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Showing NP-Card for Dimethylallylpyrophosphate (NP0001420)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:53 UTC
NP-MRD IDNP0001420
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethylallylpyrophosphate
DescriptionDimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphoric acid, 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. Dimethylallylpyrophosphate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001420 (Dimethylallylpyrophosphate)


  Mrv1652306252021212D          

 14 13  0  0  0  0            999 V2000
10023.959510023.0458    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10024.683410022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.244810022.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.549010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.374010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.397210023.0581    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10022.529810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.984610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.110810022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.809610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.814910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.384910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.8716    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
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
Download

3D MOL for NP0001420 (Dimethylallylpyrophosphate)

HMDB0001120
     RDKit          3D
Dimethylallylpyrophosphate
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.0255   -1.3682    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -0.1084   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524   -0.1467    0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    1.0441   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    1.2191   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.0315   -0.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5795    0.1710   -0.4427 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9766    1.6109   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -0.6939   -1.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.4606    0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9252   -0.2728    1.0232 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.4297   -1.0586    2.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3771    1.3391    1.2702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952   -0.8966   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.1859    0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819   -1.7068   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357   -1.3111    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.0295    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292    0.8036    0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -0.0563   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639    1.9241   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    1.6201   -1.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3486    1.9467    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.7246   -2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    1.8340    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473   -1.5242   -0.7667 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  2  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  9 24  1  0
 13 25  1  0
 14 26  1  0
M  END
Download

3D SDF for NP0001420 (Dimethylallylpyrophosphate)


  Mrv1652306252021212D          

 14 13  0  0  0  0            999 V2000
10023.959510023.0458    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10024.683410022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.244810022.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.549010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.374010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.397210023.0581    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10022.529810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.984610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.110810022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.809610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.814910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.384910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.8716    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
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCOP(O)(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)

> <INCHI_KEY>
CBIDRCWHNCKSTO-UHFFFAOYSA-N

> <FORMULA>
C5H12O7P2

> <MOLECULAR_WEIGHT>
246.0921

> <EXACT_MASS>
246.005825762

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.189525286748115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
0.2973045106666672

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2043412500331905

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.767219152287395

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
49.1253

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylallyl diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001420 (Dimethylallylpyrophosphate)

HMDB0001120
     RDKit          3D
Dimethylallylpyrophosphate
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.0255   -1.3682    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -0.1084   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524   -0.1467    0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    1.0441   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    1.2191   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.0315   -0.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5795    0.1710   -0.4427 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9766    1.6109   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -0.6939   -1.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.4606    0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9252   -0.2728    1.0232 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.4297   -1.0586    2.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3771    1.3391    1.2702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952   -0.8966   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.1859    0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819   -1.7068   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357   -1.3111    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.0295    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292    0.8036    0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -0.0563   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639    1.9241   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    1.6201   -1.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3486    1.9467    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.7246   -2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    1.8340    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473   -1.5242   -0.7667 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  2  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  9 24  1  0
 13 25  1  0
 14 26  1  0
M  END
Download

PDB for NP0001420 (Dimethylallylpyrophosphate)

HEADER    PROTEIN                                 25-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-20         0                                  
HETATM    1  P   UNK     0    8711.3918709.686   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0    8712.7428708.940   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8710.0578708.917   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8710.6258711.019   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8712.1658711.019   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8714.0758709.708   0.000  0.00  0.00           P+0
HETATM    7  C   UNK     0    8708.7228709.686   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8713.3058711.042   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8715.4078708.940   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8714.8458711.042   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8707.3888708.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8706.0538709.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8704.7188708.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8706.0538711.227   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    8    9   10                                             
CONECT    7    3   11                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
Download

3D PDB for NP0001420 (Dimethylallylpyrophosphate)

COMPND    HMDB0001120
HETATM    1  C1  UNL     1       2.026  -1.368   0.164  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.738  -0.108  -0.084  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.252  -0.147   0.028  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.205   1.044  -0.391  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.746   1.219  -0.531  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.100   0.031  -0.296  1.00  0.00           O  
HETATM    7  P1  UNL     1      -1.580   0.171  -0.443  1.00  0.00           P  
HETATM    8  O2  UNL     1      -1.977   1.611  -0.664  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.067  -0.694  -1.813  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.264  -0.461   0.956  1.00  0.00           O  
HETATM   11  P2  UNL     1      -3.925  -0.273   1.023  1.00  0.00           P  
HETATM   12  O5  UNL     1      -4.430  -1.059   2.213  1.00  0.00           O  
HETATM   13  O6  UNL     1      -4.377   1.339   1.270  1.00  0.00           O  
HETATM   14  O7  UNL     1      -4.695  -0.897  -0.348  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.770  -2.186   0.400  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.482  -1.707  -0.758  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.336  -1.311   1.050  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.584  -1.030   0.580  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.529   0.804   0.568  1.00  0.00           H  
HETATM   20  H6  UNL     1       4.654  -0.056  -0.993  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.864   1.924  -0.553  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.469   1.620  -1.542  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.349   1.947   0.244  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.310  -0.725  -2.456  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.431   1.834   0.422  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.047  -1.524  -0.767  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4    4
CONECT    3   18   19   20
CONECT    4    5   21
CONECT    5    6   22   23
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   24
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   25
CONECT   14   26
END
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SMILES for NP0001420 (Dimethylallylpyrophosphate)

CC(C)=CCOP(O)(=O)OP(O)(O)=O
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INCHI for NP0001420 (Dimethylallylpyrophosphate)

InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)
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View in JSmol
Synonyms
ValueSource
2-Isopentenyl diphosphateChEBI
3,3-Dimethylallyl pyrophosphateChEBI
3-Methylbut-2-enyl phosphono hydrogen phosphateChEBI
delta-Prenyl diphosphateChEBI
delta2-Isopentenyl diphosphateChEBI
Dimethylallyl diphosphateChEBI
Dimethylallyl pyrophosphateChEBI
DMAPPChEBI
Monoprenyl diphosphateChEBI
Prenol pyrophosphateChEBI
Prenyl diphosphateKegg
2-Isopentenyl diphosphoric acidGenerator
3,3-Dimethylallyl pyrophosphoric acidGenerator
3-Methylbut-2-enyl phosphono hydrogen phosphoric acidGenerator
delta-Prenyl diphosphoric acidGenerator
Δ-prenyl diphosphateGenerator
Δ-prenyl diphosphoric acidGenerator
delta2-Isopentenyl diphosphoric acidGenerator
Δ2-isopentenyl diphosphateGenerator
Δ2-isopentenyl diphosphoric acidGenerator
Dimethylallyl diphosphoric acidGenerator
Dimethylallyl pyrophosphoric acidGenerator
Monoprenyl diphosphoric acidGenerator
Prenol pyrophosphoric acidGenerator
Prenyl diphosphoric acidGenerator
Dimethylallylpyrophosphoric acidGenerator
1,1-Dimethyl-4-phenylpiperazinium iodideHMDB
3-Methyl-2-buten-1-ol pyrophosphateHMDB
3-Methyl-2-buten-1-ol trihydrogen pyrophosphateHMDB
3-Methyl-2-butenyl pyrophosphateHMDB
3-Methylbut-2-enyl pyrophosphateHMDB
Delta2-Isopentenyl-diphosphateHMDB
Dimethylallyl-diphosphateHMDB
Dimethylallyl-PPHMDB
Dimethylallyl-ppiHMDB
Dimethylallyl-pyrophosphateHMDB
Diphosphoric acid mono(3-methyl-2-butenyl) esterHMDB
DMPPHMDB
IPEHMDB
Prenyl-diphosphateHMDB
3,3-Dimethylallyl pyrophosphate, (14)C-labeledHMDB
DMADP CPDHMDB
3-Methyl-2-butenyl trihydrogen diphosphateHMDB
gamma,gamma-Dimethylallyl pyrophosphateHMDB
Γ,γ-dimethylallyl pyrophosphateHMDB
DimethylallylpyrophosphateHMDB
Chemical FormulaC5H12O7P2
Average Mass246.0921 Da
Monoisotopic Mass246.00583 Da
IUPAC Name({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional Namedimethylallyl diphosphate
CAS Registry Number358-72-5
SMILES
CC(C)=CCO[P@](O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)
InChI KeyCBIDRCWHNCKSTO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Asparagus racemosusKNApSAcK Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clausena lansiumKNApSAcK Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaKNApSAcK Database
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Polygonum minusKNApSAcK Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stevia rebaudianaKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Taxus fuanaKNApSAcK Database
Taxus yunnanensisKNApSAcK Database
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Aureococcus anaphagefferensKNApSAcK Database
Phaeodactylum tricornutumKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassIsoprenoid phosphates
Direct ParentIsoprenoid phosphates
Alternative Parents
Substituents
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.54 g/LALOGPS
logP0.3ALOGPS
logP0.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.13 m³·mol⁻¹ChemAxon
Polarizability19.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001120
DrugBank IDDB01785
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030829
KNApSAcK IDC00007294
Chemspider ID627
KEGG Compound IDC00235
BioCyc IDCPD-4211
BiGG ID131960
Wikipedia LinkDimethylallyl pyrophosphate
METLIN ID6016
PubChem Compound647
PDB IDNot Available
ChEBI ID16057
Good Scents IDNot Available
References
General References
  1. Smith AS, Smid SD: Impaired capsaicin and neurokinin-evoked colonic motility in inflammatory bowel disease. J Gastroenterol Hepatol. 2005 May;20(5):697-704. [PubMed:15853981 ]
  2. Fisher AJ, Rosenstiel TN, Shirk MC, Fall R: Nonradioactive assay for cellular dimethylallyl diphosphate. Anal Biochem. 2001 May 15;292(2):272-9. doi: 10.1006/abio.2001.5079. [PubMed:11355861 ]
  3. Bang S, Yoo S, Yang TJ, Cho H, Hwang SW: Nociceptive and pro-inflammatory effects of dimethylallyl pyrophosphate via TRPV4 activation. Br J Pharmacol. 2012 Jun;166(4):1433-43. doi: 10.1111/j.1476-5381.2012.01884.x. [PubMed:22300296 ]
  4. Weise SE, Li Z, Sutter AE, Corrion A, Banerjee A, Sharkey TD: Measuring dimethylallyl diphosphate available for isoprene synthesis. Anal Biochem. 2013 Apr 1;435(1):27-34. doi: 10.1016/j.ab.2012.11.031. Epub 2012 Dec 19. [PubMed:23262281 ]