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Showing metabocard for Dimethylallylpyrophosphate (HMDB0001120)

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:28 UTC
HMDB IDHMDB0001120
Secondary Accession Numbers
  • HMDB0002101
  • HMDB01120
  • HMDB02101
Metabolite 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
Data?1593112916
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001120 (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 HMDB0001120 (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 HMDB0001120 (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>
HMDB0001120

> <DATABASE_NAME>
hmdb

> <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 HMDB0001120 (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 HMDB0001120 (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
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3D PDB for HMDB0001120 (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 HMDB0001120 (Dimethylallylpyrophosphate)

CC(C)=CCOP(O)(=O)OP(O)(O)=O
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INCHI for HMDB0001120 (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 JSmolView NMR AssignmentsView Stereo Labels
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
DimethylallylpyrophosphateHMDB
gamma,gamma-Dimethylallyl pyrophosphateHMDB
γ,γ-Dimethylallyl pyrophosphateHMDB
Chemical FormulaC5H12O7P2
Average Molecular Weight246.0921
Monoisotopic Molecular Weight246.005825762
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)=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 KeyCBIDRCWHNCKSTO-UHFFFAOYSA-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.
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point234 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available143.096http://allccs.zhulab.cn/database/detail?ID=AllCCS00000238
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.65331661259
DarkChem[M-H]-148.62831661259
AllCCS[M+H]+153.32932859911
AllCCS[M-H]-145.67632859911
DeepCCS[M+H]+135.330932474
DeepCCS[M-H]-131.47230932474
DeepCCS[M-2H]-169.17130932474
DeepCCS[M+Na]+144.56130932474
AllCCS[M+H]+153.332859911
AllCCS[M+H-H2O]+149.932859911
AllCCS[M+NH4]+156.532859911
AllCCS[M+Na]+157.432859911
AllCCS[M-H]-145.732859911
AllCCS[M+Na-2H]-147.032859911
AllCCS[M+HCOO]-148.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DimethylallylpyrophosphateCC(C)=CCOP(O)(=O)OP(O)(O)=O3264.5Standard polar33892256
DimethylallylpyrophosphateCC(C)=CCOP(O)(=O)OP(O)(O)=O1661.1Standard non polar33892256
DimethylallylpyrophosphateCC(C)=CCOP(O)(=O)OP(O)(O)=O1963.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dimethylallylpyrophosphate,1TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O1934.5Semi standard non polar33892256
Dimethylallylpyrophosphate,1TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O1788.9Standard non polar33892256
Dimethylallylpyrophosphate,1TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O2644.6Standard polar33892256
Dimethylallylpyrophosphate,1TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C1913.0Semi standard non polar33892256
Dimethylallylpyrophosphate,1TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C1775.7Standard non polar33892256
Dimethylallylpyrophosphate,1TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C2675.7Standard polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C1942.1Semi standard non polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C1857.7Standard non polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2352.1Standard polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1949.6Semi standard non polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1848.6Standard non polar33892256
Dimethylallylpyrophosphate,2TMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2359.9Standard polar33892256
Dimethylallylpyrophosphate,3TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1964.7Semi standard non polar33892256
Dimethylallylpyrophosphate,3TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1913.7Standard non polar33892256
Dimethylallylpyrophosphate,3TMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2115.5Standard polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2176.2Semi standard non polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O1977.1Standard non polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2795.3Standard polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2159.4Semi standard non polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C1976.7Standard non polar33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2831.3Standard polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2355.7Semi standard non polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2220.0Standard non polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2584.5Standard polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2366.6Semi standard non polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2184.5Standard non polar33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2601.7Standard polar33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1CC(C)=CCOP(=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)C2546.4Semi standard non polar33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1CC(C)=CCOP(=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)C2364.8Standard non polar33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1CC(C)=CCOP(=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)C2417.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylallylpyrophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9700000000-678abe159a77eee761ec2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylallylpyrophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylallylpyrophosphate n/a 17V, negative-QTOFsplash10-004i-3690000000-be82b5d8f3a1d675c6de2020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 10V, Positive-QTOFsplash10-014j-9660000000-6e2c34b818f993a966d72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 20V, Positive-QTOFsplash10-014i-9200000000-08a00604e05fbe36065b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 40V, Positive-QTOFsplash10-014i-9100000000-01b0ee5834d30012257b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 10V, Negative-QTOFsplash10-0006-0490000000-3b55dbb5fc89be39fcb42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 20V, Negative-QTOFsplash10-004i-9510000000-3521e5fb3dcbf2e3590e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 40V, Negative-QTOFsplash10-004i-9000000000-15ed4ecee7cc175e38332015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 10V, Positive-QTOFsplash10-0002-3290000000-0d2c2679aff41e5a2aa82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 20V, Positive-QTOFsplash10-014j-9100000000-1ca46da447e4b1c422222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 40V, Positive-QTOFsplash10-0002-9000000000-a94de2be1fc80e7f3ca72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 10V, Negative-QTOFsplash10-0006-0490000000-d1cdea0da4ab0affcc512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 20V, Negative-QTOFsplash10-056s-9600000000-f42e0441eb797a5faf852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylallylpyrophosphate 40V, Negative-QTOFsplash10-056r-9700000000-c8d7613f7f9dc6aa7e472021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01785
Phenol Explorer Compound IDNot Available
FooDB IDFDB022434
KNApSAcK IDC00007294
Chemspider ID627
KEGG Compound IDC00235
BioCyc IDCPD-4211
BiGG ID131960
Wikipedia LinkDimethylallyl pyrophosphate
METLIN ID6016
PubChem Compound647
PDB IDNot Available
ChEBI ID16057
Food Biomarker OntologyNot Available
VMH IDDMPP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]

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-PPdetails
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-PPdetails
Enzyme Details
3. Isopentenyl-diphosphate Delta-isomerase 2
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:
IDI2
Uniprot ID:
Q9BXS1
Molecular weight:
26752.33
Reactions
Isopentenyl pyrophosphate → Dimethylallylpyrophosphatedetails
Enzyme Details
4. Isopentenyl-diphosphate Delta-isomerase 1
General function:
Involved in isopentenyl-diphosphate delta-isomerase activity
Specific function:
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:
IDI1
Uniprot ID:
Q13907
Molecular weight:
32485.165
Reactions
Isopentenyl pyrophosphate → Dimethylallylpyrophosphatedetails
Enzyme Details
5. tRNA dimethylallyltransferase, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the transfer of a dimethylallyl group onto the adenine at position 37 of both cytosolic and mitochondrial tRNAs, leading to the formation of N6-(dimethylallyl)adenosine (i(6)A).
Gene Name:
TRIT1
Uniprot ID:
Q9H3H1
Molecular weight:
52724.84
Reactions
Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-dimethylallyladenosinedetails
Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-isopentenyladenosinedetails