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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:41:29 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035683

Secondary Accession Numbers

HMDB35683

Metabolite Identification

Common Name

Dukunolide A

Description

Dukunolide A belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Dukunolide A has been detected, but not quantified in, fruits. This could make dukunolide a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dukunolide A.

Structure

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

  Mrv0541 05061308382D          

 35 41  0  0  0  0            999 V2000
    2.1435   -1.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -1.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -4.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5788   -2.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9219   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0577   -4.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4752   -3.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283   -5.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612   -2.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678   -4.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0575   -3.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6108   -4.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447   -3.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1932   -4.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829   -4.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0866   -1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260   -1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7145   -3.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793   -3.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436   -2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399   -2.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -2.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4326   -4.6058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -4.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903   -0.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8473   -1.3319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -3.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0293   -6.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502   -4.7853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077   -4.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 12  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 20  1  0  0  0  0
 22  3  1  0  0  0  0
 22  8  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
 23  4  1  0  0  0  0
 24 10  1  0  0  0  0
 24 20  1  0  0  0  0
 25 15  1  0  0  0  0
 25 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 17  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  2  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32  9  1  0  0  0  0
 32 11  1  0  0  0  0
 33 16  1  0  0  0  0
 33 18  1  0  0  0  0
 34 17  1  0  0  0  0
 34 26  1  0  0  0  0
 35 19  1  0  0  0  0
 35 23  1  0  0  0  0
M  END

HMDB0035683
     RDKit          3D
Dukunolide A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.6462    0.8400   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313   -0.4115   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -1.5881   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.6918   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494   -1.7991   -2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095   -1.3068   -1.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -1.4676   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -1.4915    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -2.5913    1.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.4510    0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -2.3954    1.2109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -0.2661    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0970    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5575   -0.5840   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943    1.0099    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7432    2.2238    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805    2.0160   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    2.3607   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    3.4074   -1.8356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    1.3539   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593    0.9926    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    2.1682    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -0.2285    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646   -0.3259    2.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.2564    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.6357   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.1480    2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    0.5223    3.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    0.1277    2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407   -0.3723    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    0.3628    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.7353    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0495    1.9421    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6004    0.7961    0.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.1769    0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049    0.9571   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    1.6991   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    0.7894   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.5404   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -1.4124   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -0.9115   -3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -2.6726   -2.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -2.2818   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -2.4455   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -0.6919   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.0870    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.6035    1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6382   -0.5762    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    0.9748    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629   -0.4250   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -1.6798   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.0486   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    1.9639   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2235    2.3427    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9023    3.0342    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.9451    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.0686    2.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548   -1.4283    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523    2.4375    0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729    2.9579    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9822   -1.2355    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 26  2  1  0
 35 31  2  0
 30  2  1  0
 26  6  1  0
 23  8  1  0
 17 15  1  0
 21 15  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  7 44  1  0
  7 45  1  0
  9 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 17 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 30 58  1  0
 32 59  1  0
 33 60  1  0
 35 61  1  0
M  END

  Mrv0541 05061308382D          

 35 41  0  0  0  0            999 V2000
    2.1435   -1.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -1.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -4.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5788   -2.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9219   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0577   -4.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4752   -3.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5283   -5.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503   -5.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612   -2.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678   -4.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0575   -3.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6108   -4.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447   -3.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1932   -4.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829   -4.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0866   -1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260   -1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7145   -3.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793   -3.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436   -2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399   -2.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -2.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4326   -4.6058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -4.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903   -0.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8473   -1.3319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -3.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0293   -6.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502   -4.7853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077   -4.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 12  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 20  1  0  0  0  0
 22  3  1  0  0  0  0
 22  8  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
 23  4  1  0  0  0  0
 24 10  1  0  0  0  0
 24 20  1  0  0  0  0
 25 15  1  0  0  0  0
 25 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 17  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  2  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32  9  1  0  0  0  0
 32 11  1  0  0  0  0
 33 16  1  0  0  0  0
 33 18  1  0  0  0  0
 34 17  1  0  0  0  0
 34 26  1  0  0  0  0
 35 19  1  0  0  0  0
 35 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035683

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O9/c1-21(2)20(29)24(30)10-12-6-5-8-22(3)14(12)15(18(27)33-16(22)13-7-9-32-11-13)25(24,31)23(4)26(21)17(34-26)19(28)35-23/h6-7,9,11,16-17,30-31H,5,8,10H2,1-4H3

> <INCHI_KEY>
BATTZJIKLZSIAU-UHFFFAOYSA-N

> <FORMULA>
C26H26O9

> <MOLECULAR_WEIGHT>
482.4792

> <EXACT_MASS>
482.15768243

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
47.53870209998039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.8801818813333333

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.689707105267313

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.330872021483968

> <JCHEM_PKA_STRONGEST_BASIC>
-3.161934552614969

> <JCHEM_POLAR_SURFACE_AREA>
135.8

> <JCHEM_REFRACTIVITY>
117.13519999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035683
     RDKit          3D
Dukunolide A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.6462    0.8400   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313   -0.4115   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -1.5881   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.6918   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494   -1.7991   -2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095   -1.3068   -1.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -1.4676   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -1.4915    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -2.5913    1.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.4510    0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -2.3954    1.2109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -0.2661    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0970    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5575   -0.5840   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943    1.0099    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7432    2.2238    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805    2.0160   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    2.3607   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    3.4074   -1.8356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    1.3539   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593    0.9926    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    2.1682    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -0.2285    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646   -0.3259    2.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.2564    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.6357   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.1480    2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    0.5223    3.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    0.1277    2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407   -0.3723    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    0.3628    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.7353    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0495    1.9421    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6004    0.7961    0.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.1769    0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049    0.9571   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    1.6991   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    0.7894   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.5404   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -1.4124   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -0.9115   -3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -2.6726   -2.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -2.2818   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -2.4455   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -0.6919   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.0870    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.6035    1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6382   -0.5762    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    0.9748    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629   -0.4250   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -1.6798   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.0486   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    1.9639   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2235    2.3427    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9023    3.0342    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.9451    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.0686    2.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548   -1.4283    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523    2.4375    0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729    2.9579    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9822   -1.2355    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 26  2  1  0
 35 31  2  0
 30  2  1  0
 26  6  1  0
 23  8  1  0
 17 15  1  0
 21 15  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  7 44  1  0
  7 45  1  0
  9 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 17 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 30 58  1  0
 32 59  1  0
 33 60  1  0
 35 61  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  -2.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.024  -3.698   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.893  -7.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.837  -7.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.280  -4.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.054  -3.753   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.174  -8.823   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.087  -6.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.053 -10.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.408  -3.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.667 -10.807   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.634  -4.349   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.700  -9.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.441  -5.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.021  -6.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.473  -8.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.883  -6.085   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.827  -8.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.328  -7.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.762  -3.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.342  -3.679   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.667  -6.808   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.375  -6.138   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.988  -4.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.794  -5.542   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.148  -5.207   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.408  -8.597   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.397  -8.786   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.955  -1.555   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.182  -2.486   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.643  -6.890   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.121 -11.314   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.054  -8.933   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.755  -4.551   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.868  -7.592   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5    6    8                                                       
CONECT    6    5   12                                                       
CONECT    7    9   13                                                       
CONECT    8    5   22                                                       
CONECT    9    7   32                                                       
CONECT   10   12   24                                                       
CONECT   11   13   32                                                       
CONECT   12    6   10   14                                                  
CONECT   13    7   11   16                                                  
CONECT   14   12   15   22                                                  
CONECT   15   14   18   25                                                  
CONECT   16   13   22   33                                                  
CONECT   17   19   26   34                                                  
CONECT   18   15   27   33                                                  
CONECT   19   17   28   35                                                  
CONECT   20   21   24   29                                                  
CONECT   21    1    2   20   26                                             
CONECT   22    3    8   14   16                                             
CONECT   23    4   25   26   35                                             
CONECT   24   10   20   25   30                                             
CONECT   25   15   23   24   31                                             
CONECT   26   17   21   23   34                                             
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32    9   11                                                       
CONECT   33   16   18                                                       
CONECT   34   17   26                                                       
CONECT   35   19   23                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

COMPND    HMDB0035683
HETATM    1  C1  UNL     1       2.646   0.840  -1.170  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.431  -0.411  -0.367  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.947  -1.588  -1.164  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.220  -1.692  -2.487  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.749  -1.799  -2.247  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.209  -1.307  -1.145  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.272  -1.468  -1.003  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.607  -1.492   0.455  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.036  -2.591   1.087  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.080  -1.451   0.698  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.631  -2.395   1.211  1.00  0.00           O  
HETATM   12  C10 UNL     1      -3.847  -0.266   0.313  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.962  -0.097   1.357  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.558  -0.584  -1.000  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.094   1.010   0.278  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.743   2.224   0.493  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.281   2.016  -0.781  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.902   2.361  -1.174  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.580   3.407  -1.836  1.00  0.00           O  
HETATM   20  O5  UNL     1      -1.076   1.354  -0.693  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.659   0.993   0.566  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.312   2.168   1.490  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.077  -0.229   1.149  1.00  0.00           C  
HETATM   24  O6  UNL     1      -1.465  -0.326   2.483  1.00  0.00           O  
HETATM   25  C19 UNL     1       0.399  -0.256   1.012  1.00  0.00           C  
HETATM   26  C20 UNL     1       0.991  -0.636  -0.105  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.217   0.148   2.139  1.00  0.00           C  
HETATM   28  O7  UNL     1       0.667   0.522   3.243  1.00  0.00           O  
HETATM   29  O8  UNL     1       2.590   0.128   2.016  1.00  0.00           O  
HETATM   30  C22 UNL     1       3.241  -0.372   0.903  1.00  0.00           C  
HETATM   31  C23 UNL     1       4.507   0.363   0.655  1.00  0.00           C  
HETATM   32  C24 UNL     1       4.721   1.735   0.707  1.00  0.00           C  
HETATM   33  C25 UNL     1       6.050   1.942   0.401  1.00  0.00           C  
HETATM   34  O9  UNL     1       6.600   0.796   0.182  1.00  0.00           O  
HETATM   35  C26 UNL     1       5.736  -0.177   0.317  1.00  0.00           C  
HETATM   36  H1  UNL     1       3.705   0.957  -1.394  1.00  0.00           H  
HETATM   37  H2  UNL     1       2.267   1.699  -0.582  1.00  0.00           H  
HETATM   38  H3  UNL     1       2.111   0.789  -2.143  1.00  0.00           H  
HETATM   39  H4  UNL     1       2.905  -2.540  -0.606  1.00  0.00           H  
HETATM   40  H5  UNL     1       4.015  -1.412  -1.403  1.00  0.00           H  
HETATM   41  H6  UNL     1       2.502  -0.912  -3.190  1.00  0.00           H  
HETATM   42  H7  UNL     1       2.528  -2.673  -2.939  1.00  0.00           H  
HETATM   43  H8  UNL     1       0.140  -2.282  -2.985  1.00  0.00           H  
HETATM   44  H9  UNL     1      -1.606  -2.445  -1.430  1.00  0.00           H  
HETATM   45  H10 UNL     1      -1.841  -0.692  -1.512  1.00  0.00           H  
HETATM   46  H11 UNL     1      -0.412  -3.087   0.513  1.00  0.00           H  
HETATM   47  H12 UNL     1      -5.884  -0.604   1.024  1.00  0.00           H  
HETATM   48  H13 UNL     1      -4.638  -0.576   2.300  1.00  0.00           H  
HETATM   49  H14 UNL     1      -5.124   0.975   1.595  1.00  0.00           H  
HETATM   50  H15 UNL     1      -5.663  -0.425  -0.927  1.00  0.00           H  
HETATM   51  H16 UNL     1      -4.459  -1.680  -1.257  1.00  0.00           H  
HETATM   52  H17 UNL     1      -4.122  -0.049  -1.858  1.00  0.00           H  
HETATM   53  H18 UNL     1      -4.074   1.964  -1.547  1.00  0.00           H  
HETATM   54  H19 UNL     1      -0.223   2.343   1.396  1.00  0.00           H  
HETATM   55  H20 UNL     1      -1.902   3.034   1.097  1.00  0.00           H  
HETATM   56  H21 UNL     1      -1.570   1.945   2.544  1.00  0.00           H  
HETATM   57  H22 UNL     1      -2.357   0.069   2.654  1.00  0.00           H  
HETATM   58  H23 UNL     1       3.555  -1.428   1.167  1.00  0.00           H  
HETATM   59  H24 UNL     1       3.952   2.437   0.947  1.00  0.00           H  
HETATM   60  H25 UNL     1       6.473   2.958   0.376  1.00  0.00           H  
HETATM   61  H26 UNL     1       5.982  -1.235   0.177  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   26   30
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6    6   43
CONECT    6    7   26
CONECT    7    8   44   45
CONECT    8    9   10   23
CONECT    9   46
CONECT   10   11   11   12
CONECT   12   13   14   15
CONECT   13   47   48   49
CONECT   14   50   51   52
CONECT   15   16   17   21
CONECT   16   17
CONECT   17   18   53
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   23
CONECT   22   54   55   56
CONECT   23   24   25
CONECT   24   57
CONECT   25   26   26   27
CONECT   27   28   28   29
CONECT   29   30
CONECT   30   31   58
CONECT   31   32   35   35
CONECT   32   33   33   59
CONECT   33   34   60
CONECT   34   35
CONECT   35   61
END

HMDB0035683
     RDKit          3D
Dukunolide A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.6462    0.8400   -1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313   -0.4115   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -1.5881   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.6918   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494   -1.7991   -2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095   -1.3068   -1.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -1.4676   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -1.4915    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -2.5913    1.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.4510    0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -2.3954    1.2109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -0.2661    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -0.0970    1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5575   -0.5840   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943    1.0099    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7432    2.2238    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805    2.0160   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    2.3607   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    3.4074   -1.8356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    1.3539   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593    0.9926    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    2.1682    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -0.2285    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646   -0.3259    2.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.2564    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.6357   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.1480    2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    0.5223    3.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    0.1277    2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407   -0.3723    0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    0.3628    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    1.7353    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0495    1.9421    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6004    0.7961    0.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.1769    0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049    0.9571   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    1.6991   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    0.7894   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.5404   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -1.4124   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -0.9115   -3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -2.6726   -2.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -2.2818   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -2.4455   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412   -0.6919   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.0870    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841   -0.6035    1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6382   -0.5762    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    0.9748    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629   -0.4250   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -1.6798   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.0486   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    1.9639   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2235    2.3427    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9023    3.0342    1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.9451    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.0686    2.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548   -1.4283    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523    2.4375    0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729    2.9579    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9822   -1.2355    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 26  2  1  0
 35 31  2  0
 30  2  1  0
 26  6  1  0
 23  8  1  0
 17 15  1  0
 21 15  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  7 44  1  0
  7 45  1  0
  9 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 17 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 30 58  1  0
 32 59  1  0
 33 60  1  0
 35 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,1,1-trifluoro-2-Octanol	HMDB
1,1,1-Trifluorooctan-2-ol	HMDB

Chemical Formula

C₂₆H₂₆O₉

Average Molecular Weight

482.4792

Monoisotopic Molecular Weight

482.15768243

IUPAC Name

18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione

Traditional Name

18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione

CAS Registry Number

97804-04-1

SMILES

CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1

InChI Identifier

InChI=1S/C26H26O9/c1-21(2)20(29)24(30)10-12-6-5-8-22(3)14(12)15(18(27)33-16(22)13-7-9-32-11-13)25(24,31)23(4)26(21)17(34-26)19(28)35-23/h6-7,9,11,16-17,30-31H,5,8,10H2,1-4H3

InChI Key

BATTZJIKLZSIAU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthofuran
Naphthalene
Dihydropyranone
Para-dioxane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Ketone
1,2-diol
Lactone
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035683)

Source

Endogenous

Endogenous (HMDB: HMDB0035683)

Plant

Plant (HMDB: HMDB0035683)

Exogenous

Food

Food (HMDB: HMDB0035683)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035683)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035683)

Role

Biological role

Energy source (HMDB: HMDB0035683)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035683)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	279 - 281 °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	0.28 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.88	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.14 m³·mol⁻¹	ChemAxon
Polarizability	47.54 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	206.758	31661259
DarkChem	[M-H]-	192.825	31661259
DeepCCS	[M-2H]-	244.731	30932474
DeepCCS	[M+Na]+	220.222	30932474
AllCCS	[M+H]+	208.2	32859911
AllCCS	[M+H-H2O]+	206.2	32859911
AllCCS	[M+NH4]+	210.0	32859911
AllCCS	[M+Na]+	210.5	32859911
AllCCS	[M-H]-	215.9	32859911
AllCCS	[M+Na-2H]-	216.6	32859911
AllCCS	[M+HCOO]-	217.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dukunolide A	CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1	4973.7	Standard polar	33892256
Dukunolide A	CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1	3176.0	Standard non polar	33892256
Dukunolide A	CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1	3852.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dukunolide A,1TMS,isomer #1	CC12CCC=C3CC4(O[Si](C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O)C(=C31)C(=O)OC2C1=COC=C1	3626.0	Semi standard non polar	33892256
Dukunolide A,1TMS,isomer #2	CC12CCC=C3CC4(O)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C)C(=C31)C(=O)OC2C1=COC=C1	3633.9	Semi standard non polar	33892256
Dukunolide A,2TMS,isomer #1	CC12CCC=C3CC4(O[Si](C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C)C(=C31)C(=O)OC2C1=COC=C1	3594.6	Semi standard non polar	33892256
Dukunolide A,1TBDMS,isomer #1	CC12CCC=C3CC4(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O)C(=C31)C(=O)OC2C1=COC=C1	3875.7	Semi standard non polar	33892256
Dukunolide A,1TBDMS,isomer #2	CC12CCC=C3CC4(O)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C(C)(C)C)C(=C31)C(=O)OC2C1=COC=C1	3882.4	Semi standard non polar	33892256
Dukunolide A,2TBDMS,isomer #1	CC12CCC=C3CC4(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C(C)(C)C)C(=C31)C(=O)OC2C1=COC=C1	4094.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6w-9187700000-0c2a7c908194de1bc5f3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (2 TMS) - 70eV, Positive	splash10-002f-9500682000-d4a39e6552e42584c571	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dukunolide A GC-MS ("Dukunolide A,1TMS,#2" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - Dukunolide A 10V, Positive-QTOF	splash10-001i-0000900000-da8ac3e0960d9da6301a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 20V, Positive-QTOF	splash10-00lr-1001900000-a7a4ec4957242dee0a6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 40V, Positive-QTOF	splash10-0002-7709200000-399347021ab16db3424a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 10V, Negative-QTOF	splash10-001r-0000900000-bd77068acce7dc5d8ed7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 20V, Negative-QTOF	splash10-01qi-1100900000-713c9a5813e43e4afe8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 40V, Negative-QTOF	splash10-0aos-9806800000-317daa3f79d0b756a9b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 10V, Negative-QTOF	splash10-001i-0000900000-e224776f4657f4af7bc6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 20V, Negative-QTOF	splash10-001i-2001900000-7d43705e485ecb09784a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 40V, Negative-QTOF	splash10-000i-2034900000-d50d05351d98039d86e2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 10V, Positive-QTOF	splash10-001i-0000900000-0b0163d042220f372611	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 20V, Positive-QTOF	splash10-001i-1009800000-7a79187b060f7832fe21	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dukunolide A 40V, Positive-QTOF	splash10-000y-2590500000-7d4e6f2c065482024976	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014400

KNApSAcK ID

Not Available

Chemspider ID

35013993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73820465

PDB ID

Not Available

ChEBI ID

172707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1850891

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 Dukunolide A (HMDB0035683)

MOL for HMDB0035683 (Dukunolide A)

3D MOL for HMDB0035683 (Dukunolide A)

3D SDF for HMDB0035683 (Dukunolide A)

3D-SDF for HMDB0035683 (Dukunolide A)

PDB for HMDB0035683 (Dukunolide A)

3D PDB for HMDB0035683 (Dukunolide A)

SMILES for HMDB0035683 (Dukunolide A)

INCHI for HMDB0035683 (Dukunolide A)

Structure for HMDB0035683 (Dukunolide A)

3D Structure for HMDB0035683 (Dukunolide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra