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 17:37:06 UTC

Update Date

2022-03-07 02:52:34 UTC

HMDB ID

HMDB0030489

Secondary Accession Numbers

HMDB30489

Metabolite Identification

Common Name

Artonol C

Description

Artonol C belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Thus, artonol C is considered to be a flavonoid. Artonol C has been detected, but not quantified in, breadfruits (Artocarpus altilis) and fruits. This could make artonol C a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Artonol C.

Structure

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


  Mrv0541 05061305152D          

 37 42  0  0  0  0            999 V2000
   -2.1434   -0.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909    4.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    3.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962    3.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    2.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5489    3.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363    0.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    2.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508    2.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563    0.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308    0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    1.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600    1.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234    0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198    1.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326    1.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6032    3.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363    3.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6216   -0.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416    0.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0271    1.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013    2.6587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    2.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 20  2  0  0  0  0
 23 15  2  0  0  0  0
 23 22  1  0  0  0  0
 24 17  1  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 26 14  1  0  0  0  0
 26 21  2  0  0  0  0
 27 17  2  0  0  0  0
 27 22  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  2  0  0  0  0
 29  3  1  0  0  0  0
 29  4  1  0  0  0  0
 29  9  1  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 10  1  0  0  0  0
 31 18  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  2  0  0  0  0
 34 25  1  0  0  0  0
 35 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 19  1  0  0  0  0
 36 29  1  0  0  0  0
 37 28  1  0  0  0  0
 37 30  1  0  0  0  0
M  END

HMDB0030489
     RDKit          3D
Artonol C
 65 70  0  0  0  0  0  0  0  0999 V2000
   -3.6015   -3.7451   -2.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -3.3821   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -3.9440   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622   -2.3989   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -3.0221   -1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -2.0960   -1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.8771   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -0.0961   -0.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.4495   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893    0.4006    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0150    0.0258   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2945   -1.1951   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3160   -2.0519   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5255   -3.2849   -1.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740   -1.6722   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -2.5010   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -3.6071   -1.9379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8890    0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8302    2.1401    0.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6145    3.1413    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619    2.1008    2.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    2.5050    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    1.7009    0.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -0.4125   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    0.7815    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    1.5589    0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    1.2021    0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4765    0.4071    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.7566   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2911   -1.5636   -0.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -1.2033   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    0.8287    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0942    1.9960    1.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0489    2.8335    0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8994    1.6922    2.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.8118    1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    2.4347    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -3.3587   -3.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201   -4.4556   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -4.1797   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400   -3.2910    0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565   -4.9458   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -2.0308   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837   -3.5878   -2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.8134   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3097   -1.4820   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4977   -3.5751   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5316    2.6195   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8928    4.0181    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    3.4073   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.1656    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5546    2.0050    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    2.9548    2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    3.4494    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280    2.0118    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016    2.4044    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -1.2582   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7421    2.7741   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    2.4650    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9502    3.8770    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6926    2.4394    3.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6908    0.6464    2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9896    1.7229    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1099    3.7482    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    3.0781    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 28 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 36 37  2  0
 31  4  1  0
 16  6  1  0
 31 24  1  0
 15  9  1  0
 37 27  1  0
 23 10  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
 12 46  1  0
 14 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 26 56  1  0
 30 57  1  0
 34 58  1  0
 34 59  1  0
 34 60  1  0
 35 61  1  0
 35 62  1  0
 35 63  1  0
 36 64  1  0
 37 65  1  0
M  END


  Mrv0541 05061305152D          

 37 42  0  0  0  0            999 V2000
   -2.1434   -0.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909    4.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    3.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962    3.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    2.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5489    3.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363    0.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    2.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508    2.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563    0.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308    0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    1.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600    1.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234    0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198    1.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326    1.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6032    3.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363    3.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6216   -0.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416    0.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0271    1.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013    2.6587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    2.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 20  2  0  0  0  0
 23 15  2  0  0  0  0
 23 22  1  0  0  0  0
 24 17  1  0  0  0  0
 24 21  1  0  0  0  0
 25 20  1  0  0  0  0
 26 14  1  0  0  0  0
 26 21  2  0  0  0  0
 27 17  2  0  0  0  0
 27 22  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  2  0  0  0  0
 29  3  1  0  0  0  0
 29  4  1  0  0  0  0
 29  9  1  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 10  1  0  0  0  0
 31 18  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  2  0  0  0  0
 34 25  1  0  0  0  0
 35 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 19  1  0  0  0  0
 36 29  1  0  0  0  0
 37 28  1  0  0  0  0
 37 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030489

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31-32,34H,1,11H2,2-6H3

> <INCHI_KEY>
JVLAUHJNDLMVDW-UHFFFAOYSA-N

> <FORMULA>
C30H28O7

> <MOLECULAR_WEIGHT>
500.5391

> <EXACT_MASS>
500.18350325

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
54.36696112756263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
5.624142960333333

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.97480969293494

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.349415082879277

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590157019499547

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
142.77249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030489
     RDKit          3D
Artonol C
 65 70  0  0  0  0  0  0  0  0999 V2000
   -3.6015   -3.7451   -2.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -3.3821   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -3.9440   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622   -2.3989   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -3.0221   -1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -2.0960   -1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.8771   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -0.0961   -0.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.4495   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893    0.4006    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0150    0.0258   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2945   -1.1951   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3160   -2.0519   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5255   -3.2849   -1.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740   -1.6722   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -2.5010   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -3.6071   -1.9379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8890    0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8302    2.1401    0.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6145    3.1413    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619    2.1008    2.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    2.5050    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    1.7009    0.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -0.4125   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    0.7815    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    1.5589    0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    1.2021    0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4765    0.4071    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.7566   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2911   -1.5636   -0.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -1.2033   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    0.8287    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0942    1.9960    1.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0489    2.8335    0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8994    1.6922    2.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.8118    1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    2.4347    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -3.3587   -3.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201   -4.4556   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -4.1797   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400   -3.2910    0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565   -4.9458   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -2.0308   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837   -3.5878   -2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.8134   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3097   -1.4820   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4977   -3.5751   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5316    2.6195   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8928    4.0181    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    3.4073   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.1656    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5546    2.0050    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    2.9548    2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    3.4494    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280    2.0118    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016    2.4044    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -1.2582   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7421    2.7741   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    2.4650    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9502    3.8770    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6926    2.4394    3.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6908    0.6464    2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9896    1.7229    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1099    3.7482    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    3.0781    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 28 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 36 37  2  0
 31  4  1  0
 16  6  1  0
 31 24  1  0
 15  9  1  0
 37 27  1  0
 23 10  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
 12 46  1  0
 14 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 26 56  1  0
 30 57  1  0
 34 58  1  0
 34 59  1  0
 34 60  1  0
 35 61  1  0
 35 62  1  0
 35 63  1  0
 36 64  1  0
 37 65  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      -4.001  -0.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.152  -2.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.890   7.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.262   6.562   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.340   7.095   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.889   5.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.137   5.817   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.891   6.458   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.246   6.885   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.371   6.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.068   0.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.356   2.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.521  -0.590   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.507   4.322   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.521   4.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.412   0.478   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.177   1.119   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.246   1.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.986   3.895   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.782   1.973   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.767   1.760   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.672   3.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.042   4.536   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.657   0.692   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.261   2.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.397   3.254   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.808   2.614   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.631   3.895   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.726   6.458   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.481   5.817   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.616  -0.163   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.068   5.604   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.027  -0.803   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.371   1.332   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.917   3.681   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.096   4.963   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.111   4.322   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   29                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   30                                                            
CONECT    7    9   14                                                       
CONECT    8   10   15                                                       
CONECT    9    7   29                                                       
CONECT   10    8   30                                                       
CONECT   11   16   17                                                       
CONECT   12   18   19                                                       
CONECT   13    1    2   16                                                  
CONECT   14    7   19   26                                                  
CONECT   15    8   23   28                                                  
CONECT   16   11   13   20                                                  
CONECT   17   11   24   27                                                  
CONECT   18   12   21   31                                                  
CONECT   19   12   14   36                                                  
CONECT   20   16   22   25                                                  
CONECT   21   18   24   26                                                  
CONECT   22   20   23   27                                                  
CONECT   23   15   22   32                                                  
CONECT   24   17   21   33                                                  
CONECT   25   20   28   34                                                  
CONECT   26   14   21   35                                                  
CONECT   27   17   22   35                                                  
CONECT   28   15   25   37                                                  
CONECT   29    3    4    9   36                                             
CONECT   30    5    6   10   37                                             
CONECT   31   18                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
CONECT   34   25                                                            
CONECT   35   26   27                                                       
CONECT   36   19   29                                                       
CONECT   37   28   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

COMPND    HMDB0030489
HETATM    1  C1  UNL     1      -3.601  -3.745  -2.534  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.877  -3.382  -1.504  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.161  -3.944  -0.171  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.762  -2.399  -1.689  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.438  -3.022  -1.582  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.645  -2.096  -1.224  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.441  -0.877  -0.642  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.417  -0.096  -0.253  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.683  -0.449  -0.409  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.689   0.401   0.013  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.015   0.026  -0.152  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.295  -1.195  -0.738  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.316  -2.052  -1.163  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.525  -3.285  -1.756  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.974  -1.672  -0.996  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.973  -2.501  -1.406  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.200  -3.607  -1.938  1.00  0.00           O  
HETATM   18  O4  UNL     1       5.992   0.889   0.276  1.00  0.00           O  
HETATM   19  C15 UNL     1       5.830   2.140   0.872  1.00  0.00           C  
HETATM   20  C16 UNL     1       6.614   3.141   0.044  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.462   2.101   2.265  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.433   2.505   1.032  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.452   1.701   0.635  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.942  -0.412  -0.452  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.162   0.781   0.247  1.00  0.00           C  
HETATM   26  O5  UNL     1      -0.113   1.559   0.659  1.00  0.00           O  
HETATM   27  C22 UNL     1      -2.448   1.202   0.538  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.477   0.407   0.116  1.00  0.00           C  
HETATM   29  C24 UNL     1      -3.250  -0.757  -0.568  1.00  0.00           C  
HETATM   30  O6  UNL     1      -4.291  -1.564  -0.996  1.00  0.00           O  
HETATM   31  C25 UNL     1      -1.957  -1.203  -0.876  1.00  0.00           C  
HETATM   32  O7  UNL     1      -4.779   0.829   0.409  1.00  0.00           O  
HETATM   33  C26 UNL     1      -5.094   1.996   1.094  1.00  0.00           C  
HETATM   34  C27 UNL     1      -6.049   2.834   0.234  1.00  0.00           C  
HETATM   35  C28 UNL     1      -5.899   1.692   2.367  1.00  0.00           C  
HETATM   36  C29 UNL     1      -3.951   2.812   1.524  1.00  0.00           C  
HETATM   37  C30 UNL     1      -2.716   2.435   1.260  1.00  0.00           C  
HETATM   38  H1  UNL     1      -3.436  -3.359  -3.553  1.00  0.00           H  
HETATM   39  H2  UNL     1      -4.420  -4.456  -2.456  1.00  0.00           H  
HETATM   40  H3  UNL     1      -4.253  -4.180  -0.130  1.00  0.00           H  
HETATM   41  H4  UNL     1      -2.840  -3.291   0.658  1.00  0.00           H  
HETATM   42  H5  UNL     1      -2.656  -4.946  -0.083  1.00  0.00           H  
HETATM   43  H6  UNL     1      -1.836  -2.031  -2.784  1.00  0.00           H  
HETATM   44  H7  UNL     1      -0.184  -3.588  -2.530  1.00  0.00           H  
HETATM   45  H8  UNL     1      -0.408  -3.813  -0.750  1.00  0.00           H  
HETATM   46  H9  UNL     1       6.310  -1.482  -0.865  1.00  0.00           H  
HETATM   47  H10 UNL     1       5.498  -3.575  -1.885  1.00  0.00           H  
HETATM   48  H11 UNL     1       7.532   2.619  -0.299  1.00  0.00           H  
HETATM   49  H12 UNL     1       6.893   4.018   0.638  1.00  0.00           H  
HETATM   50  H13 UNL     1       5.982   3.407  -0.844  1.00  0.00           H  
HETATM   51  H14 UNL     1       6.086   1.166   2.761  1.00  0.00           H  
HETATM   52  H15 UNL     1       7.555   2.005   2.205  1.00  0.00           H  
HETATM   53  H16 UNL     1       6.115   2.955   2.871  1.00  0.00           H  
HETATM   54  H17 UNL     1       4.117   3.449   1.482  1.00  0.00           H  
HETATM   55  H18 UNL     1       2.428   2.012   0.771  1.00  0.00           H  
HETATM   56  H19 UNL     1      -0.102   2.404   1.148  1.00  0.00           H  
HETATM   57  H20 UNL     1      -5.230  -1.258  -0.784  1.00  0.00           H  
HETATM   58  H21 UNL     1      -5.742   2.774  -0.830  1.00  0.00           H  
HETATM   59  H22 UNL     1      -7.083   2.465   0.402  1.00  0.00           H  
HETATM   60  H23 UNL     1      -5.950   3.877   0.614  1.00  0.00           H  
HETATM   61  H24 UNL     1      -5.693   2.439   3.158  1.00  0.00           H  
HETATM   62  H25 UNL     1      -5.691   0.646   2.709  1.00  0.00           H  
HETATM   63  H26 UNL     1      -6.990   1.723   2.167  1.00  0.00           H  
HETATM   64  H27 UNL     1      -4.110   3.748   2.071  1.00  0.00           H  
HETATM   65  H28 UNL     1      -1.883   3.078   1.602  1.00  0.00           H  
CONECT    1    2    2   38   39
CONECT    2    3    4
CONECT    3   40   41   42
CONECT    4    5   31   43
CONECT    5    6   44   45
CONECT    6    7    7   16
CONECT    7    8   24
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   23
CONECT   11   12   12   18
CONECT   12   13   46
CONECT   13   14   15   15
CONECT   14   47
CONECT   15   16
CONECT   16   17   17
CONECT   18   19
CONECT   19   20   21   22
CONECT   20   48   49   50
CONECT   21   51   52   53
CONECT   22   23   23   54
CONECT   23   55
CONECT   24   25   25   31
CONECT   25   26   27
CONECT   26   56
CONECT   27   28   28   37
CONECT   28   29   32
CONECT   29   30   31   31
CONECT   30   57
CONECT   32   33
CONECT   33   34   35   36
CONECT   34   58   59   60
CONECT   35   61   62   63
CONECT   36   37   37   64
CONECT   37   65
END

HMDB0030489
     RDKit          3D
Artonol C
 65 70  0  0  0  0  0  0  0  0999 V2000
   -3.6015   -3.7451   -2.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -3.3821   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -3.9440   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622   -2.3989   -1.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -3.0221   -1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -2.0960   -1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.8771   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -0.0961   -0.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.4495   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893    0.4006    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0150    0.0258   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2945   -1.1951   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3160   -2.0519   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5255   -3.2849   -1.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740   -1.6722   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726   -2.5010   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -3.6071   -1.9379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8890    0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8302    2.1401    0.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6145    3.1413    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619    2.1008    2.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    2.5050    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    1.7009    0.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -0.4125   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    0.7815    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    1.5589    0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    1.2021    0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4765    0.4071    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2501   -0.7566   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2911   -1.5636   -0.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -1.2033   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788    0.8287    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0942    1.9960    1.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0489    2.8335    0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8994    1.6922    2.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.8118    1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    2.4347    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -3.3587   -3.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201   -4.4556   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -4.1797   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400   -3.2910    0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565   -4.9458   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -2.0308   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837   -3.5878   -2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080   -3.8134   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3097   -1.4820   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4977   -3.5751   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5316    2.6195   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8928    4.0181    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    3.4073   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.1656    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5546    2.0050    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    2.9548    2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1169    3.4494    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280    2.0118    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016    2.4044    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -1.2582   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7421    2.7741   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    2.4650    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9502    3.8770    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6926    2.4394    3.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6908    0.6464    2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9896    1.7229    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1099    3.7482    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    3.0781    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 28 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 36 37  2  0
 31  4  1  0
 16  6  1  0
 31 24  1  0
 15  9  1  0
 37 27  1  0
 23 10  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
 12 46  1  0
 14 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 26 56  1  0
 30 57  1  0
 34 58  1  0
 34 59  1  0
 34 60  1  0
 35 61  1  0
 35 62  1  0
 35 63  1  0
 36 64  1  0
 37 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,12-dihydro-6,10,15-Trihydroxy-3,3,12,12-tetramethyl-9-(1-methylethenyl)-3H,7H,8H-[1]benzopyrano[7,6-c]pyrano[3,2-H]xanthen-7-one	HMDB

Chemical Formula

C₃₀H₂₈O₇

Average Molecular Weight

500.5391

Monoisotopic Molecular Weight

500.18350325

IUPAC Name

3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one

Traditional Name

3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one

CAS Registry Number

186824-59-9

SMILES

CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O

InChI Identifier

InChI=1S/C30H28O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31-32,34H,1,11H2,2-6H3

InChI Key

JVLAUHJNDLMVDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Naphthopyranone
Naphthopyran
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Polyol
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111532 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030489)
Cell membrane (HMDB: HMDB0030489)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030489)

Source

Endogenous

Endogenous (HMDB: HMDB0030489)

Plant

Plant (HMDB: HMDB0030489)

Exogenous

Food

Food (HMDB: HMDB0030489)

Fruit

Tropical fruit

Breadfruit (FooDB: FOOD00309)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030489)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 184 °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	0.0044 g/L	ALOGPS
logP	5	ALOGPS
logP	5.62	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	142.77 m³·mol⁻¹	ChemAxon
Polarizability	54.37 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
DarkChem	[M+H]+	214.446	31661259
DarkChem	[M-H]-	212.967	31661259
DeepCCS	[M+H]+	216.354	30932474
DeepCCS	[M-H]-	213.959	30932474
DeepCCS	[M-2H]-	247.003	30932474
DeepCCS	[M+Na]+	222.267	30932474
AllCCS	[M+H]+	222.2	32859911
AllCCS	[M+H-H2O]+	220.1	32859911
AllCCS	[M+NH4]+	224.2	32859911
AllCCS	[M+Na]+	224.7	32859911
AllCCS	[M-H]-	218.4	32859911
AllCCS	[M+Na-2H]-	219.0	32859911
AllCCS	[M+HCOO]-	220.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.29 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4357 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3476.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	163.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	885.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	851.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	152.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1478.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	622.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1473.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	544.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	474.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	239.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artonol C	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O	5406.6	Standard polar	33892256
Artonol C	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O	3844.9	Standard non polar	33892256
Artonol C	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O	4210.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artonol C,1TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O)=C21	3956.6	Semi standard non polar	33892256
Artonol C,1TMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C21	3908.9	Semi standard non polar	33892256
Artonol C,1TMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C21	3948.8	Semi standard non polar	33892256
Artonol C,2TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C21	3835.5	Semi standard non polar	33892256
Artonol C,2TMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C21	3797.6	Semi standard non polar	33892256
Artonol C,2TMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C21	3814.0	Semi standard non polar	33892256
Artonol C,3TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C21	3776.3	Semi standard non polar	33892256
Artonol C,1TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O)=C21	4186.0	Semi standard non polar	33892256
Artonol C,1TBDMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C21	4117.1	Semi standard non polar	33892256
Artonol C,1TBDMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C21	4159.3	Semi standard non polar	33892256
Artonol C,2TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C21	4251.6	Semi standard non polar	33892256
Artonol C,2TBDMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C21	4193.6	Semi standard non polar	33892256
Artonol C,2TBDMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C21	4202.5	Semi standard non polar	33892256
Artonol C,3TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C21	4333.5	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 - Artonol C GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-0002900000-4804490c18510294e1a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artonol C GC-MS (2 TMS) - 70eV, Positive	splash10-00c0-2100329000-c0707026fa8bdc939626	2017-10-06	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 - Artonol C 10V, Positive-QTOF	splash10-0udi-1000790000-4a8c8253d87b4cfa1678	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 20V, Positive-QTOF	splash10-0f6x-0000910000-fae61f07f304d732689c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 40V, Positive-QTOF	splash10-014r-6005900000-c7eef290eb9c469b04b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 10V, Negative-QTOF	splash10-0002-0000900000-b2fd9fadad15c043aa25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 20V, Negative-QTOF	splash10-0002-0000900000-7c50a43d54579fdb3a1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 40V, Negative-QTOF	splash10-00lr-0006900000-d61cc44e173ffd6f8854	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 10V, Positive-QTOF	splash10-0udi-0000090000-cf99df1bcf26156d9ad0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 20V, Positive-QTOF	splash10-0udi-0000090000-cf99df1bcf26156d9ad0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 40V, Positive-QTOF	splash10-0uxr-0090250000-c029941dbf22259df5b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 10V, Negative-QTOF	splash10-0002-0000900000-ae7e5a7ce68f4f846e43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 20V, Negative-QTOF	splash10-0002-0000900000-ae7e5a7ce68f4f846e43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol C 40V, Negative-QTOF	splash10-00di-0249200000-823163c4501e82eabb6a	2021-09-23	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

FDB002358

KNApSAcK ID

C00013492

Chemspider ID

9014400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10839101

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1820391

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 Artonol C (HMDB0030489)

MOL for HMDB0030489 (Artonol C)

3D MOL for HMDB0030489 (Artonol C)

3D SDF for HMDB0030489 (Artonol C)

3D-SDF for HMDB0030489 (Artonol C)

PDB for HMDB0030489 (Artonol C)

3D PDB for HMDB0030489 (Artonol C)

SMILES for HMDB0030489 (Artonol C)

INCHI for HMDB0030489 (Artonol C)

Structure for HMDB0030489 (Artonol C)

3D Structure for HMDB0030489 (Artonol C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra