Showing metabocard for Dimethylallylpyrophosphate (MMDBc0029562)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:32:23 UTC
Update Date2022-08-31 13:43:50 UTC
Metabolite IDMMDBc0029562
Metabolite Identification
Common NameDimethylallylpyrophosphate
DescriptionDimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5a80061288>


  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 #<Metabolite:0x00007f5a80061288>

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 #<Metabolite:0x00007f5a80061288>


  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>
MMDBc0029562

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f5a80061288>

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 #<Metabolite:0x00007f5a80061288>

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 #<Metabolite:0x00007f5a80061288>

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 #<Metabolite:0x00007f5a80061288>

CC(C)=CCOP(O)(=O)OP(O)(O)=O
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INCHI for #<Metabolite:0x00007f5a80061288>

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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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
Molecular FormulaC5H12O7P2
Average Mass246.0921
Monoisotopic Mass246.005825762
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