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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:20:42 UTC

Update Date

2022-03-07 02:51:22 UTC

HMDB ID

HMDB0012188

Secondary Accession Numbers

HMDB12188

Metabolite Identification

Common Name

all-trans-Hexaprenyl diphosphate

Description

all-trans-Hexaprenyl diphosphate is the final product of the hexaprenyl diphosphate biosynthesis pathway. In this pathway, multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form various polyisoprenoids. There are two different pathways for the biosynthesis of IPP. Bacteria that possess ubiquinone generally use the methylerythritol phosphate pathway (MEP), while the eukaryotic microorganisms use the mevalonate pathway. However, exceptions exist. For example, some eukaryotic microbes, like the green algae and the malarial parasite Plasmodium falciparum, appear to utilize the MEP pathway, and some bacteria utilize the mevalonate pathway (Eisenreich01, Eisenreich04). In Saccharomyces cerevisiae S288C, the initial addition of two isoprenyl units to form (E, E)-farnesyl diphosphate is catalyzed by geranyltransferase / dimethylallyltransferase, encoded by FPP1. An additional unit is added by farnesyltranstransferase (encoded by BTS1), resulting in the formation of all-trans-geranyl-geranyl diphosphate. The last enzyme in this pathway is hexaprenyl diphosphate synthase (encoded by COQ1), which adds additional isoprenoid units to a maximal length unique to the organism. In the case of Saccharomyces cerevisiae S288C, it is 6 units. Polyprenyl diphosphate synthase enzymes, such as hexaprenyl diphosphate synthase, are responsible for determining the final length of the tail. When yeast COQ1 mutants are complemented with homologs from other organisms, ubiquinone biosynthesis is restored, but the tail length of the quinone depends on the source of the enzyme.

Structure

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


  Mrv1652309042000342D          

 39 38  0  0  0  0            999 V2000
   13.9485   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6630   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3775   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6630   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0919   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8065   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5209   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2353   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5209   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9499   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6642   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0933   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8078   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0906   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8051   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5196   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8051   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2340   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2327   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9472   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6616   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9472   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3760   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3747   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8038   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5182   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5223   -8.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2372   -8.0932    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.9519   -8.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8233   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6488   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6668   -8.0932    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.2531   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3857   -8.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0784   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
  1 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 16 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  2  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 21 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 32 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 31 15  1  0  0  0  0
M  END

HMDB0012188
     RDKit          3D
all-trans-Hexaprenyl diphosphate
 91 90  0  0  0  0  0  0  0  0999 V2000
  -12.6649   -0.8560   -2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5704    0.1360   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5447    1.3306   -2.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6382   -0.0718   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.8363   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1492    0.2928   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596   -0.8627   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   -2.1911   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7134   -0.7720    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2733   -1.8816    1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8469   -2.3070    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950   -1.1841    1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831   -0.5412    2.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -0.6989    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643    0.4262    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -0.1070    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    1.0449    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2548    1.7137    2.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143    1.4709   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    2.5788   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    2.2430   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    1.2542    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.0943    0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9249    1.5908    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997    0.7234    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0657    0.7785    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512    0.3704    0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2702    0.5028    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2224   -0.0987   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9366   -0.5105   -1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2896   -0.3846   -1.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0481   -0.8643   -2.8039 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1606   -0.4769   -3.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2490   -2.5418   -2.8713 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -0.0468   -2.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4769   -0.2337   -1.5810 P   0  0  0  0  0  5  0  0  0  0  0  0
   12.1323   -1.5198   -0.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2476    1.0265   -0.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1090   -0.2036   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3748   -1.5314   -2.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8302   -1.4509   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6206   -0.3399   -2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5328    1.4407   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7787    1.2616   -3.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4121    2.2587   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7457   -0.9644   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6118    1.2209    0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    1.7259   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    1.1347   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9667   -0.0008   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6049   -2.9386   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9671   -2.2708   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1123   -2.3849    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1990    0.1924    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120   -2.7590    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2412   -1.5011    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016   -2.6587    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268   -3.1305    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1852    0.4874    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -0.5906    3.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -1.1049    3.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -1.1274   -0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.7986    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    1.2550    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.4553   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4943   -0.8948    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.6559    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    1.7680    2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    1.0154    2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294    0.9622   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    3.3024   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    3.1824    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690    3.1901   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045    1.7899   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6883   -0.0893    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.2726   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0535   -0.8839    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2923    2.6227    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    1.1075    3.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848   -0.3146    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4814    0.1606    2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3981    1.8302    2.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5262    1.2409    0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    0.8925    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7469   -0.4745    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -0.1956   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -1.5926   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554    0.0314   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5754   -2.7625   -3.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1198    1.3551   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5674   -0.9708   -1.6258 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  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  6 50  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 18 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 23 75  1  0
 23 76  1  0
 23 77  1  0
 24 78  1  0
 25 79  1  0
 25 80  1  0
 26 81  1  0
 26 82  1  0
 28 83  1  0
 28 84  1  0
 28 85  1  0
 29 86  1  0
 30 87  1  0
 30 88  1  0
 34 89  1  0
 38 90  1  0
 39 91  1  0
M  END


  Mrv1652309042000342D          

 39 38  0  0  0  0            999 V2000
   13.9485   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6630   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3775   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6630   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0919   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8065   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5209   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2353   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5209   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9499   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6642   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0933   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8078   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0906   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8051   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5196   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8051   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2340   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2327   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9472   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6616   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9472   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3760   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3747   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8038   -8.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0892   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5182   -8.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5223   -8.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2372   -8.0932    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.9519   -8.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8233   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6488   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6668   -8.0932    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.2531   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3857   -8.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0784   -7.3780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
  1 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 16 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  2  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 21 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 32 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 31 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012188

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CC\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/C30H52O7P2/c1-25(2)13-8-14-26(3)15-9-16-27(4)17-10-18-28(5)19-11-20-29(6)21-12-22-30(7)23-24-36-39(34,35)37-38(31,32)33/h13,15,17,19,21,23H,8-12,14,16,18,20,22,24H2,1-7H3,(H,34,35)(H2,31,32,33)/b26-15+,27-17+,28-19+,29-21+,30-23+

> <INCHI_KEY>
NGFSMHKFTZROKJ-MMSZMYIBSA-N

> <FORMULA>
C30H52O7P2

> <MOLECULAR_WEIGHT>
586.6772

> <EXACT_MASS>
586.318827042

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
67.36499667038598

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

> <ALOGPS_LOGP>
5.95

> <JCHEM_LOGP>
8.595875885666667

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2043406094078315

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7672186885241006

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
168.13830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012188
     RDKit          3D
all-trans-Hexaprenyl diphosphate
 91 90  0  0  0  0  0  0  0  0999 V2000
  -12.6649   -0.8560   -2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5704    0.1360   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5447    1.3306   -2.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6382   -0.0718   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.8363   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1492    0.2928   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596   -0.8627   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   -2.1911   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7134   -0.7720    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2733   -1.8816    1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8469   -2.3070    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950   -1.1841    1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831   -0.5412    2.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -0.6989    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643    0.4262    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -0.1070    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    1.0449    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2548    1.7137    2.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143    1.4709   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    2.5788   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    2.2430   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    1.2542    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.0943    0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9249    1.5908    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997    0.7234    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0657    0.7785    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512    0.3704    0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2702    0.5028    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2224   -0.0987   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9366   -0.5105   -1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2896   -0.3846   -1.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0481   -0.8643   -2.8039 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1606   -0.4769   -3.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2490   -2.5418   -2.8713 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -0.0468   -2.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4769   -0.2337   -1.5810 P   0  0  0  0  0  5  0  0  0  0  0  0
   12.1323   -1.5198   -0.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2476    1.0265   -0.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1090   -0.2036   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3748   -1.5314   -2.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8302   -1.4509   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6206   -0.3399   -2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5328    1.4407   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7787    1.2616   -3.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4121    2.2587   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7457   -0.9644   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6118    1.2209    0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    1.7259   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    1.1347   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9667   -0.0008   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6049   -2.9386   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9671   -2.2708   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1123   -2.3849    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1990    0.1924    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120   -2.7590    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2412   -1.5011    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016   -2.6587    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268   -3.1305    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1852    0.4874    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -0.5906    3.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -1.1049    3.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -1.1274   -0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.7986    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    1.2550    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.4553   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4943   -0.8948    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.6559    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    1.7680    2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    1.0154    2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294    0.9622   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    3.3024   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    3.1824    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690    3.1901   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045    1.7899   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6883   -0.0893    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.2726   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0535   -0.8839    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2923    2.6227    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    1.1075    3.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848   -0.3146    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4814    0.1606    2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3981    1.8302    2.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5262    1.2409    0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    0.8925    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7469   -0.4745    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -0.1956   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -1.5926   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554    0.0314   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5754   -2.7625   -3.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1198    1.3551   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5674   -0.9708   -1.6258 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  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  6 50  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 18 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 23 75  1  0
 23 76  1  0
 23 77  1  0
 24 78  1  0
 25 79  1  0
 25 80  1  0
 26 81  1  0
 26 82  1  0
 28 83  1  0
 28 84  1  0
 28 85  1  0
 29 86  1  0
 30 87  1  0
 30 88  1  0
 34 89  1  0
 38 90  1  0
 39 91  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      26.037 -15.876   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.371 -15.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.705 -15.876   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.371 -13.566   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.038 -15.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.372 -15.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.706 -15.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.039 -15.876   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.706 -13.566   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.373 -15.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.707 -15.876   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.040 -15.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.374 -15.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.040 -13.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.708 -15.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.702 -15.876   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.036 -15.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.370 -15.876   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.036 -13.566   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.703 -15.106   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.368 -15.876   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.701 -15.106   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.035 -15.876   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.701 -13.566   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.369 -15.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.033 -15.876   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.367 -15.106   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.700 -15.876   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.367 -13.566   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.034 -15.106   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      42.042 -15.876   0.000  0.00  0.00           O+0
HETATM   32  P   UNK     0      43.376 -15.107   0.000  0.00  0.00           P+0
HETATM   33  O   UNK     0      44.710 -15.876   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      42.603 -13.772   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      44.144 -13.772   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      46.045 -15.107   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      45.272 -13.772   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      47.387 -15.880   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      46.813 -13.772   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5                                                       
CONECT    4    2                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   31                                                       
CONECT   16   17   25                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18    1                                                       
CONECT   21   22   30                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   16                                                       
CONECT   26   27                                                            
CONECT   27   26   28   29                                                  
CONECT   28   27   30                                                       
CONECT   29   27                                                            
CONECT   30   28   21                                                       
CONECT   31   32   15                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32   36                                                       
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   33   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   76    0
END

COMPND    HMDB0012188
HETATM    1  C1  UNL     1     -12.665  -0.856  -2.055  1.00  0.00           C  
HETATM    2  C2  UNL     1     -11.570   0.136  -1.914  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.545   1.331  -2.806  1.00  0.00           C  
HETATM    4  C4  UNL     1     -10.638  -0.072  -0.986  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.511   0.836  -0.754  1.00  0.00           C  
HETATM    6  C6  UNL     1      -8.149   0.293  -0.970  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.760  -0.863  -0.146  1.00  0.00           C  
HETATM    8  C8  UNL     1      -8.428  -2.191  -0.189  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.713  -0.772   0.705  1.00  0.00           C  
HETATM   10  C10 UNL     1      -6.273  -1.882   1.554  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.847  -2.307   1.269  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.895  -1.184   1.495  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.783  -0.541   2.848  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.112  -0.699   0.547  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.164   0.426   0.790  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.761  -0.107   0.507  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.162   1.045   0.760  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.255   1.714   2.070  1.00  0.00           C  
HETATM   19  C19 UNL     1       0.914   1.471  -0.226  1.00  0.00           C  
HETATM   20  C20 UNL     1       1.866   2.579  -0.152  1.00  0.00           C  
HETATM   21  C21 UNL     1       3.296   2.243  -0.419  1.00  0.00           C  
HETATM   22  C22 UNL     1       3.886   1.254   0.534  1.00  0.00           C  
HETATM   23  C23 UNL     1       3.302  -0.094   0.660  1.00  0.00           C  
HETATM   24  C24 UNL     1       4.925   1.591   1.283  1.00  0.00           C  
HETATM   25  C25 UNL     1       5.600   0.723   2.252  1.00  0.00           C  
HETATM   26  C26 UNL     1       7.066   0.778   2.139  1.00  0.00           C  
HETATM   27  C27 UNL     1       7.751   0.370   0.922  1.00  0.00           C  
HETATM   28  C28 UNL     1       9.270   0.503   0.925  1.00  0.00           C  
HETATM   29  C29 UNL     1       7.222  -0.099  -0.183  1.00  0.00           C  
HETATM   30  C30 UNL     1       7.937  -0.511  -1.419  1.00  0.00           C  
HETATM   31  O1  UNL     1       9.290  -0.385  -1.395  1.00  0.00           O  
HETATM   32  P1  UNL     1      10.048  -0.864  -2.804  1.00  0.00           P  
HETATM   33  O2  UNL     1       9.161  -0.477  -3.964  1.00  0.00           O  
HETATM   34  O3  UNL     1      10.249  -2.542  -2.871  1.00  0.00           O  
HETATM   35  O4  UNL     1      11.505  -0.047  -2.951  1.00  0.00           O  
HETATM   36  P2  UNL     1      12.477  -0.234  -1.581  1.00  0.00           P  
HETATM   37  O5  UNL     1      12.132  -1.520  -0.867  1.00  0.00           O  
HETATM   38  O6  UNL     1      12.248   1.026  -0.478  1.00  0.00           O  
HETATM   39  O7  UNL     1      14.109  -0.204  -2.059  1.00  0.00           O  
HETATM   40  H1  UNL     1     -12.375  -1.531  -2.902  1.00  0.00           H  
HETATM   41  H2  UNL     1     -12.830  -1.451  -1.132  1.00  0.00           H  
HETATM   42  H3  UNL     1     -13.621  -0.340  -2.272  1.00  0.00           H  
HETATM   43  H4  UNL     1     -12.533   1.441  -3.331  1.00  0.00           H  
HETATM   44  H5  UNL     1     -10.779   1.262  -3.596  1.00  0.00           H  
HETATM   45  H6  UNL     1     -11.412   2.259  -2.239  1.00  0.00           H  
HETATM   46  H7  UNL     1     -10.746  -0.964  -0.371  1.00  0.00           H  
HETATM   47  H8  UNL     1      -9.612   1.221   0.291  1.00  0.00           H  
HETATM   48  H9  UNL     1      -9.615   1.726  -1.443  1.00  0.00           H  
HETATM   49  H10 UNL     1      -7.429   1.135  -0.765  1.00  0.00           H  
HETATM   50  H11 UNL     1      -7.967  -0.001  -2.029  1.00  0.00           H  
HETATM   51  H12 UNL     1      -7.605  -2.939  -0.273  1.00  0.00           H  
HETATM   52  H13 UNL     1      -8.967  -2.271  -1.158  1.00  0.00           H  
HETATM   53  H14 UNL     1      -9.112  -2.385   0.630  1.00  0.00           H  
HETATM   54  H15 UNL     1      -6.199   0.192   0.728  1.00  0.00           H  
HETATM   55  H16 UNL     1      -6.912  -2.759   1.591  1.00  0.00           H  
HETATM   56  H17 UNL     1      -6.241  -1.501   2.623  1.00  0.00           H  
HETATM   57  H18 UNL     1      -4.702  -2.659   0.233  1.00  0.00           H  
HETATM   58  H19 UNL     1      -4.527  -3.130   1.937  1.00  0.00           H  
HETATM   59  H20 UNL     1      -4.185   0.487   2.828  1.00  0.00           H  
HETATM   60  H21 UNL     1      -2.749  -0.591   3.233  1.00  0.00           H  
HETATM   61  H22 UNL     1      -4.413  -1.105   3.595  1.00  0.00           H  
HETATM   62  H23 UNL     1      -3.154  -1.127  -0.445  1.00  0.00           H  
HETATM   63  H24 UNL     1      -2.229   0.799   1.832  1.00  0.00           H  
HETATM   64  H25 UNL     1      -2.381   1.255   0.082  1.00  0.00           H  
HETATM   65  H26 UNL     1      -0.692  -0.455  -0.531  1.00  0.00           H  
HETATM   66  H27 UNL     1      -0.494  -0.895   1.238  1.00  0.00           H  
HETATM   67  H28 UNL     1      -0.288   2.656   2.147  1.00  0.00           H  
HETATM   68  H29 UNL     1       1.318   1.768   2.399  1.00  0.00           H  
HETATM   69  H30 UNL     1      -0.234   1.015   2.812  1.00  0.00           H  
HETATM   70  H31 UNL     1       0.829   0.962  -1.199  1.00  0.00           H  
HETATM   71  H32 UNL     1       1.567   3.302  -0.968  1.00  0.00           H  
HETATM   72  H33 UNL     1       1.775   3.182   0.776  1.00  0.00           H  
HETATM   73  H34 UNL     1       3.869   3.190  -0.427  1.00  0.00           H  
HETATM   74  H35 UNL     1       3.405   1.790  -1.429  1.00  0.00           H  
HETATM   75  H36 UNL     1       2.688  -0.089   1.588  1.00  0.00           H  
HETATM   76  H37 UNL     1       2.615  -0.273  -0.221  1.00  0.00           H  
HETATM   77  H38 UNL     1       4.053  -0.884   0.652  1.00  0.00           H  
HETATM   78  H39 UNL     1       5.292   2.623   1.144  1.00  0.00           H  
HETATM   79  H40 UNL     1       5.303   1.107   3.281  1.00  0.00           H  
HETATM   80  H41 UNL     1       5.185  -0.315   2.177  1.00  0.00           H  
HETATM   81  H42 UNL     1       7.481   0.161   2.993  1.00  0.00           H  
HETATM   82  H43 UNL     1       7.398   1.830   2.455  1.00  0.00           H  
HETATM   83  H44 UNL     1       9.526   1.241   0.171  1.00  0.00           H  
HETATM   84  H45 UNL     1       9.622   0.893   1.924  1.00  0.00           H  
HETATM   85  H46 UNL     1       9.747  -0.474   0.827  1.00  0.00           H  
HETATM   86  H47 UNL     1       6.115  -0.196  -0.154  1.00  0.00           H  
HETATM   87  H48 UNL     1       7.639  -1.593  -1.572  1.00  0.00           H  
HETATM   88  H49 UNL     1       7.455   0.031  -2.269  1.00  0.00           H  
HETATM   89  H50 UNL     1      10.575  -2.763  -3.777  1.00  0.00           H  
HETATM   90  H51 UNL     1      13.120   1.355  -0.127  1.00  0.00           H  
HETATM   91  H52 UNL     1      14.567  -0.971  -1.626  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    4    4
CONECT    3   43   44   45
CONECT    4    5   46
CONECT    5    6   47   48
CONECT    6    7   49   50
CONECT    7    8    9    9
CONECT    8   51   52   53
CONECT    9   10   54
CONECT   10   11   55   56
CONECT   11   12   57   58
CONECT   12   13   14   14
CONECT   13   59   60   61
CONECT   14   15   62
CONECT   15   16   63   64
CONECT   16   17   65   66
CONECT   17   18   19   19
CONECT   18   67   68   69
CONECT   19   20   70
CONECT   20   21   71   72
CONECT   21   22   73   74
CONECT   22   23   24   24
CONECT   23   75   76   77
CONECT   24   25   78
CONECT   25   26   79   80
CONECT   26   27   81   82
CONECT   27   28   29   29
CONECT   28   83   84   85
CONECT   29   30   86
CONECT   30   31   87   88
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   89
CONECT   35   36
CONECT   36   37   37   38   39
CONECT   38   90
CONECT   39   91
END

HMDB0012188
     RDKit          3D
all-trans-Hexaprenyl diphosphate
 91 90  0  0  0  0  0  0  0  0999 V2000
  -12.6649   -0.8560   -2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5704    0.1360   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5447    1.3306   -2.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6382   -0.0718   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.8363   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1492    0.2928   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596   -0.8627   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   -2.1911   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7134   -0.7720    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2733   -1.8816    1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8469   -2.3070    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950   -1.1841    1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831   -0.5412    2.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -0.6989    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643    0.4262    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -0.1070    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    1.0449    0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2548    1.7137    2.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143    1.4709   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    2.5788   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    2.2430   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    1.2542    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.0943    0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9249    1.5908    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997    0.7234    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0657    0.7785    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512    0.3704    0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2702    0.5028    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2224   -0.0987   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9366   -0.5105   -1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2896   -0.3846   -1.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0481   -0.8643   -2.8039 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1606   -0.4769   -3.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2490   -2.5418   -2.8713 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -0.0468   -2.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4769   -0.2337   -1.5810 P   0  0  0  0  0  5  0  0  0  0  0  0
   12.1323   -1.5198   -0.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2476    1.0265   -0.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1090   -0.2036   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3748   -1.5314   -2.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8302   -1.4509   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6206   -0.3399   -2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5328    1.4407   -3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7787    1.2616   -3.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4121    2.2587   -2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7457   -0.9644   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6118    1.2209    0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    1.7259   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    1.1347   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9667   -0.0008   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6049   -2.9386   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9671   -2.2708   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1123   -2.3849    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1990    0.1924    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120   -2.7590    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2412   -1.5011    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016   -2.6587    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268   -3.1305    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1852    0.4874    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -0.5906    3.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -1.1049    3.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -1.1274   -0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.7986    1.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    1.2550    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.4553   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4943   -0.8948    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.6559    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    1.7680    2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    1.0154    2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8294    0.9622   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    3.3024   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    3.1824    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690    3.1901   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045    1.7899   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6883   -0.0893    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.2726   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0535   -0.8839    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2923    2.6227    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    1.1075    3.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848   -0.3146    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4814    0.1606    2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3981    1.8302    2.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5262    1.2409    0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    0.8925    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7469   -0.4745    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -0.1956   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -1.5926   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554    0.0314   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5754   -2.7625   -3.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1198    1.3551   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5674   -0.9708   -1.6258 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  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  6 50  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 18 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 23 75  1  0
 23 76  1  0
 23 77  1  0
 24 78  1  0
 25 79  1  0
 25 80  1  0
 26 81  1  0
 26 82  1  0
 28 83  1  0
 28 84  1  0
 28 85  1  0
 29 86  1  0
 30 87  1  0
 30 88  1  0
 34 89  1  0
 38 90  1  0
 39 91  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphate	ChEBI
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphoric acid	Generator
all-trans-Hexaprenyl diphosphoric acid	Generator
(E)-Hexaprenyl diphosphate	HMDB

Chemical Formula

C₃₀H₅₂O₇P₂

Average Molecular Weight

586.6772

Monoisotopic Molecular Weight

586.318827042

IUPAC Name

[({[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

{[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid

CAS Registry Number

207513-95-9

SMILES

CC(C)=CCC\C(C)=C\CC\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/C30H52O7P2/c1-25(2)13-8-14-26(3)15-9-16-27(4)17-10-18-28(5)19-11-20-29(6)21-12-22-30(7)23-24-36-39(34,35)37-38(31,32)33/h13,15,17,19,21,23H,8-12,14,16,18,20,22,24H2,1-7H3,(H,34,35)(H2,31,32,33)/b26-15+,27-17+,28-19+,29-21+,30-23+

InChI Key

NGFSMHKFTZROKJ-MMSZMYIBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Bactoprenol diphosphates

Alternative Parents

Substituents

Bactoprenol diphosphate
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

all-trans-polyprenyl diphosphate (CHEBI:17528 )
hexaprenyl diphosphate (CHEBI:17528 )
Polyterpenoids (C01230 )
Bactoprenol diphosphates (LMPR03030005 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.00072 g/L	ALOGPS
logP	5.95	ALOGPS
logP	8.6	ChemAxon
logS	-5.9	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	20	ChemAxon
Refractivity	168.14 m³·mol⁻¹	ChemAxon
Polarizability	67.36 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	237.108	31661259
DarkChem	[M-H]-	224.104	31661259
DeepCCS	[M+H]+	225.191	30932474
DeepCCS	[M-H]-	222.795	30932474
DeepCCS	[M-2H]-	255.678	30932474
DeepCCS	[M+Na]+	231.103	30932474
AllCCS	[M+H]+	246.6	32859911
AllCCS	[M+H-H2O]+	245.2	32859911
AllCCS	[M+NH4]+	247.9	32859911
AllCCS	[M+Na]+	248.3	32859911
AllCCS	[M-H]-	236.8	32859911
AllCCS	[M+Na-2H]-	240.9	32859911
AllCCS	[M+HCOO]-	245.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.6 minutes	32390414
Predicted by Siyang on May 30, 2022	17.9003 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	82.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3818.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	189.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	241.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	150.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	929.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1064.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1768.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	891.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	671.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	748.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	281.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	492.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
all-trans-Hexaprenyl diphosphate	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O	4768.5	Standard polar	33892256
all-trans-Hexaprenyl diphosphate	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O	3426.3	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate	CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O	4053.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
all-trans-Hexaprenyl diphosphate,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	4023.6	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	3221.6	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	4948.9	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	4022.8	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	3229.9	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	4971.3	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	3944.5	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	3288.5	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	4460.4	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3946.5	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3266.5	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4463.6	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3873.1	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3324.2	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3921.4	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	4206.3	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	3363.0	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	5006.3	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	4201.9	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3377.9	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	5022.1	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	4317.6	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3568.5	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	4522.3	Standard polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4320.4	Semi standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3537.3	Standard non polar	33892256
all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4554.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-Hexaprenyl diphosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00tb-7466390000-1a091a15f69aa600fd33	2017-09-01	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 - all-trans-Hexaprenyl diphosphate 10V, Positive-QTOF	splash10-0a4r-0202690000-ca7be5f91d120b34e02f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Positive-QTOF	splash10-0a4i-2312910000-a18bd263c2252df7e12b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Positive-QTOF	splash10-0a59-4439820000-433602f028fdf8312339	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Negative-QTOF	splash10-000i-0400090000-eba550c0908e0bdcc04f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Negative-QTOF	splash10-056r-7900010000-903a330facd80aef97a7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Negative-QTOF	splash10-004i-9000000000-5db7557b14be93fbdd9b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Positive-QTOF	splash10-000i-0100290000-dc5d848846327789fd85	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Positive-QTOF	splash10-0aos-0004930000-e9910289e743569a483c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Positive-QTOF	splash10-020a-1925210000-a29abfabad842bde7acf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Negative-QTOF	splash10-000i-0000090000-8f206fdd3583884650db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Negative-QTOF	splash10-000i-1300190000-fbac398a5a0b0394af5d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Negative-QTOF	splash10-056r-9400000000-c2d5c8e79c928bb87206	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ubiquinone Biosynthesis

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

FDB028840

KNApSAcK ID

Not Available

Chemspider ID

4444089

KEGG Compound ID

C01230

BioCyc ID

ALL-TRANS-HEXAPRENYL-DIPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280413

PDB ID

Not Available

ChEBI ID

17528

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. 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.

Enzymes

Enzyme Details

1. 4-hydroxybenzoate polyprenyltransferase, mitochondrial

General function:: Involved in prenyltransferase activity
Specific function:: Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:: COQ2
Uniprot ID:: Q96H96
Molecular weight:: 45593.67

Reactions

all-trans-Hexaprenyl diphosphate + 4-Hydroxybenzoic acid → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphate	details

Showing metabocard for all-trans-Hexaprenyl diphosphate (HMDB0012188)

MOL for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

3D MOL for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

3D SDF for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

3D-SDF for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

PDB for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

3D PDB for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

SMILES for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

INCHI for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

Structure for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

3D Structure for HMDB0012188 (all-trans-Hexaprenyl diphosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions