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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-06-30 18:40:48 UTC

HMDB ID

HMDB0001285

Secondary Accession Numbers

HMDB0001560
HMDB0002239
HMDB0006506
HMDB01285
HMDB01560
HMDB02239
HMDB06506

Metabolite Identification

Common Name

Geranyl-PP

Description

Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia .

Structure

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

HMDB0001285
     RDKit          3D
Geranyl-PP
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.2722    2.4246    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6120    1.0624    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4320   -0.0931   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.0838    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5474   -0.1701    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177   -0.1221    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -1.1501    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587   -2.5670    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -0.5633   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328   -1.1046   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.6725    0.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    0.0817   -1.1221 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.4506    0.0374   -2.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    1.8009   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.3534   -0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    0.1892    0.6704 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9233    0.9848    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3779    1.1691    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -1.1997    1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    3.1388   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278    2.7078    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2640    2.4657   -0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2482   -0.9006    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5250    0.1663   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.4697   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    2.0316    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0658    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -0.2536   -0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403    0.8919    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832   -0.3617    2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760   -2.9150    1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -3.1657    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927   -2.9322   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    0.5763   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -0.7509   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -2.2379   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.1600   -0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1510    1.8899   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070   -1.8134    1.0480 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  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv1652306302020392D          

 19 18  0  0  0  0            999 V2000
 9987.6417 9985.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.3554 9986.0223    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9986.9260 9986.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.0794 9985.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9449 9986.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.7699 9986.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.2114 9985.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.7950 9986.0345    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4965 9986.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3804 9986.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5066 9985.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2054 9986.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.7816 9985.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4965 9986.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.0666 9986.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.3517 9985.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.6368 9986.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.9219 9985.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.6368 9986.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001285

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+

> <INCHI_KEY>
GVVPGTZRZFNKDS-JXMROGBWSA-N

> <FORMULA>
C10H20O7P2

> <MOLECULAR_WEIGHT>
314.2091

> <EXACT_MASS>
314.068426018

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.51754860324528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.9570187856666668

> <ALOGPS_LOGS>
-2.54

> <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>
72.92789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geranyl diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001285
     RDKit          3D
Geranyl-PP
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.2722    2.4246    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6120    1.0624    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4320   -0.0931   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.0838    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5474   -0.1701    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177   -0.1221    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -1.1501    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587   -2.5670    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -0.5633   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328   -1.1046   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.6725    0.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    0.0817   -1.1221 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.4506    0.0374   -2.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    1.8009   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.3534   -0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    0.1892    0.6704 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9233    0.9848    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3779    1.1691    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -1.1997    1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    3.1388   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278    2.7078    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2640    2.4657   -0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2482   -0.9006    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5250    0.1663   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.4697   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    2.0316    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0658    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -0.2536   -0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403    0.8919    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832   -0.3617    2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760   -2.9150    1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -3.1657    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927   -2.9322   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    0.5763   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -0.7509   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -2.2379   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.1600   -0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1510    1.8899   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070   -1.8134    1.0480 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  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 30-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-20         0                                  
HETATM    1  O   UNK     0    8643.5988639.806   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0    8644.9308640.575   0.000  0.00  0.00           P+0
HETATM    3  C   UNK     0    8642.2628640.575   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8646.2818639.829   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8644.1648641.908   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8645.7048641.908   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8640.9288639.806   0.000  0.00  0.00           C+0
HETATM    8  P   UNK     0    8647.6178640.598   0.000  0.00  0.00           P+0
HETATM    9  C   UNK     0    8639.5938640.575   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8646.8438641.931   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8648.9468639.829   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8648.3838641.931   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8638.2598639.806   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8639.5938642.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8636.9248640.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8635.5908639.806   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8634.2558640.575   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8632.9218639.806   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8634.2558642.116   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    9                                                       
CONECT    8    4   10   11   12                                             
CONECT    9    7   13   14                                                  
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9   15                                                       
CONECT   14    9                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0001285
HETATM    1  C1  UNL     1      -5.272   2.425   0.287  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.612   1.062   0.104  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.432  -0.093  -0.198  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.297   1.084   0.216  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.547  -0.170   0.069  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.318  -0.122   1.008  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.358  -1.150   0.388  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.559  -2.567   0.381  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.683  -0.563  -0.137  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.833  -1.105  -0.820  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.948  -0.672   0.001  1.00  0.00           O  
HETATM   12  P1  UNL     1       3.982   0.082  -1.122  1.00  0.00           P  
HETATM   13  O2  UNL     1       3.451   0.037  -2.522  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.924   1.801  -0.640  1.00  0.00           O  
HETATM   15  O4  UNL     1       5.542  -0.353  -0.902  1.00  0.00           O  
HETATM   16  P2  UNL     1       6.009   0.189   0.670  1.00  0.00           P  
HETATM   17  O5  UNL     1       4.923   0.985   1.334  1.00  0.00           O  
HETATM   18  O6  UNL     1       7.378   1.169   0.499  1.00  0.00           O  
HETATM   19  O7  UNL     1       6.347  -1.200   1.623  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.546   3.139  -0.319  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.328   2.708   1.327  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.264   2.466  -0.237  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.248  -0.901   0.502  1.00  0.00           H  
HETATM   24  H5  UNL     1      -6.525   0.166  -0.236  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.140  -0.470  -1.246  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.808   2.032   0.476  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.115  -1.066   0.300  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.121  -0.254  -0.969  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.940   0.892   0.981  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.583  -0.362   2.011  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.376  -2.915   1.001  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.352  -3.166   0.706  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.693  -2.932  -0.680  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.754   0.576  -0.027  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.899  -0.751  -1.824  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.922  -2.238  -0.812  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.077   2.160  -0.962  1.00  0.00           H  
HETATM   38  H19 UNL     1       7.151   1.890  -0.135  1.00  0.00           H  
HETATM   39  H20 UNL     1       6.907  -1.813   1.048  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    4
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    9    9
CONECT    8   31   32   33
CONECT    9   10   34
CONECT   10   11   35   36
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   37
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   38
CONECT   19   39
END

HMDB0001285
     RDKit          3D
Geranyl-PP
 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.2722    2.4246    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6120    1.0624    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4320   -0.0931   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.0838    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5474   -0.1701    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177   -0.1221    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -1.1501    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587   -2.5670    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -0.5633   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328   -1.1046   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.6725    0.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    0.0817   -1.1221 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.4506    0.0374   -2.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    1.8009   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.3534   -0.9020 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    0.1892    0.6704 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9233    0.9848    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3779    1.1691    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -1.1997    1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    3.1388   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278    2.7078    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2640    2.4657   -0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2482   -0.9006    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5250    0.1663   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.4697   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    2.0316    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0658    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -0.2536   -0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403    0.8919    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832   -0.3617    2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760   -2.9150    1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -3.1657    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927   -2.9322   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    0.5763   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -0.7509   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -2.2379   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.1600   -0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1510    1.8899   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070   -1.8134    1.0480 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  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Geranyl pyrophosphate	ChEBI
Polyisopentenylpyrophosphate	Kegg
Polyisopentenyldiphosphate	Kegg
trans-Polyisopentenyldiphosphate	Kegg
Polyprenyl diphosphate	Kegg
Geranyl pyrophosphoric acid	Generator
Polyisopentenylpyrophosphoric acid	Generator
Polyisopentenyldiphosphoric acid	Generator
trans-Polyisopentenyldiphosphoric acid	Generator
Polyprenyl diphosphoric acid	Generator
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate	HMDB
Geranyl diphosphate	HMDB
Geranyl-diphosphate	HMDB
Geranyl-pyrophosphate	HMDB
Monoterpenyl diphosphate	HMDB
Neryl diphosphate	HMDB
trans-Geranyl pyrophosphate	HMDB
P-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]diphosphoric acid	HMDB
trans-geranyl-PP	HMDB

Chemical Formula

C₁₀H₂₀O₇P₂

Average Molecular Weight

314.2091

Monoisotopic Molecular Weight

314.068426018

IUPAC Name

[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

geranyl diphosphate

CAS Registry Number

763-10-0

SMILES

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

InChI Identifier

InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+

InChI Key

GVVPGTZRZFNKDS-JXMROGBWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid phosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoterpenoid
Isoprenoid phosphate
Acyclic monoterpenoid
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

polyprenol diphosphate (CHEBI:17211 )
Acyclic monoterpenoids (C00341 )
Linear monoterpenes (C00341 )
Acyclic monoterpenoids (LMPR0102010001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001285)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001285)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001285)

Source

Exogenous

Exogenous (HMDB: HMDB0001285)

Food

Food (HMDB: HMDB0001285)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0001285)

Plant

Animal

Animal (HMDB: HMDB0001285)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001285)

Biochemical pathway

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0001285)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001285)
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid Biosynthesis (PathBank: SMP0121325)
Steroid Biosynthesis (PathBank: SMP0087326)
Terpenoid Backbone Biosynthesis (PathBank: SMP0121210)
Mevalonate Pathway (PathBank: SMP0121209)
Steroid Biosynthesis (PathBank: SMP0002381)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Epoxysqualene Biosynthesis (PathBank: SMP0012042)
Farnesene Biosynthesis (PathBank: SMP0012049)
Monoterpenoid Biosynthesis (PathBank: SMP0014204)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)
MEP/DOXP Pathway (PathBank: SMP0121208)

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0001285)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
CHILD Syndrome (PathBank: SMP0120464)
Wolman Disease (PathBank: SMP0120576)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Lipid metabolism pathway (HMDB: HMDB0001285)

Cellular process

Cell signaling (HMDB: HMDB0001285)

Biochemical process

Lipid transport (HMDB: HMDB0001285)

Role

Biological role

Energy source (HMDB: HMDB0001285)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001285)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	167.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000241

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.9 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.96	ChemAxon
logS	-2.5	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	8	ChemAxon
Refractivity	72.93 m³·mol⁻¹	ChemAxon
Polarizability	28.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	176.783	31661259
DarkChem	[M-H]-	168.547	31661259
AllCCS	[M+H]+	173.604	32859911
AllCCS	[M-H]-	167.014	32859911
DeepCCS	[M+H]+	160.14	30932474
DeepCCS	[M-H]-	157.316	30932474
DeepCCS	[M-2H]-	191.221	30932474
DeepCCS	[M+Na]+	167.637	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.6	32859911
AllCCS	[M+NH4]+	176.4	32859911
AllCCS	[M+Na]+	177.2	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Geranyl-PP	CC(C)=CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O	3718.2	Standard polar	33892256
Geranyl-PP	CC(C)=CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O	2024.2	Standard non polar	33892256
Geranyl-PP	CC(C)=CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O	2407.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Geranyl-PP,1TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2299.9	Semi standard non polar	33892256
Geranyl-PP,1TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2062.8	Standard non polar	33892256
Geranyl-PP,1TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O	3125.1	Standard polar	33892256
Geranyl-PP,1TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2283.6	Semi standard non polar	33892256
Geranyl-PP,1TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2064.8	Standard non polar	33892256
Geranyl-PP,1TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C	3162.0	Standard polar	33892256
Geranyl-PP,2TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2320.5	Semi standard non polar	33892256
Geranyl-PP,2TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2116.6	Standard non polar	33892256
Geranyl-PP,2TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2807.6	Standard polar	33892256
Geranyl-PP,2TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2323.7	Semi standard non polar	33892256
Geranyl-PP,2TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2114.0	Standard non polar	33892256
Geranyl-PP,2TMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2815.4	Standard polar	33892256
Geranyl-PP,3TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2342.7	Semi standard non polar	33892256
Geranyl-PP,3TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2174.2	Standard non polar	33892256
Geranyl-PP,3TMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2495.2	Standard polar	33892256
Geranyl-PP,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2531.3	Semi standard non polar	33892256
Geranyl-PP,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2234.5	Standard non polar	33892256
Geranyl-PP,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	3265.1	Standard polar	33892256
Geranyl-PP,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2516.0	Semi standard non polar	33892256
Geranyl-PP,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2248.2	Standard non polar	33892256
Geranyl-PP,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3300.4	Standard polar	33892256
Geranyl-PP,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2732.1	Semi standard non polar	33892256
Geranyl-PP,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2447.5	Standard non polar	33892256
Geranyl-PP,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2980.3	Standard polar	33892256
Geranyl-PP,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2739.2	Semi standard non polar	33892256
Geranyl-PP,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2408.5	Standard non polar	33892256
Geranyl-PP,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3000.0	Standard polar	33892256
Geranyl-PP,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2924.4	Semi standard non polar	33892256
Geranyl-PP,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2613.0	Standard non polar	33892256
Geranyl-PP,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2757.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Geranyl-PP GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9640000000-9ce32c835bdcfa97fa15	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Geranyl-PP GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Geranyl-PP GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 6V, negative-QTOF	splash10-0002-0090000000-b5ca864b0ba8818ad627	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 8V, negative-QTOF	splash10-0002-0090000000-c7f7c5c529a56d532304	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 11V, negative-QTOF	splash10-0002-3390000000-010bee66d1e4bd685e95	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 14V, negative-QTOF	splash10-004i-9440000000-13e525f66230aae586a2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 17V, negative-QTOF	splash10-004i-9200000000-a9da8f03edb73eec50bf	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 20V, negative-QTOF	splash10-004i-9100000000-fe3060700600ee72f8dd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 23V, negative-QTOF	splash10-004i-9000000000-15de26c097afd86b7007	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 27V, negative-QTOF	splash10-004i-9000000000-bcc45bf0bf3bbb46af13	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 33V, negative-QTOF	splash10-004i-9000000000-b8b56dc9ea06c2ce52b5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP n/a 21V, negative-QTOF	splash10-0a4i-0900000000-f2685d197409ed952f02	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP n/a 21V, negative-QTOF	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP n/a 21V, negative-QTOF	splash10-0a4i-0900000000-60b9e910670cbc6ebe0c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP n/a 21V, negative-QTOF	splash10-0bt9-0390000000-6532032bbb594aa54d9c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 5V, negative-QTOF	splash10-03di-0009000000-3bcab8c3688c96a4cec5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 7V, negative-QTOF	splash10-03di-2009000000-42fa98db20ae4d6f687e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 9V, negative-QTOF	splash10-01t9-9005000000-44618200345aed481b48	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 12V, negative-QTOF	splash10-004i-9000000000-befed7a961a777eb5f66	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 15V, negative-QTOF	splash10-004i-9000000000-8afaaf750b51acbd1a01	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Geranyl-PP Orbitrap 18V, negative-QTOF	splash10-004i-9000000000-b5b3b346fecad6ae473d	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 10V, Positive-QTOF	splash10-00kr-1953000000-e5ee3340554c9ecac23e	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 20V, Positive-QTOF	splash10-000i-5910000000-82bcd2195a53b847981c	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 40V, Positive-QTOF	splash10-0gc0-9400000000-f87d391f1b3c01743515	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 10V, Negative-QTOF	splash10-03di-0509000000-43083a162145718cd977	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 20V, Negative-QTOF	splash10-004i-9500000000-053b6323e620a16328a8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl-PP 40V, Negative-QTOF	splash10-004i-9000000000-4faed4c921d605619caf	2015-09-15	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

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02552

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Geranyl_pyrophosphate

METLIN ID

6134

PubChem Compound

445995

PDB ID

Not Available

ChEBI ID

17211

Food Biomarker Ontology

Not Available

VMH ID

GRDP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Runquist M; Ericsson J; Thelin A; Chojnacki T; Dallner G Biosynthesis of trans,trans,trans-geranylgeranyl diphosphate by the cytosolic fraction from rat tissues. Biochemical and biophysical research communications (1992), 186(1), 157-65.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kavanagh KL, Guo K, Dunford JE, Wu X, Knapp S, Ebetino FH, Rogers MJ, Russell RG, Oppermann U: The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs. Proc Natl Acad Sci U S A. 2006 May 16;103(20):7829-34. Epub 2006 May 9. [PubMed:16684881 ]
Micali E, Chehade KA, Isaacs RJ, Andres DA, Spielmann HP: Protein farnesyltransferase isoprenoid substrate discrimination is dependent on isoprene double bonds and branched methyl groups. Biochemistry. 2001 Oct 16;40(41):12254-65. [PubMed:11591144 ]
Holstein SA, Hohl RJ: Isoprenoids: remarkable diversity of form and function. Lipids. 2004 Apr;39(4):293-309. [PubMed:15357017 ]
Gan X, Kaplan R, Menke JG, MacNaul K, Chen Y, Sparrow CP, Zhou G, Wright SD, Cai TQ: Dual mechanisms of ABCA1 regulation by geranylgeranyl pyrophosphate. J Biol Chem. 2001 Dec 28;276(52):48702-8. Epub 2001 Oct 18. [PubMed:11641412 ]
Sagami H, Ogura K: [A new development in isoprenoid biochemistry brought by the discovery of prenylated proteins]. Seikagaku. 1994 Dec;66(12):1488-501. [PubMed:7884273 ]
Loza-Tavera H: Monoterpenes in essential oils. Biosynthesis and properties. Adv Exp Med Biol. 1999;464:49-62. [PubMed:10335385 ]
Barnard GF, Popjak G: Human liver prenyltransferase and its characterization. Biochim Biophys Acta. 1981 Sep 15;661(1):87-99. [PubMed:7295734 ]
Pont F, Luciani B, Belmant C, Fournie JJ: Characterization of phosphoantigens by high-performance anion-exchange chromatography-electrospray ionization ion trap mass spectrometry and nanoelectrospray ionization ion trap mass spectrometry. Anal Chem. 2001 Aug 1;73(15):3562-9. [PubMed:11510819 ]
Smit A, Mushegian A: Biosynthesis of isoprenoids via mevalonate in Archaea: the lost pathway. Genome Res. 2000 Oct;10(10):1468-84. [PubMed:11042147 ]

Enzymes

Enzyme Details

1. Geranylgeranyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:: GGPS1
Uniprot ID:: O95749
Molecular weight:: 34870.625

Reactions

Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PP	details
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphate	details

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Farnesyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:: FDPS
Uniprot ID:: P14324
Molecular weight:: 48275.03

Reactions

Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PP	details
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphate	details

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

3. 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

Geranyl-PP + 4-Hydroxybenzoic acid → 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate	details

Showing metabocard for Geranyl-PP (HMDB0001285)

MOL for HMDB0001285 (Geranyl-PP)

3D MOL for HMDB0001285 (Geranyl-PP)

3D SDF for HMDB0001285 (Geranyl-PP)

3D-SDF for HMDB0001285 (Geranyl-PP)

PDB for HMDB0001285 (Geranyl-PP)

3D PDB for HMDB0001285 (Geranyl-PP)

SMILES for HMDB0001285 (Geranyl-PP)

INCHI for HMDB0001285 (Geranyl-PP)

Structure for HMDB0001285 (Geranyl-PP)

3D Structure for HMDB0001285 (Geranyl-PP)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

Reactions

References

Reactions