MiMeDB: Showing metabocard for all-trans-pentaprenyl diphosphate (MMDBc0033140)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:36:22 UTC

Update Date

2024-04-30 20:01:14 UTC

Metabolite ID

MMDBc0033140

Metabolite Identification

Common Name

all-trans-pentaprenyl diphosphate

Description

all-trans-Pentaprenyl diphosphate (or geranylfarnesyl diphosphate) is a polyprenol. Prenol lipids are synthesized from the 5-carbon precursors isopentenyl diphosphate and dimethylallyl diphosphate that are produced mainly via the mevalonic acid pathway. Simple isoprenoids like Nonadecaprenyl diphosphate are formed by the successive addition of C5 units.[Wikipedia ]

Structure

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


  Mrv0541 02241203512D          

 34 33  0  0  0  0            999 V2000
   23.8058   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8058   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5205   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0971   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3824   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6678   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9531   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9531   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2380   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5233   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8087   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0940   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0940   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3794   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6647   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9560   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2471   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2472   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5325   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8179   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1033   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3886   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3886   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9587   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2441   -8.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5294   -8.1401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.1173   -8.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9422   -7.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8148   -7.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1060   -8.1401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.5182   -8.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6933   -7.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3914   -8.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
M  END

HMDB0012231
     RDKit          3D
Geranylfarnesyl diphosphate
 78 77  0  0  0  0  0  0  0  0999 V2000
   -8.0452    0.6278    3.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606   -0.4923    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8359   -1.8832    3.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8618   -0.2503    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5962    1.1470    1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1789    1.5838    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    0.8229    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -0.6034    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7171    1.4965   -0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374    0.8188   -1.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.9214   -3.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720    0.2335   -3.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112    0.2368   -5.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827   -0.3565   -3.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -1.0481   -4.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.4423   -4.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079   -0.5344   -2.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -1.8750   -2.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.5615   -2.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    0.4287   -0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9005    1.0312   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    0.9053    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    1.5371    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5931    0.2200    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571    0.0953    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635   -1.2194    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.1550    4.0403 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.1680   -2.5201    4.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8437   -0.2807    5.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3682   -0.2783    3.9608 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4468   -0.9654    2.8543 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.6842   -1.4168    3.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9463    0.2113    1.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931   -2.3109    2.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2344    1.2958    3.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5296    0.2279    4.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7727    1.2686    3.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9015   -2.1349    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1604   -2.6000    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6260   -1.9858    4.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5447   -1.0754    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1673    1.8456    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0676    1.3655    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0922    2.6910    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.4723    2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -0.8162    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -1.2039   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.9131    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    2.5500   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    1.2800   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.2691   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5203    1.9523   -3.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    0.3698   -3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    0.8944   -5.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5027   -5.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.7900   -5.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3531   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.1135   -4.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -1.1080   -5.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.5966   -4.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7043   -1.0521   -4.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.0001   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0267   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -2.6714   -3.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027    1.5251   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.6146   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469    1.0035   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571    0.5417   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540    2.1009   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    1.9281    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3832    2.3752    2.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901    0.7444    2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -0.2305   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965    0.6758    2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913    0.5095    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3273    0.3748    5.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3587   -0.1914    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -2.3255    1.1224 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  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 31 34  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
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
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 11 52  1  0
 11 53  1  0
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 21 68  1  0
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 23 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 29 76  1  0
 33 77  1  0
 34 78  1  0
M  END


  Mrv0541 02241203512D          

 34 33  0  0  0  0            999 V2000
   23.8058   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8058   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5205   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0971   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3824   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6678   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9531   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9531   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2380   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5233   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8087   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0940   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0940   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3794   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6647   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9560   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2471   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2472   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5325   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8179   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1033   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3886   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3886   -7.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740   -8.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9587   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2441   -8.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5294   -8.1401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.1173   -8.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9422   -7.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8148   -7.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1060   -8.1401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.5182   -8.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6933   -7.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3914   -8.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 22 24  2  0  0  0  0
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 25 26  1  0  0  0  0
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 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033140

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H44O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,19H,7-10,12,14,16,18,20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17+,25-19+

> <INCHI_KEY>
JMVSBFJBMXQNJW-GIXZANJISA-N

> <FORMULA>
C25H44O7P2

> <MOLECULAR_WEIGHT>
518.5602

> <EXACT_MASS>
518.256226786

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
57.602275585429254

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[hydroxy({[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
6.936161610666666

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1843406094078315

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7672186885241006

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
144.33570000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geranylfarnesyl diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012231
     RDKit          3D
Geranylfarnesyl diphosphate
 78 77  0  0  0  0  0  0  0  0999 V2000
   -8.0452    0.6278    3.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606   -0.4923    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8359   -1.8832    3.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8618   -0.2503    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5962    1.1470    1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1789    1.5838    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    0.8229    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -0.6034    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7171    1.4965   -0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374    0.8188   -1.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.9214   -3.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720    0.2335   -3.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112    0.2368   -5.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827   -0.3565   -3.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -1.0481   -4.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.4423   -4.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079   -0.5344   -2.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -1.8750   -2.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.5615   -2.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    0.4287   -0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9005    1.0312   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    0.9053    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    1.5371    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5931    0.2200    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571    0.0953    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635   -1.2194    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.1550    4.0403 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.1680   -2.5201    4.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8437   -0.2807    5.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3682   -0.2783    3.9608 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4468   -0.9654    2.8543 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.6842   -1.4168    3.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9463    0.2113    1.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931   -2.3109    2.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2344    1.2958    3.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5296    0.2279    4.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7727    1.2686    3.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9015   -2.1349    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1604   -2.6000    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6260   -1.9858    4.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5447   -1.0754    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1673    1.8456    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0676    1.3655    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0922    2.6910    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.4723    2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -0.8162    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -1.2039   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.9131    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    2.5500   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    1.2800   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.2691   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5203    1.9523   -3.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    0.3698   -3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    0.8944   -5.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5027   -5.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.7900   -5.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3531   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.1135   -4.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -1.1080   -5.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.5966   -4.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7043   -1.0521   -4.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.0001   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0267   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -2.6714   -3.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027    1.5251   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.6146   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469    1.0035   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571    0.5417   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540    2.1009   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    1.9281    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3832    2.3752    2.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901    0.7444    2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -0.2305   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965    0.6758    2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913    0.5095    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3273    0.3748    5.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3587   -0.1914    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -2.3255    1.1224 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  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 31 34  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
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 18 62  1  0
 18 63  1  0
 18 64  1  0
 19 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 23 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 29 76  1  0
 33 77  1  0
 34 78  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      44.437 -13.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      44.437 -15.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      45.772 -15.964   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.115 -15.964   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      41.780 -15.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      40.447 -15.964   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.112 -15.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.112 -13.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.778 -15.964   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.443 -15.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.110 -15.964   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.775 -15.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.775 -13.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.442 -15.964   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.107 -15.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.785 -15.964   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.461 -15.195   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.461 -13.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.127 -15.964   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.793 -15.195   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.459 -15.964   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.125 -15.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.125 -13.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.791 -15.964   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.456 -15.195   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      19.122 -15.964   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      17.788 -15.195   0.000  0.00  0.00           P+0
HETATM   28  O   UNK     0      17.019 -16.519   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      18.559 -13.872   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      16.454 -14.436   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      15.131 -15.195   0.000  0.00  0.00           P+0
HETATM   32  O   UNK     0      15.901 -16.519   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.361 -13.872   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      13.797 -15.964   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0012231
HETATM    1  C1  UNL     1      -8.045   0.628   3.594  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.561  -0.492   2.758  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.836  -1.883   3.147  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.862  -0.250   1.633  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.596   1.147   1.260  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.179   1.584   1.294  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.313   0.823   0.382  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.035  -0.603   0.588  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.717   1.496  -0.634  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.837   0.819  -1.593  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.310   0.921  -3.010  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.372   0.234  -3.929  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.711   0.237  -5.391  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.283  -0.357  -3.474  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.338  -1.048  -4.390  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.047  -0.442  -4.330  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.608  -0.534  -2.952  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.783  -1.875  -2.344  1.00  0.00           C  
HETATM   19  C19 UNL     1       1.943   0.561  -2.288  1.00  0.00           C  
HETATM   20  C20 UNL     1       2.496   0.429  -0.923  1.00  0.00           C  
HETATM   21  C21 UNL     1       3.900   1.031  -0.858  1.00  0.00           C  
HETATM   22  C22 UNL     1       4.462   0.905   0.493  1.00  0.00           C  
HETATM   23  C23 UNL     1       3.770   1.537   1.636  1.00  0.00           C  
HETATM   24  C24 UNL     1       5.593   0.220   0.670  1.00  0.00           C  
HETATM   25  C25 UNL     1       6.157   0.095   2.036  1.00  0.00           C  
HETATM   26  O1  UNL     1       6.264  -1.219   2.464  1.00  0.00           O  
HETATM   27  P1  UNL     1       6.925  -1.155   4.040  1.00  0.00           P  
HETATM   28  O2  UNL     1       7.168  -2.520   4.595  1.00  0.00           O  
HETATM   29  O3  UNL     1       5.844  -0.281   5.002  1.00  0.00           O  
HETATM   30  O4  UNL     1       8.368  -0.278   3.961  1.00  0.00           O  
HETATM   31  P2  UNL     1       9.447  -0.965   2.854  1.00  0.00           P  
HETATM   32  O5  UNL     1      10.684  -1.417   3.626  1.00  0.00           O  
HETATM   33  O6  UNL     1       9.946   0.211   1.749  1.00  0.00           O  
HETATM   34  O7  UNL     1       8.793  -2.311   2.101  1.00  0.00           O  
HETATM   35  H1  UNL     1      -7.234   1.296   3.950  1.00  0.00           H  
HETATM   36  H2  UNL     1      -8.530   0.228   4.508  1.00  0.00           H  
HETATM   37  H3  UNL     1      -8.773   1.269   3.040  1.00  0.00           H  
HETATM   38  H4  UNL     1      -8.902  -2.135   2.996  1.00  0.00           H  
HETATM   39  H5  UNL     1      -7.160  -2.600   2.597  1.00  0.00           H  
HETATM   40  H6  UNL     1      -7.626  -1.986   4.232  1.00  0.00           H  
HETATM   41  H7  UNL     1      -6.545  -1.075   1.025  1.00  0.00           H  
HETATM   42  H8  UNL     1      -7.167   1.846   1.935  1.00  0.00           H  
HETATM   43  H9  UNL     1      -7.068   1.366   0.247  1.00  0.00           H  
HETATM   44  H10 UNL     1      -5.092   2.691   1.123  1.00  0.00           H  
HETATM   45  H11 UNL     1      -4.791   1.472   2.363  1.00  0.00           H  
HETATM   46  H12 UNL     1      -2.925  -0.816   0.579  1.00  0.00           H  
HETATM   47  H13 UNL     1      -4.562  -1.204  -0.151  1.00  0.00           H  
HETATM   48  H14 UNL     1      -4.348  -0.913   1.604  1.00  0.00           H  
HETATM   49  H15 UNL     1      -3.928   2.550  -0.691  1.00  0.00           H  
HETATM   50  H16 UNL     1      -1.833   1.280  -1.528  1.00  0.00           H  
HETATM   51  H17 UNL     1      -2.696  -0.269  -1.336  1.00  0.00           H  
HETATM   52  H18 UNL     1      -3.520   1.952  -3.330  1.00  0.00           H  
HETATM   53  H19 UNL     1      -4.291   0.370  -3.117  1.00  0.00           H  
HETATM   54  H20 UNL     1      -3.578   0.894  -5.600  1.00  0.00           H  
HETATM   55  H21 UNL     1      -1.822   0.503  -5.995  1.00  0.00           H  
HETATM   56  H22 UNL     1      -3.008  -0.790  -5.681  1.00  0.00           H  
HETATM   57  H23 UNL     1      -1.041  -0.353  -2.428  1.00  0.00           H  
HETATM   58  H24 UNL     1      -0.231  -2.113  -4.052  1.00  0.00           H  
HETATM   59  H25 UNL     1      -0.707  -1.108  -5.430  1.00  0.00           H  
HETATM   60  H26 UNL     1       1.075   0.597  -4.669  1.00  0.00           H  
HETATM   61  H27 UNL     1       1.704  -1.052  -4.983  1.00  0.00           H  
HETATM   62  H28 UNL     1       1.249  -2.000  -1.388  1.00  0.00           H  
HETATM   63  H29 UNL     1       2.886  -2.027  -2.236  1.00  0.00           H  
HETATM   64  H30 UNL     1       1.440  -2.671  -3.028  1.00  0.00           H  
HETATM   65  H31 UNL     1       1.803   1.525  -2.762  1.00  0.00           H  
HETATM   66  H32 UNL     1       2.498  -0.615  -0.564  1.00  0.00           H  
HETATM   67  H33 UNL     1       1.847   1.004  -0.232  1.00  0.00           H  
HETATM   68  H34 UNL     1       4.557   0.542  -1.612  1.00  0.00           H  
HETATM   69  H35 UNL     1       3.854   2.101  -1.137  1.00  0.00           H  
HETATM   70  H36 UNL     1       2.782   1.928   1.325  1.00  0.00           H  
HETATM   71  H37 UNL     1       4.383   2.375   2.032  1.00  0.00           H  
HETATM   72  H38 UNL     1       3.590   0.744   2.392  1.00  0.00           H  
HETATM   73  H39 UNL     1       6.079  -0.231  -0.175  1.00  0.00           H  
HETATM   74  H40 UNL     1       5.597   0.676   2.773  1.00  0.00           H  
HETATM   75  H41 UNL     1       7.191   0.509   1.990  1.00  0.00           H  
HETATM   76  H42 UNL     1       6.327   0.375   5.581  1.00  0.00           H  
HETATM   77  H43 UNL     1      10.359  -0.191   0.944  1.00  0.00           H  
HETATM   78  H44 UNL     1       8.953  -2.326   1.122  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   44   45
CONECT    7    8    9    9
CONECT    8   46   47   48
CONECT    9   10   49
CONECT   10   11   50   51
CONECT   11   12   52   53
CONECT   12   13   14   14
CONECT   13   54   55   56
CONECT   14   15   57
CONECT   15   16   58   59
CONECT   16   17   60   61
CONECT   17   18   19   19
CONECT   18   62   63   64
CONECT   19   20   65
CONECT   20   21   66   67
CONECT   21   22   68   69
CONECT   22   23   24   24
CONECT   23   70   71   72
CONECT   24   25   73
CONECT   25   26   74   75
CONECT   26   27
CONECT   27   28   28   29   30
CONECT   29   76
CONECT   30   31
CONECT   31   32   32   33   34
CONECT   33   77
CONECT   34   78
END

HMDB0012231
     RDKit          3D
Geranylfarnesyl diphosphate
 78 77  0  0  0  0  0  0  0  0999 V2000
   -8.0452    0.6278    3.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606   -0.4923    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8359   -1.8832    3.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8618   -0.2503    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5962    1.1470    1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1789    1.5838    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    0.8229    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0347   -0.6034    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7171    1.4965   -0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374    0.8188   -1.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.9214   -3.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720    0.2335   -3.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112    0.2368   -5.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827   -0.3565   -3.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -1.0481   -4.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.4423   -4.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079   -0.5344   -2.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -1.8750   -2.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.5615   -2.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    0.4287   -0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9005    1.0312   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    0.9053    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    1.5371    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5931    0.2200    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1571    0.0953    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635   -1.2194    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.1550    4.0403 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.1680   -2.5201    4.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8437   -0.2807    5.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3682   -0.2783    3.9608 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4468   -0.9654    2.8543 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.6842   -1.4168    3.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9463    0.2113    1.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931   -2.3109    2.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2344    1.2958    3.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5296    0.2279    4.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7727    1.2686    3.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9015   -2.1349    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1604   -2.6000    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6260   -1.9858    4.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5447   -1.0754    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1673    1.8456    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0676    1.3655    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0922    2.6910    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.4723    2.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -0.8162    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -1.2039   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.9131    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    2.5500   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    1.2800   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.2691   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5203    1.9523   -3.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    0.3698   -3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    0.8944   -5.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5027   -5.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.7900   -5.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3531   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.1135   -4.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -1.1080   -5.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.5966   -4.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7043   -1.0521   -4.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.0001   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0267   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -2.6714   -3.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027    1.5251   -2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.6146   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469    1.0035   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571    0.5417   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540    2.1009   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    1.9281    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3832    2.3752    2.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901    0.7444    2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -0.2305   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965    0.6758    2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913    0.5095    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3273    0.3748    5.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3587   -0.1914    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -2.3255    1.1224 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  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 31 34  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
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 18 62  1  0
 18 63  1  0
 18 64  1  0
 19 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 23 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 29 76  1  0
 33 77  1  0
 34 78  1  0
M  END

Synonyms

Value	Source
(2E,6E,10E,14E)-Geranylfarnesyl diphosphate	ChEBI
2-trans,6-trans,10-trans,14-trans-Geranylfarnesyl diphosphate	ChEBI
all-trans-Farnesylgeranyl diphosphate	ChEBI
all-trans-Farnesylgeranyl pyrophosphate	ChEBI
all-trans-Geranylfarnesyl diphosphate	ChEBI
all-trans-Geranylfarnesyl pyrophosphate	ChEBI
(2E,6E,10E,14E)-Geranylfarnesyl diphosphoric acid	Generator
2-trans,6-trans,10-trans,14-trans-Geranylfarnesyl diphosphoric acid	Generator
all-trans-Farnesylgeranyl diphosphoric acid	Generator
all-trans-Farnesylgeranyl pyrophosphoric acid	Generator
all-trans-Geranylfarnesyl diphosphoric acid	Generator
all-trans-Geranylfarnesyl pyrophosphoric acid	Generator
Geranylfarnesyl diphosphoric acid	Generator
all-trans-Pentaprenyl diphosphate	HMDB
Geranylfarnesyl-diphosphate	HMDB
Geranylfarnesyl-PP	HMDB
GFPP	HMDB
Geranylfarnesyl diphosphate	ChEBI
all-trans-Pentaprenyl diphosphoric acid	Generator

Molecular Formula

C₂₅H₄₄O₇P₂

Average Mass

518.5602

Monoisotopic Mass

518.256226786

IUPAC Name

{[hydroxy({[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional Name

geranylfarnesyl diphosphate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI Identifier

InChI=1S/C25H44O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,19H,7-10,12,14,16,18,20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17+,25-19+

InChI Key

JMVSBFJBMXQNJW-GIXZANJISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyprenyl diphosphates. These are prenol lipids in which the diphosphate group is linked to one end of the polyprenol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenyl diphosphates

Alternative Parents

Substituents

Polyprenyl diphosphate
Polyprenyl monophosphate
Sesterterpenoid
Organic pyrophosphate
Isoprenoid phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pentaprenyl diphosphate (CHEBI:16818 )
Acyclic sesterterpenoids (C04217 )
Polyterpenoids (C04217 )
Acyclic sesterterpenoids (LMPR0105010014 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	4.88	ALOGPS
logP	6.94	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	144.34 m³·mol⁻¹	ChemAxon
Polarizability	57.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fvj-8897540000-8727b5480b3179b9518e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0frl-1319560000-894aa5718fd0aa23d1a4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-3429200000-52610beb1a44f351baba	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0i0c-4349100000-efc21b59b7ba7930287d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0400190000-b7d52827f6b8fc1b2470	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-7900100000-cf42494f155a7efd500e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-3b304fd455493d238af5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-befd6f91805f0ef51f2d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2400290000-e7717fe9142147d4137b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9400000000-cd37df82a8f7acbc7eda	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0203490000-a68127df024e6760e7ef	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002n-1119400000-33d1f9d47cff2aaf5fce	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01yt-2935000000-244031b6c35d30ad5dce	2021-09-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007426	2-trans,6-trans,10-trans-Geranylgeranyl diphosphate	all-trans-pentaprenyl diphosphate	Not Available		VMH	30371894
MMDBr0007541	Isopentenyl pyrophosphate	all-trans-Hexaprenyl diphosphate	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	12	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	326	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Proteobacteria	117	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	64	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	37	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1
Archaea/Archaea	Euryarchaeota	2		Metabolic reconstruction
Viruses/Bamfordvirae	Nucleocytoviricota	5

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012231

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028874

KNApSAcK ID

Not Available

Chemspider ID

4444258

KEGG Compound ID

C04217

BioCyc ID

ALL-TRANS-PENTAPRENYL-DIPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Geranylfarnesyl pyrophosphate

METLIN ID

Not Available

PubChem Compound

5280659

PDB ID

Not Available

ChEBI ID

16818

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for all-trans-pentaprenyl diphosphate (MMDBc0033140)

MOL for #<Metabolite:0x00007fdb09295630>

3D MOL for #<Metabolite:0x00007fdb09295630>

3D SDF for #<Metabolite:0x00007fdb09295630>

3D-SDF for #<Metabolite:0x00007fdb09295630>

PDB for #<Metabolite:0x00007fdb09295630>

3D PDB for #<Metabolite:0x00007fdb09295630>

SMILES for #<Metabolite:0x00007fdb09295630>

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Structure for #<Metabolite:0x00007fdb09295630>

3D Structure for #<Metabolite:0x00007fdb09295630>