.6910    2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -0.1420    3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -0.0640    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6990    2.5826   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6055    3.2386    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3629    3.6980   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131    1.8261   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8393    2.0337   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.1532   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    3.5216    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    2.9861    2.5665 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  0
 17  7  1  0
 30 20  1  0
 28  9  1  0
 30 32  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  1
 16 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  1
 21 54  1  1
 22 55  1  0
 23 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 31 63  1  0
 31 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isopropyl butyric acid	HMDB
1-Methylethyl butanoate	HMDB
2-Propyl butanoate	HMDB
Butanoic acid, 1-methylethyl ester	HMDB
Butanoic acid, 2-methylethyl ester	HMDB
Butyric acid, isopropyl ester	HMDB
FEMA 2935	HMDB
Isopropyl butanoate	HMDB
Isopropyl N-butyrate	HMDB
N-Butyric acid isopropyl ester	HMDB
N-C3H7C(O)OCH(CH3)2	HMDB
(1's,2S,2'r,4's,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl butanoic acid	HMDB

Chemical Formula

C₂₃H₃₂O₉

Average Molecular Weight

452.4948

Monoisotopic Molecular Weight

452.204632622

IUPAC Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl butanoate

Traditional Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl butanoate

CAS Registry Number

98813-18-4

SMILES

[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCC

InChI Identifier

InChI=1S/C23H32O9/c1-6-7-17(26)31-15-9-22(10-28-13(3)24)16(8-12(15)2)32-20-18(27)19(30-14(4)25)21(22,5)23(20)11-29-23/h8,15-16,18-20,27H,6-7,9-11H2,1-5H3/t15-,16+,18+,19+,20+,21+,22+,23-/m0/s1

InChI Key

QAZLVSRKBUTUHB-MXINJKJASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Tricarboxylic acid or derivatives
Fatty acid ester
Oxepane
Oxane
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038560)

Source

Endogenous

Endogenous (HMDB: HMDB0038560)

Animal

Animal (HMDB: HMDB0038560)

Exogenous

Food

Food (HMDB: HMDB0038560)

Exogenous (HMDB: HMDB0038560)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038560)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038560)

Lipid metabolism pathway (HMDB: HMDB0038560)

Cellular process

Cell signaling (HMDB: HMDB0038560)

Biochemical process

Lipid transport (HMDB: HMDB0038560)

Role

Biological role

Energy source (HMDB: HMDB0038560)

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	0.62 g/L	ALOGPS
logP	1.69	ALOGPS
logP	0.73	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	108.99 m³·mol⁻¹	ChemAxon
Polarizability	46.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	202.032	31661259
DarkChem	[M-H]-	202.744	31661259
DeepCCS	[M-2H]-	232.768	30932474
DeepCCS	[M+Na]+	207.169	30932474
AllCCS	[M+H]+	204.8	32859911
AllCCS	[M+H-H2O]+	202.9	32859911
AllCCS	[M+NH4]+	206.6	32859911
AllCCS	[M+Na]+	207.0	32859911
AllCCS	[M-H]-	205.0	32859911
AllCCS	[M+Na-2H]-	206.0	32859911
AllCCS	[M+HCOO]-	207.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Butanoylneosolaniol	[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCC	3691.2	Standard polar	33892256
8-Butanoylneosolaniol	[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCC	2695.6	Standard non polar	33892256
8-Butanoylneosolaniol	[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCC	2798.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Butanoylneosolaniol,1TMS,isomer #1	CCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO2	2771.6	Semi standard non polar	33892256
8-Butanoylneosolaniol,1TBDMS,isomer #1	CCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO2	3008.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Butanoylneosolaniol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6149100000-745e7f953021e6f07ddd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Butanoylneosolaniol GC-MS (1 TMS) - 70eV, Positive	splash10-07i6-9043420000-4729fb3541aa7aa7acbf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Butanoylneosolaniol 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 - 8-Butanoylneosolaniol 10V, Positive-QTOF	splash10-0fdo-4109700000-e9f426f4ce7064c4b063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 20V, Positive-QTOF	splash10-00dl-5219100000-4f6ed4d53dd0d1fd9f15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 40V, Positive-QTOF	splash10-00dl-9207000000-b30b6eba9530d7c3ef30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 10V, Negative-QTOF	splash10-0zfu-4004900000-0da2b47e3b7309fe6051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 20V, Negative-QTOF	splash10-0a4l-9207400000-5a2ab7ae1796e5e87076	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 40V, Negative-QTOF	splash10-0a4j-6900000000-0ad2969149879a64ea16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 10V, Positive-QTOF	splash10-0a4i-0009100000-b94f1a0c58a87f9652b2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 20V, Positive-QTOF	splash10-0a4i-2009000000-1e90026a70a7386e1e1b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 40V, Positive-QTOF	splash10-0006-9002000000-628e00d2cd2b67d6c651	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 10V, Negative-QTOF	splash10-0q29-6009500000-6bbb8688288d5eb26526	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 20V, Negative-QTOF	splash10-0a4i-9001000000-849013160a134e7ebfc4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Butanoylneosolaniol 40V, Negative-QTOF	splash10-0006-9000000000-4849e5634093bdd63b85	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB017947

KNApSAcK ID

C00054163

Chemspider ID

23224543

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13797598

PDB ID

Not Available

ChEBI ID

168626

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 8-Butanoylneosolaniol (HMDB0038560)

MOL for HMDB0038560 (8-Butanoylneosolaniol)

3D MOL for HMDB0038560 (8-Butanoylneosolaniol)

3D SDF for HMDB0038560 (8-Butanoylneosolaniol)

3D-SDF for HMDB0038560 (8-Butanoylneosolaniol)

PDB for HMDB0038560 (8-Butanoylneosolaniol)

3D PDB for HMDB0038560 (8-Butanoylneosolaniol)

SMILES for HMDB0038560 (8-Butanoylneosolaniol)

INCHI for HMDB0038560 (8-Butanoylneosolaniol)

Structure for HMDB0038560 (8-Butanoylneosolaniol)

3D Structure for HMDB0038560 (8-Butanoylneosolaniol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra