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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:01:49 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033316

Secondary Accession Numbers

HMDB33316

Metabolite Identification

Common Name

Garcinone E

Description

Garcinone E belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Garcinone E has been detected, but not quantified in, fruits and purple mangosteens (Garcinia mangostana). This could make garcinone e a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Garcinone E.

Structure

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


  Mrv0541 05061307032D          

 34 36  0  0  0  0            999 V2000
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    5.0013    2.0625    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
    1.4289    0.8250    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
    3.5724    1.2375    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    2.0625    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
    0.7145    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
    2.1434    1.2375    0.0000 C   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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  2  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24 17  2  0  0  0  0
 24 23  1  0  0  0  0
 25 18  2  0  0  0  0
 26 19  2  0  0  0  0
 26 25  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  2  0  0  0  0
 29 20  1  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32 26  1  0  0  0  0
 33 27  2  0  0  0  0
 34 21  1  0  0  0  0
 34 28  1  0  0  0  0
M  END

HMDB0033316
     RDKit          3D
Garcinone E
 66 68  0  0  0  0  0  0  0  0999 V2000
    7.3688   -0.8472    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -1.0804    1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4387   -2.0115    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.4467    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8634   -0.5359    2.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.7925    1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666   -2.0200    1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -3.1559    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927   -2.1758    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172   -1.0900   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -1.2152   -0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945   -0.2653   -1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.5096   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -1.8909   -2.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -2.7998   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -3.9399   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -4.3356   -2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -4.8511   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514    0.5334   -2.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0934    0.2051   -3.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    1.7911   -2.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    2.8233   -2.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    2.0862   -1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    3.4747   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    3.6921    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003    4.6542    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593    5.6511   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762    4.7645    1.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    1.0353   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842    1.2086    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.3396    0.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    0.1387    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494    0.3463    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601    1.5438    1.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.3124    1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7051   -1.8430    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0019   -0.2697    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.7654    3.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816   -3.0877    2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5084   -1.9653    3.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.2550    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496    0.3798    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.3665    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903   -3.0093    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -3.1647   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378   -2.2810   -2.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0410   -1.8712   -3.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.5345   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -4.3409   -3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -3.7416   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606   -5.4068   -1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -5.8859   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -4.6503   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.7379    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116    0.9389   -3.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    2.8027   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    4.1738   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171    3.8187   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.9783    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5227    5.9738   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593    5.2990   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091    6.5326   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    5.0965    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    3.7598    2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473    5.4491    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.4510    1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33  6  1  0
 32 10  1  0
 29 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
  9 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 20 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 34 66  1  0
M  END


  Mrv0541 05061307032D          

 34 36  0  0  0  0            999 V2000
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    5.0013    2.0625    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
    1.4289    0.8250    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
    3.5724    1.2375    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    2.0625    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
    0.7145    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
    2.1434    1.2375    0.0000 C   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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  2  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24 17  2  0  0  0  0
 24 23  1  0  0  0  0
 25 18  2  0  0  0  0
 26 19  2  0  0  0  0
 26 25  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 19  1  0  0  0  0
 28 22  2  0  0  0  0
 29 20  1  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32 26  1  0  0  0  0
 33 27  2  0  0  0  0
 34 21  1  0  0  0  0
 34 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033316

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(O)C(O)=C3CC=C(C)C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O6/c1-14(2)7-10-17-20(29)13-21-23(24(17)30)27(33)22-18(11-8-15(3)4)25(31)26(32)19(28(22)34-21)12-9-16(5)6/h7-9,13,29-32H,10-12H2,1-6H3

> <INCHI_KEY>
WVJYEKGQSBGNRP-UHFFFAOYSA-N

> <FORMULA>
C28H32O6

> <MOLECULAR_WEIGHT>
464.5501

> <EXACT_MASS>
464.219888756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
52.89416526208363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,6,8-tetrahydroxy-1,4,7-tris(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
7.581079931666667

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.677910129674154

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.0618452210078475

> <JCHEM_PKA_STRONGEST_BASIC>
-4.232218157753214

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
137.46829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
garcinone E

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033316
     RDKit          3D
Garcinone E
 66 68  0  0  0  0  0  0  0  0999 V2000
    7.3688   -0.8472    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -1.0804    1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4387   -2.0115    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.4467    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8634   -0.5359    2.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.7925    1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666   -2.0200    1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -3.1559    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927   -2.1758    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172   -1.0900   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -1.2152   -0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945   -0.2653   -1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.5096   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -1.8909   -2.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -2.7998   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -3.9399   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -4.3356   -2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -4.8511   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514    0.5334   -2.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0934    0.2051   -3.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    1.7911   -2.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    2.8233   -2.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    2.0862   -1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    3.4747   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    3.6921    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003    4.6542    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593    5.6511   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762    4.7645    1.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    1.0353   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842    1.2086    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.3396    0.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    0.1387    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494    0.3463    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601    1.5438    1.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.3124    1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7051   -1.8430    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0019   -0.2697    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.7654    3.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816   -3.0877    2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5084   -1.9653    3.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.2550    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496    0.3798    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.3665    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903   -3.0093    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -3.1647   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378   -2.2810   -2.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0410   -1.8712   -3.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.5345   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -4.3409   -3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -3.7416   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606   -5.4068   -1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -5.8859   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -4.6503   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.7379    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116    0.9389   -3.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    2.8027   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    4.1738   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171    3.8187   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.9783    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5227    5.9738   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593    5.2990   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091    6.5326   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    5.0965    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    3.7598    2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473    5.4491    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.4510    1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33  6  1  0
 32 10  1  0
 29 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
  9 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 20 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 34 66  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      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6   16                                                            
CONECT    7   10   14                                                       
CONECT    8   11   15                                                       
CONECT    9   12   16                                                       
CONECT   10    7   17                                                       
CONECT   11    8   18                                                       
CONECT   12    9   19                                                       
CONECT   13   20   21                                                       
CONECT   14    1    2    7                                                  
CONECT   15    3    4    8                                                  
CONECT   16    5    6    9                                                  
CONECT   17   10   20   24                                                  
CONECT   18   11   22   25                                                  
CONECT   19   12   26   28                                                  
CONECT   20   13   17   29                                                  
CONECT   21   13   23   34                                                  
CONECT   22   18   27   28                                                  
CONECT   23   21   24   27                                                  
CONECT   24   17   23   30                                                  
CONECT   25   18   26   31                                                  
CONECT   26   19   25   32                                                  
CONECT   27   22   23   33                                                  
CONECT   28   19   22   34                                                  
CONECT   29   20                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   26                                                            
CONECT   33   27                                                            
CONECT   34   21   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

COMPND    HMDB0033316
HETATM    1  C1  UNL     1       7.369  -0.847   0.951  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.214  -1.080   1.907  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.439  -2.012   3.031  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.092  -0.447   1.728  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.863  -0.536   2.535  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.722  -0.793   1.623  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.467  -2.020   1.126  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.239  -3.156   1.453  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.393  -2.176   0.254  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.617  -1.090  -0.084  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.388  -1.215  -0.896  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.194  -0.265  -1.292  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.233  -0.510  -2.155  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.444  -1.891  -2.656  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.053  -2.800  -1.652  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.473  -3.940  -1.382  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.228  -4.336  -2.060  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.067  -4.851  -0.381  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.051   0.533  -2.533  1.00  0.00           C  
HETATM   20  O3  UNL     1      -4.093   0.205  -3.417  1.00  0.00           O  
HETATM   21  C18 UNL     1      -2.830   1.791  -2.056  1.00  0.00           C  
HETATM   22  O4  UNL     1      -3.649   2.823  -2.437  1.00  0.00           O  
HETATM   23  C19 UNL     1      -1.786   2.086  -1.178  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.608   3.475  -0.693  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.525   3.692   0.450  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.400   4.654   0.540  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.559   5.651  -0.526  1.00  0.00           C  
HETATM   28  C24 UNL     1      -4.276   4.765   1.751  1.00  0.00           C  
HETATM   29  C25 UNL     1      -0.973   1.035  -0.804  1.00  0.00           C  
HETATM   30  C26 UNL     1       0.084   1.209   0.062  1.00  0.00           C  
HETATM   31  O5  UNL     1       0.298   2.340   0.508  1.00  0.00           O  
HETATM   32  C27 UNL     1       0.894   0.139   0.431  1.00  0.00           C  
HETATM   33  C28 UNL     1       1.949   0.346   1.302  1.00  0.00           C  
HETATM   34  O6  UNL     1       2.260   1.544   1.836  1.00  0.00           O  
HETATM   35  H1  UNL     1       8.162  -0.312   1.492  1.00  0.00           H  
HETATM   36  H2  UNL     1       7.705  -1.843   0.556  1.00  0.00           H  
HETATM   37  H3  UNL     1       7.002  -0.270   0.094  1.00  0.00           H  
HETATM   38  H4  UNL     1       5.826  -1.765   3.915  1.00  0.00           H  
HETATM   39  H5  UNL     1       6.282  -3.088   2.760  1.00  0.00           H  
HETATM   40  H6  UNL     1       7.508  -1.965   3.360  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.024   0.255   0.869  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.650   0.380   3.110  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.940  -1.367   3.299  1.00  0.00           H  
HETATM   44  H10 UNL     1       3.990  -3.009   2.095  1.00  0.00           H  
HETATM   45  H11 UNL     1       1.203  -3.165  -0.134  1.00  0.00           H  
HETATM   46  H12 UNL     1      -1.438  -2.281  -2.902  1.00  0.00           H  
HETATM   47  H13 UNL     1      -3.041  -1.871  -3.600  1.00  0.00           H  
HETATM   48  H14 UNL     1      -3.981  -2.534  -1.131  1.00  0.00           H  
HETATM   49  H15 UNL     1      -1.444  -4.341  -3.173  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.346  -3.742  -1.847  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.961  -5.407  -1.829  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.978  -5.886  -0.714  1.00  0.00           H  
HETATM   53  H19 UNL     1      -4.145  -4.650  -0.204  1.00  0.00           H  
HETATM   54  H20 UNL     1      -2.537  -4.738   0.588  1.00  0.00           H  
HETATM   55  H21 UNL     1      -4.712   0.939  -3.716  1.00  0.00           H  
HETATM   56  H22 UNL     1      -4.436   2.803  -3.050  1.00  0.00           H  
HETATM   57  H23 UNL     1      -2.007   4.174  -1.560  1.00  0.00           H  
HETATM   58  H24 UNL     1      -0.617   3.819  -0.447  1.00  0.00           H  
HETATM   59  H25 UNL     1      -2.459   2.978   1.291  1.00  0.00           H  
HETATM   60  H26 UNL     1      -2.523   5.974  -0.837  1.00  0.00           H  
HETATM   61  H27 UNL     1      -4.059   5.299  -1.438  1.00  0.00           H  
HETATM   62  H28 UNL     1      -4.109   6.533  -0.104  1.00  0.00           H  
HETATM   63  H29 UNL     1      -5.269   5.097   1.430  1.00  0.00           H  
HETATM   64  H30 UNL     1      -4.413   3.760   2.228  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.847   5.449   2.491  1.00  0.00           H  
HETATM   66  H32 UNL     1       1.961   2.451   1.824  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4    4
CONECT    3   38   39   40
CONECT    4    5   41
CONECT    5    6   42   43
CONECT    6    7    7   33
CONECT    7    8    9
CONECT    8   44
CONECT    9   10   10   45
CONECT   10   11   32
CONECT   11   12
CONECT   12   13   13   29
CONECT   13   14   19
CONECT   14   15   46   47
CONECT   15   16   16   48
CONECT   16   17   18
CONECT   17   49   50   51
CONECT   18   52   53   54
CONECT   19   20   21   21
CONECT   20   55
CONECT   21   22   23
CONECT   22   56
CONECT   23   24   29   29
CONECT   24   25   57   58
CONECT   25   26   26   59
CONECT   26   27   28
CONECT   27   60   61   62
CONECT   28   63   64   65
CONECT   29   30
CONECT   30   31   31   32
CONECT   32   33   33
CONECT   33   34
CONECT   34   66
END

HMDB0033316
     RDKit          3D
Garcinone E
 66 68  0  0  0  0  0  0  0  0999 V2000
    7.3688   -0.8472    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -1.0804    1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4387   -2.0115    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.4467    1.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8634   -0.5359    2.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.7925    1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666   -2.0200    1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -3.1559    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927   -2.1758    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172   -1.0900   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -1.2152   -0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945   -0.2653   -1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.5096   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -1.8909   -2.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -2.7998   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -3.9399   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -4.3356   -2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -4.8511   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514    0.5334   -2.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0934    0.2051   -3.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    1.7911   -2.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    2.8233   -2.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    2.0862   -1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    3.4747   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    3.6921    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003    4.6542    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593    5.6511   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762    4.7645    1.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    1.0353   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842    1.2086    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.3396    0.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    0.1387    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494    0.3463    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601    1.5438    1.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.3124    1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7051   -1.8430    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0019   -0.2697    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.7654    3.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816   -3.0877    2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5084   -1.9653    3.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.2550    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496    0.3798    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.3665    3.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903   -3.0093    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -3.1647   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378   -2.2810   -2.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0410   -1.8712   -3.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.5345   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -4.3409   -3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -3.7416   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606   -5.4068   -1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -5.8859   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -4.6503   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -4.7379    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116    0.9389   -3.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    2.8027   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    4.1738   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171    3.8187   -0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.9783    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5227    5.9738   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593    5.2990   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091    6.5326   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    5.0965    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    3.7598    2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473    5.4491    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.4510    1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33  6  1  0
 32 10  1  0
 29 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  8 44  1  0
  9 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 20 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 34 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Garcinone e	MeSH

Chemical Formula

C₂₈H₃₂O₆

Average Molecular Weight

464.5501

Monoisotopic Molecular Weight

464.219888756

IUPAC Name

2,3,6,8-tetrahydroxy-1,4,7-tris(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

garcinone E

CAS Registry Number

112649-21-5

SMILES

CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(O)C(O)=C3CC=C(C)C)C=C1O

InChI Identifier

InChI=1S/C28H32O6/c1-14(2)7-10-17-20(29)13-21-23(24(17)30)27(33)22-18(11-8-15(3)4)25(31)26(32)19(28(22)34-21)12-9-16(5)6/h7-9,13,29-32H,10-12H2,1-6H3

InChI Key

WVJYEKGQSBGNRP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

8-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
4-prenylated xanthone
8-prenylated xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033316)

Cellular substructure

Membrane (HMDB: HMDB0033316)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033316)

Source

Exogenous

Food

Food (HMDB: HMDB0033316)

Fruit

Tropical fruit

Purple mangosteen (FooDB: FOOD00406)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033316)

Not Available

Nutrient (HMDB: HMDB0033316)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152.5 - 155.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.7e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	5.15	ALOGPS
logP	7.58	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.06	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.47 m³·mol⁻¹	ChemAxon
Polarizability	52.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	213.184	30932474
DeepCCS	[M-H]-	210.788	30932474
DeepCCS	[M-2H]-	243.726	30932474
DeepCCS	[M+Na]+	219.136	30932474
AllCCS	[M+H]+	214.3	32859911
AllCCS	[M+H-H2O]+	212.1	32859911
AllCCS	[M+NH4]+	216.3	32859911
AllCCS	[M+Na]+	216.9	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	203.9	32859911
AllCCS	[M+HCOO]-	204.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Garcinone E	CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(O)C(O)=C3CC=C(C)C)C=C1O	5765.9	Standard polar	33892256
Garcinone E	CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(O)C(O)=C3CC=C(C)C)C=C1O	3932.2	Standard non polar	33892256
Garcinone E	CC(C)=CCC1=C(O)C2=C(OC3=C(C2=O)C(CC=C(C)C)=C(O)C(O)=C3CC=C(C)C)C=C1O	3852.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Garcinone E,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3770.2	Semi standard non polar	33892256
Garcinone E,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	3798.8	Semi standard non polar	33892256
Garcinone E,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	3799.0	Semi standard non polar	33892256
Garcinone E,1TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	3834.3	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3698.8	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3643.3	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3630.8	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	3692.4	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #5	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	3679.3	Semi standard non polar	33892256
Garcinone E,2TMS,isomer #6	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	3705.3	Semi standard non polar	33892256
Garcinone E,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3645.5	Semi standard non polar	33892256
Garcinone E,3TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3644.1	Semi standard non polar	33892256
Garcinone E,3TMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3569.3	Semi standard non polar	33892256
Garcinone E,3TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	3595.4	Semi standard non polar	33892256
Garcinone E,4TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C	3636.0	Semi standard non polar	33892256
Garcinone E,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4001.1	Semi standard non polar	33892256
Garcinone E,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	4019.6	Semi standard non polar	33892256
Garcinone E,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	4019.4	Semi standard non polar	33892256
Garcinone E,1TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	4052.2	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4145.8	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4096.7	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4085.2	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	4146.3	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #5	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	4154.4	Semi standard non polar	33892256
Garcinone E,2TBDMS,isomer #6	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O	4154.4	Semi standard non polar	33892256
Garcinone E,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4276.9	Semi standard non polar	33892256
Garcinone E,3TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4277.5	Semi standard non polar	33892256
Garcinone E,3TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4180.6	Semi standard non polar	33892256
Garcinone E,3TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O	4264.6	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 - Garcinone E GC-MS (Non-derivatized) - 70eV, Positive	splash10-0592-1001900000-da6d71b52c792c3f4614	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Garcinone E GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1000009000-f18ac36d51c35163189d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Garcinone E GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Garcinone E LC-ESI-qTof , Positive-QTOF	splash10-0229-0922100000-0fc0c80ba046be0a1ca9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Garcinone E , positive-QTOF	splash10-0f6t-0396100000-6015b8aa4febecfe05bc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 10V, Positive-QTOF	splash10-01b9-0000900000-b0cf1de01ae8f307acb6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 20V, Positive-QTOF	splash10-0pvi-2005900000-f215d30e586ed4312cf3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 40V, Positive-QTOF	splash10-0uy0-4019300000-130aff11a7986f01fdab	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 10V, Negative-QTOF	splash10-03di-0000900000-86d2bf16e0b2affff444	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 20V, Negative-QTOF	splash10-03di-0004900000-cfcf925df6a11a2e246b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 40V, Negative-QTOF	splash10-004m-0429500000-7aea2e927f39c0434943	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 10V, Negative-QTOF	splash10-03di-0000900000-c2f336ffe0bfffbff616	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 20V, Negative-QTOF	splash10-03di-0000900000-fb3e1136e3a055ca9170	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 40V, Negative-QTOF	splash10-0035-6018900000-f789f48f834cd82d52fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 10V, Positive-QTOF	splash10-1000-0006900000-1ca5c8ace4c56ca47d45	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 20V, Positive-QTOF	splash10-0zfr-0009800000-60b8d88ad9b82f89b467	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Garcinone E 40V, Positive-QTOF	splash10-0udu-0009000000-0f637198c920c6c86413	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

FDB011340

KNApSAcK ID

C00030359

Chemspider ID

8473979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10298511

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834741

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 Garcinone E (HMDB0033316)

MOL for HMDB0033316 (Garcinone E)

3D MOL for HMDB0033316 (Garcinone E)

3D SDF for HMDB0033316 (Garcinone E)

3D-SDF for HMDB0033316 (Garcinone E)

PDB for HMDB0033316 (Garcinone E)

3D PDB for HMDB0033316 (Garcinone E)

SMILES for HMDB0033316 (Garcinone E)

INCHI for HMDB0033316 (Garcinone E)

Structure for HMDB0033316 (Garcinone E)

3D Structure for HMDB0033316 (Garcinone E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra