You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:13:58 UTC

Update Date

2022-03-07 02:53:44 UTC

HMDB ID

HMDB0033498

Secondary Accession Numbers

HMDB33498

Metabolite Identification

Common Name

Isonigerone

Description

Isonigerone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review very few articles have been published on Isonigerone.

Structure

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


  Mrv0541 05061307092D          

 42 47  0  0  0  0            999 V2000
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0  0  0  0
 13  7  2  0  0  0  0
 14  2  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 21 11  2  0  0  0  0
 22 12  2  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24 18  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29 23  1  0  0  0  0
 29 27  2  0  0  0  0
 30 25  2  0  0  0  0
 30 28  1  0  0  0  0
 31 24  1  0  0  0  0
 31 28  2  0  0  0  0
 32 26  2  0  0  0  0
 32 27  1  0  0  0  0
 33 19  2  0  0  0  0
 34 20  2  0  0  0  0
 35 29  1  0  0  0  0
 36 30  1  0  0  0  0
 37  3  1  0  0  0  0
 37 15  1  0  0  0  0
 38  4  1  0  0  0  0
 38 16  1  0  0  0  0
 39  5  1  0  0  0  0
 39 21  1  0  0  0  0
 40  6  1  0  0  0  0
 40 22  1  0  0  0  0
 41 13  1  0  0  0  0
 41 31  1  0  0  0  0
 42 14  1  0  0  0  0
 42 32  1  0  0  0  0
M  END

HMDB0033498
     RDKit          3D
Isonigerone
 68 73  0  0  0  0  0  0  0  0999 V2000
   -2.7380   -5.0450   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745   -3.9232   -0.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -2.6528   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063   -2.4023   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -1.1295   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872   -0.8344   -0.0259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4161   -1.8998   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420   -0.0873   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    1.2103    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.3466    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    2.2231    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671    3.5078    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767    3.7398    0.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    4.5287    0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    4.2317    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265    5.3393    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    3.0011   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053    2.0013   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697    0.7171   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315    0.4130   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    0.4409   -1.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    0.7608   -2.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240    0.1599   -2.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.1851   -3.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4657   -4.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -0.1120   -3.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -0.4266   -2.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714   -0.7432   -2.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -0.4307   -1.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.1585   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -0.1972    0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5133    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.7947    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6529   -1.1286    2.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5485    2.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -0.2696    2.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.3068    4.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.0029    4.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.0419    1.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    0.0898    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.2970   -0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -1.6103   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -5.8685   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -4.8528   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344   -5.4360   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -3.2222   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -2.5438   -0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985   -2.5488    0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4656   -1.5144   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6830    2.0269    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    5.5452    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383    5.4073   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    6.3140    0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    5.1559    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920    0.9673   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.0988   -4.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -0.4863   -3.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.0857   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   -1.7804   -2.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055   -1.0116    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -0.5318    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -2.1891    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142   -0.7993    3.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.0968    5.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.0123    3.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -0.7492    3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623    0.2643    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -1.7673   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 36 39  1  0
 39 40  2  0
 19 41  1  0
 41 42  2  0
 42  3  1  0
 41  8  1  0
 18 11  1  0
 40 20  1  0
 30 23  2  0
 40 31  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  7 47  1  0
  7 48  1  0
  7 49  1  0
 10 50  1  0
 14 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 22 55  1  0
 26 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 35 63  1  0
 38 64  1  0
 38 65  1  0
 38 66  1  0
 39 67  1  0
 42 68  1  0
M  END


  Mrv0541 05061307092D          

 42 47  0  0  0  0            999 V2000
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0  0  0  0
 13  7  2  0  0  0  0
 14  2  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 21 11  2  0  0  0  0
 22 12  2  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24 18  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29 23  1  0  0  0  0
 29 27  2  0  0  0  0
 30 25  2  0  0  0  0
 30 28  1  0  0  0  0
 31 24  1  0  0  0  0
 31 28  2  0  0  0  0
 32 26  2  0  0  0  0
 32 27  1  0  0  0  0
 33 19  2  0  0  0  0
 34 20  2  0  0  0  0
 35 29  1  0  0  0  0
 36 30  1  0  0  0  0
 37  3  1  0  0  0  0
 37 15  1  0  0  0  0
 38  4  1  0  0  0  0
 38 16  1  0  0  0  0
 39  5  1  0  0  0  0
 39 21  1  0  0  0  0
 40  6  1  0  0  0  0
 40 22  1  0  0  0  0
 41 13  1  0  0  0  0
 41 31  1  0  0  0  0
 42 14  1  0  0  0  0
 42 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033498

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O10/c1-13-7-20(34)28-30(36)25(18-10-16(38-4)12-22(40-6)24(18)31(28)41-13)26-17-9-15(37-3)11-21(39-5)23(17)29(35)27-19(33)8-14(2)42-32(26)27/h7-12,35-36H,1-6H3

> <INCHI_KEY>
CQWZRVPFGYDTKI-UHFFFAOYSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.5428

> <EXACT_MASS>
570.152597052

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
58.963888013980366

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxo-4H-benzo[h]chromen-6-yl}-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
5.4582238919999995

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.443381740741678

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.632769358760055

> <JCHEM_PKA_STRONGEST_BASIC>
-4.254065004744021

> <JCHEM_POLAR_SURFACE_AREA>
129.98000000000002

> <JCHEM_REFRACTIVITY>
156.00759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-6-yl}-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033498
     RDKit          3D
Isonigerone
 68 73  0  0  0  0  0  0  0  0999 V2000
   -2.7380   -5.0450   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745   -3.9232   -0.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -2.6528   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063   -2.4023   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -1.1295   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872   -0.8344   -0.0259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4161   -1.8998   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420   -0.0873   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    1.2103    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.3466    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    2.2231    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671    3.5078    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767    3.7398    0.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    4.5287    0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    4.2317    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265    5.3393    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    3.0011   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053    2.0013   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697    0.7171   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315    0.4130   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    0.4409   -1.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    0.7608   -2.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240    0.1599   -2.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.1851   -3.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4657   -4.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -0.1120   -3.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -0.4266   -2.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714   -0.7432   -2.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -0.4307   -1.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.1585   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -0.1972    0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5133    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.7947    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6529   -1.1286    2.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5485    2.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -0.2696    2.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.3068    4.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.0029    4.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.0419    1.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    0.0898    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.2970   -0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -1.6103   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -5.8685   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -4.8528   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344   -5.4360   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -3.2222   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -2.5438   -0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985   -2.5488    0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4656   -1.5144   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6830    2.0269    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    5.5452    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383    5.4073   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    6.3140    0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    5.1559    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920    0.9673   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.0988   -4.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -0.4863   -3.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.0857   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   -1.7804   -2.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055   -1.0116    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -0.5318    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -2.1891    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142   -0.7993    3.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.0968    5.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.0123    3.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -0.7492    3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623    0.2643    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -1.7673   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 36 39  1  0
 39 40  2  0
 19 41  1  0
 41 42  2  0
 42  3  1  0
 41  8  1  0
 18 11  1  0
 40 20  1  0
 30 23  2  0
 40 31  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  7 47  1  0
  7 48  1  0
  7 49  1  0
 10 50  1  0
 14 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 22 55  1  0
 26 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 35 63  1  0
 38 64  1  0
 38 65  1  0
 38 66  1  0
 39 67  1  0
 42 68  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       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   37                                                            
CONECT    4   38                                                            
CONECT    5   39                                                            
CONECT    6   40                                                            
CONECT    7   13   20                                                       
CONECT    8   14   19                                                       
CONECT    9   15   17                                                       
CONECT   10   16   18                                                       
CONECT   11   15   21                                                       
CONECT   12   16   22                                                       
CONECT   13    1    7   41                                                  
CONECT   14    2    8   42                                                  
CONECT   15    9   11   37                                                  
CONECT   16   10   12   38                                                  
CONECT   17    9   23   26                                                  
CONECT   18   10   24   25                                                  
CONECT   19    8   27   33                                                  
CONECT   20    7   28   34                                                  
CONECT   21   11   23   39                                                  
CONECT   22   12   24   40                                                  
CONECT   23   17   21   29                                                  
CONECT   24   18   22   31                                                  
CONECT   25   18   26   30                                                  
CONECT   26   17   25   32                                                  
CONECT   27   19   29   32                                                  
CONECT   28   20   30   31                                                  
CONECT   29   23   27   35                                                  
CONECT   30   25   28   36                                                  
CONECT   31   24   28   41                                                  
CONECT   32   26   27   42                                                  
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   29                                                            
CONECT   36   30                                                            
CONECT   37    3   15                                                       
CONECT   38    4   16                                                       
CONECT   39    5   21                                                       
CONECT   40    6   22                                                       
CONECT   41   13   31                                                       
CONECT   42   14   32                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

COMPND    HMDB0033498
HETATM    1  C1  UNL     1      -2.738  -5.045  -1.055  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.874  -3.923  -0.983  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.368  -2.653  -0.715  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.706  -2.402  -0.504  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.156  -1.129  -0.242  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.487  -0.834  -0.026  1.00  0.00           O  
HETATM    7  C5  UNL     1      -6.416  -1.900  -0.080  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.242  -0.087  -0.189  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.707   1.210   0.079  1.00  0.00           C  
HETATM   10  O3  UNL     1      -5.037   1.347   0.270  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.763   2.223   0.123  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.167   3.508   0.382  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.377   3.740   0.574  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.221   4.529   0.428  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.897   4.232   0.212  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.127   5.339   0.262  1.00  0.00           C  
HETATM   17  O5  UNL     1      -0.540   3.001  -0.033  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.405   2.001  -0.085  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.970   0.717  -0.348  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.432   0.413  -0.579  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.987   0.441  -1.858  1.00  0.00           C  
HETATM   22  O6  UNL     1       0.171   0.761  -2.935  1.00  0.00           O  
HETATM   23  C17 UNL     1       2.324   0.160  -2.084  1.00  0.00           C  
HETATM   24  C18 UNL     1       2.884   0.185  -3.343  1.00  0.00           C  
HETATM   25  O7  UNL     1       2.191   0.466  -4.333  1.00  0.00           O  
HETATM   26  C19 UNL     1       4.241  -0.112  -3.471  1.00  0.00           C  
HETATM   27  C20 UNL     1       5.016  -0.427  -2.360  1.00  0.00           C  
HETATM   28  C21 UNL     1       6.471  -0.743  -2.507  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.419  -0.431  -1.202  1.00  0.00           O  
HETATM   30  C22 UNL     1       3.142  -0.159  -1.021  1.00  0.00           C  
HETATM   31  C23 UNL     1       2.628  -0.197   0.265  1.00  0.00           C  
HETATM   32  C24 UNL     1       3.420  -0.513   1.346  1.00  0.00           C  
HETATM   33  O9  UNL     1       4.758  -0.795   1.125  1.00  0.00           O  
HETATM   34  C25 UNL     1       5.653  -1.129   2.171  1.00  0.00           C  
HETATM   35  C26 UNL     1       2.895  -0.549   2.618  1.00  0.00           C  
HETATM   36  C27 UNL     1       1.556  -0.270   2.862  1.00  0.00           C  
HETATM   37  O10 UNL     1       1.031  -0.307   4.147  1.00  0.00           O  
HETATM   38  C28 UNL     1      -0.360  -0.003   4.282  1.00  0.00           C  
HETATM   39  C29 UNL     1       0.797   0.042   1.756  1.00  0.00           C  
HETATM   40  C30 UNL     1       1.279   0.090   0.464  1.00  0.00           C  
HETATM   41  C31 UNL     1      -1.894  -0.297  -0.394  1.00  0.00           C  
HETATM   42  C32 UNL     1      -1.475  -1.610  -0.660  1.00  0.00           C  
HETATM   43  H1  UNL     1      -2.156  -5.869  -1.553  1.00  0.00           H  
HETATM   44  H2  UNL     1      -3.629  -4.853  -1.709  1.00  0.00           H  
HETATM   45  H3  UNL     1      -3.034  -5.436  -0.068  1.00  0.00           H  
HETATM   46  H4  UNL     1      -4.400  -3.222  -0.547  1.00  0.00           H  
HETATM   47  H5  UNL     1      -6.266  -2.544  -0.977  1.00  0.00           H  
HETATM   48  H6  UNL     1      -6.398  -2.549   0.813  1.00  0.00           H  
HETATM   49  H7  UNL     1      -7.466  -1.514  -0.158  1.00  0.00           H  
HETATM   50  H8  UNL     1      -5.683   2.027   0.454  1.00  0.00           H  
HETATM   51  H9  UNL     1      -2.560   5.545   0.636  1.00  0.00           H  
HETATM   52  H10 UNL     1       0.638   5.407  -0.721  1.00  0.00           H  
HETATM   53  H11 UNL     1      -0.375   6.314   0.432  1.00  0.00           H  
HETATM   54  H12 UNL     1       0.896   5.156   1.018  1.00  0.00           H  
HETATM   55  H13 UNL     1      -0.792   0.967  -2.791  1.00  0.00           H  
HETATM   56  H14 UNL     1       4.706  -0.099  -4.448  1.00  0.00           H  
HETATM   57  H15 UNL     1       6.761  -0.486  -3.552  1.00  0.00           H  
HETATM   58  H16 UNL     1       7.002  -0.086  -1.774  1.00  0.00           H  
HETATM   59  H17 UNL     1       6.714  -1.780  -2.227  1.00  0.00           H  
HETATM   60  H18 UNL     1       6.705  -1.012   1.815  1.00  0.00           H  
HETATM   61  H19 UNL     1       5.494  -0.532   3.076  1.00  0.00           H  
HETATM   62  H20 UNL     1       5.485  -2.189   2.415  1.00  0.00           H  
HETATM   63  H21 UNL     1       3.514  -0.799   3.486  1.00  0.00           H  
HETATM   64  H22 UNL     1      -0.607  -0.097   5.346  1.00  0.00           H  
HETATM   65  H23 UNL     1      -0.600   1.012   3.920  1.00  0.00           H  
HETATM   66  H24 UNL     1      -0.881  -0.749   3.631  1.00  0.00           H  
HETATM   67  H25 UNL     1      -0.262   0.264   1.941  1.00  0.00           H  
HETATM   68  H26 UNL     1      -0.426  -1.767  -0.819  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3
CONECT    3    4    4   42
CONECT    4    5   46
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   47   48   49
CONECT    8    9   41
CONECT    9   10   11   11
CONECT   10   50
CONECT   11   12   18
CONECT   12   13   13   14
CONECT   14   15   15   51
CONECT   15   16   17
CONECT   16   52   53   54
CONECT   17   18
CONECT   18   19   19
CONECT   19   20   41
CONECT   20   21   21   40
CONECT   21   22   23
CONECT   22   55
CONECT   23   24   30   30
CONECT   24   25   25   26
CONECT   26   27   27   56
CONECT   27   28   29
CONECT   28   57   58   59
CONECT   29   30
CONECT   30   31
CONECT   31   32   32   40
CONECT   32   33   35
CONECT   33   34
CONECT   34   60   61   62
CONECT   35   36   36   63
CONECT   36   37   39
CONECT   37   38
CONECT   38   64   65   66
CONECT   39   40   40   67
CONECT   41   42   42
CONECT   42   68
END

HMDB0033498
     RDKit          3D
Isonigerone
 68 73  0  0  0  0  0  0  0  0999 V2000
   -2.7380   -5.0450   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745   -3.9232   -0.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -2.6528   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063   -2.4023   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -1.1295   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4872   -0.8344   -0.0259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4161   -1.8998   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420   -0.0873   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    1.2103    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    1.3466    0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    2.2231    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1671    3.5078    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767    3.7398    0.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    4.5287    0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    4.2317    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265    5.3393    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    3.0011   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053    2.0013   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697    0.7171   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315    0.4130   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    0.4409   -1.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    0.7608   -2.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240    0.1599   -2.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.1851   -3.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4657   -4.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -0.1120   -3.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -0.4266   -2.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714   -0.7432   -2.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186   -0.4307   -1.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.1585   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -0.1972    0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5133    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.7947    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6529   -1.1286    2.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5485    2.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -0.2696    2.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.3068    4.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.0029    4.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.0419    1.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    0.0898    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.2970   -0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -1.6103   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -5.8685   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -4.8528   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344   -5.4360   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002   -3.2222   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -2.5438   -0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985   -2.5488    0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4656   -1.5144   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6830    2.0269    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    5.5452    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6383    5.4073   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    6.3140    0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    5.1559    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920    0.9673   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058   -0.0988   -4.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614   -0.4863   -3.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.0857   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   -1.7804   -2.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055   -1.0116    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -0.5318    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -2.1891    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142   -0.7993    3.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.0968    5.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.0123    3.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -0.7492    3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623    0.2643    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -1.7673   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 36 39  1  0
 39 40  2  0
 19 41  1  0
 41 42  2  0
 42  3  1  0
 41  8  1  0
 18 11  1  0
 40 20  1  0
 30 23  2  0
 40 31  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  7 47  1  0
  7 48  1  0
  7 49  1  0
 10 50  1  0
 14 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 22 55  1  0
 26 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 35 63  1  0
 38 64  1  0
 38 65  1  0
 38 66  1  0
 39 67  1  0
 42 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₀

Average Molecular Weight

570.5428

Monoisotopic Molecular Weight

570.152597052

IUPAC Name

5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxo-4H-benzo[h]chromen-6-yl}-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-6-yl}-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1

InChI Identifier

InChI=1S/C32H26O10/c1-13-7-20(34)28-30(36)25(18-10-16(38-4)12-22(40-6)24(18)31(28)41-13)26-17-9-15(37-3)11-21(39-5)23(17)29(35)27-19(33)8-14(2)42-32(26)27/h7-12,35-36H,1-6H3

InChI Key

CQWZRVPFGYDTKI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Chromone
1-naphthol
2-naphthol
Benzopyran
1-benzopyran
Naphthalene
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033498)

Cellular substructure

Membrane (HMDB: HMDB0033498)

Source

Exogenous

Food

Food (HMDB: HMDB0033498)

Not Available

Nutrient (HMDB: HMDB0033498)

Environmental role

Environmental contaminant (HMDB: HMDB0033498)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	330 °C	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	0.0043 g/L	ALOGPS
logP	4.24	ALOGPS
logP	5.46	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	129.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.01 m³·mol⁻¹	ChemAxon
Polarizability	58.96 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
DeepCCS	[M+H]+	232.454	30932474
DeepCCS	[M-H]-	230.558	30932474
DeepCCS	[M-2H]-	263.799	30932474
DeepCCS	[M+Na]+	238.118	30932474
AllCCS	[M+H]+	231.5	32859911
AllCCS	[M+H-H2O]+	229.6	32859911
AllCCS	[M+NH4]+	233.1	32859911
AllCCS	[M+Na]+	233.6	32859911
AllCCS	[M-H]-	226.1	32859911
AllCCS	[M+Na-2H]-	226.8	32859911
AllCCS	[M+HCOO]-	227.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isonigerone	COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1	6848.2	Standard polar	33892256
Isonigerone	COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1	4502.8	Standard non polar	33892256
Isonigerone	COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1	5007.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isonigerone,1TMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	4994.2	Semi standard non polar	33892256
Isonigerone,1TMS,isomer #2	COC1=CC(OC)=C2C(O)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	5017.6	Semi standard non polar	33892256
Isonigerone,2TMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	4841.7	Semi standard non polar	33892256
Isonigerone,1TBDMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	5139.7	Semi standard non polar	33892256
Isonigerone,1TBDMS,isomer #2	COC1=CC(OC)=C2C(O)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C(C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	5150.7	Semi standard non polar	33892256
Isonigerone,2TBDMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C(C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C1	5223.7	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 - Isonigerone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0000090000-6b618df2218274dc9f49	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2000069000-313c71ebe0372915596e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS ("Isonigerone,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	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 - Isonigerone 10V, Positive-QTOF	splash10-00di-0000090000-1f1e2b270cf2b60eba10	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 20V, Positive-QTOF	splash10-0fki-0000090000-f8779ba1168344f03278	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 40V, Positive-QTOF	splash10-05vk-0000690000-1172c03afaf8dd491557	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 10V, Negative-QTOF	splash10-014i-0000090000-e3a63a894161036df176	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 20V, Negative-QTOF	splash10-0gb9-0000090000-374834fd1633bff2d752	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 40V, Negative-QTOF	splash10-00di-1000590000-b775b3f21e72d305ed44	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 10V, Positive-QTOF	splash10-00di-0000090000-19d2aaec626c05e425d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 20V, Positive-QTOF	splash10-00di-0000090000-80fd1f0a608d2482691a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 40V, Positive-QTOF	splash10-0a4r-0000490000-26225eebb9a0027617f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 10V, Negative-QTOF	splash10-014i-0000090000-d0c1e2d0c0af858f93c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 20V, Negative-QTOF	splash10-014i-0000090000-d0c1e2d0c0af858f93c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonigerone 40V, Negative-QTOF	splash10-08fr-0000190000-042a50e5566e89e2dcbb	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB011550

KNApSAcK ID

Not Available

Chemspider ID

30777012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101278413

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isonigerone (HMDB0033498)

MOL for HMDB0033498 (Isonigerone)

3D MOL for HMDB0033498 (Isonigerone)

3D SDF for HMDB0033498 (Isonigerone)

3D-SDF for HMDB0033498 (Isonigerone)

PDB for HMDB0033498 (Isonigerone)

3D PDB for HMDB0033498 (Isonigerone)

SMILES for HMDB0033498 (Isonigerone)

INCHI for HMDB0033498 (Isonigerone)

Structure for HMDB0033498 (Isonigerone)

3D Structure for HMDB0033498 (Isonigerone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra