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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:30 UTC

Update Date

2021-09-14 15:20:03 UTC

HMDB ID

HMDB0001981

Secondary Accession Numbers

HMDB01981

Metabolite Identification

Common Name

(R)-Mevalonic acid-5-pyrophosphate

Description

(R)-Mevalonic acid-5-pyrophosphate (mevalonate 5-diphosphate) is a directly synthesized product of mevalonate phosphate that is essential for cell proliferation. (PMID 2211719 ). It is a substrate for mevalonate-5-diphosphate decarboxylase, the third enzyme involved in the biosynthesis of cholesterol from mevalonic acid. This enzyme catalyzes the reaction of mevalonate 5-diphosphate (MVADP) with ATP to produce isopentenyl diphosphate, ADP, CO2, and inorganic phosphate. The overall reaction involves an anti elimination of the tertiary hydroxyl and carboxyl groups. This metabolite participates both in the biosynthesis of cholesterol and fatty acid mechanism, through which interpathway regulation could take place between the cholesterol and FA cascades. (PMID 8769113 ).

Structure

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

HMDB0001981
     RDKit          3D
(R)-Mevalonic acid-5-pyrophosphate
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.5477    1.9520    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862    0.4917    0.3836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5950   -0.0379    1.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.2859   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -0.2890   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.8262    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -0.7329   -0.1667 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5955    0.3559   -1.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -2.2488   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -0.4379    1.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7940    0.1015    0.6675 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.7913    0.1496    1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    1.6274   -0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2521   -0.9582   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    0.5061    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0861   -0.8262    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -1.8375    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4732   -1.0071    0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    2.1252   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    2.2768    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    2.6231    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882   -0.9916    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    0.1957   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -1.3060   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -0.9547   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    0.6823   -1.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -2.2764   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    2.3440    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929   -1.8112   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468    0.8807   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    1.2167    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -0.7010   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  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
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END

Untitled Document-5
  Mrv1652309042000252D          

 18 17  0  0  0  0            999 V2000
   -2.4454    1.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    0.5635    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.6740    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.6740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8414   -1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -0.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
  2 12  2  0  0  0  0
  2 13  1  0  0  0  0
  4 14  2  0  0  0  0
  4 15  1  0  0  0  0
  8 16  1  1  0  0  0
  8 17  1  6  0  0  0
 10 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001981

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m0/s1

> <INCHI_KEY>
SIGQQUBJQXSAMW-LURJTMIESA-N

> <FORMULA>
C6H14O10P2

> <MOLECULAR_WEIGHT>
308.1169

> <EXACT_MASS>
308.006219692

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.58891470571585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-1.638744069

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.1625026122597153

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7759296675393568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.923623985716116

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
56.257200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrophosphomevalonate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001981
     RDKit          3D
(R)-Mevalonic acid-5-pyrophosphate
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.5477    1.9520    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862    0.4917    0.3836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5950   -0.0379    1.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.2859   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -0.2890   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.8262    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -0.7329   -0.1667 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5955    0.3559   -1.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -2.2488   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -0.4379    1.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7940    0.1015    0.6675 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.7913    0.1496    1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    1.6274   -0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2521   -0.9582   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    0.5061    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0861   -0.8262    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -1.8375    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4732   -1.0071    0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    2.1252   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    2.2768    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    2.6231    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882   -0.9916    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    0.1957   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -1.3060   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -0.9547   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    0.6823   -1.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -2.2764   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    2.3440    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929   -1.8112   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468    0.8807   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    1.2167    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -0.7010   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  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
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-5                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      -4.565   2.592   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0      -4.565   1.052   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      -4.565  -0.488   0.000  0.00  0.00           O+0
HETATM    4  P   UNK     0      -3.231  -1.258   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      -1.897  -2.028   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.564  -1.258   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770  -2.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.437  -2.028   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.771  -1.258   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.105  -2.028   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.025   1.052   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -6.105   1.052   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.461   0.076   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001  -2.592   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.094  -0.078   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.114  -0.078   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.771   0.282   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16   17                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    2                                                            
CONECT   14    4                                                            
CONECT   15    4                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18   10                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0001981
HETATM    1  C1  UNL     1      -1.548   1.952   0.286  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.986   0.492   0.384  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.595  -0.038   1.600  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.466  -0.286  -0.793  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.026  -0.289  -0.908  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.686  -0.826   0.167  1.00  0.00           O  
HETATM    7  P1  UNL     1       2.343  -0.733  -0.167  1.00  0.00           P  
HETATM    8  O3  UNL     1       2.595   0.356  -1.169  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.817  -2.249  -0.780  1.00  0.00           O  
HETATM   10  O5  UNL     1       3.263  -0.438   1.203  1.00  0.00           O  
HETATM   11  P2  UNL     1       4.794   0.102   0.667  1.00  0.00           P  
HETATM   12  O6  UNL     1       5.791   0.150   1.776  1.00  0.00           O  
HETATM   13  O7  UNL     1       4.590   1.627  -0.047  1.00  0.00           O  
HETATM   14  O8  UNL     1       5.252  -0.958  -0.580  1.00  0.00           O  
HETATM   15  C5  UNL     1      -3.490   0.506   0.321  1.00  0.00           C  
HETATM   16  C6  UNL     1      -4.086  -0.826   0.443  1.00  0.00           C  
HETATM   17  O9  UNL     1      -3.407  -1.837   0.691  1.00  0.00           O  
HETATM   18  O10 UNL     1      -5.473  -1.007   0.282  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.728   2.125  -0.405  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.220   2.277   1.296  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.383   2.623   0.003  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.388  -0.992   1.551  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.876   0.196  -1.707  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.840  -1.306  -0.772  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.263  -0.955  -1.790  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.480   0.682  -1.169  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.560  -2.276  -1.744  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.946   2.344   0.520  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.593  -1.811  -0.252  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.747   0.881  -0.708  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.930   1.217   1.063  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.835  -0.701  -0.614  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   15
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   27
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   28
CONECT   14   29
CONECT   15   16   30   31
CONECT   16   17   17   18
CONECT   18   32
END

HMDB0001981
     RDKit          3D
(R)-Mevalonic acid-5-pyrophosphate
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.5477    1.9520    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862    0.4917    0.3836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5950   -0.0379    1.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.2859   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260   -0.2890   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.8262    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -0.7329   -0.1667 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5955    0.3559   -1.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -2.2488   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -0.4379    1.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7940    0.1015    0.6675 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.7913    0.1496    1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    1.6274   -0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2521   -0.9582   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    0.5061    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0861   -0.8262    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -1.8375    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4732   -1.0071    0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    2.1252   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    2.2768    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    2.6231    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882   -0.9916    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    0.1957   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -1.3060   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -0.9547   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    0.6823   -1.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -2.2764   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    2.3440    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929   -1.8112   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468    0.8807   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    1.2167    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8353   -0.7010   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  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
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Mevalonate-5-pyrophosphate	Generator
(R)-Mevalonic acid-5-pyrophosphoric acid	Generator
(R)-5-Diphosphomevalonic acid	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oate	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid 1,3-dioxide	HMDB
5-Pyrophosphomevalonate	HMDB
5-Pyrophosphomevalonic acid	HMDB
Mevalonate 5-diphosphate	HMDB
Mevalonic 5-pyrophosphate	HMDB
Mevalonic acid 5-diphosphate	HMDB
Mevalonic acid 5-pyrophosphate	HMDB
Mevalonic acid pyrophosphate	HMDB
MVADP	HMDB
Pyrophosphomevalonate	HMDB
Pyrophosphomevalonic acid	HMDB
R-Mevalonic acid-5-pyrophosphate	HMDB
Mevalonate pyrophosphate	MeSH, HMDB
5-Diphosphomevalonic acid	MeSH, HMDB
(3S)-3-Hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoate	Generator, HMDB

Chemical Formula

C₆H₁₄O₁₀P₂

Average Molecular Weight

308.1169

Monoisotopic Molecular Weight

308.006219692

IUPAC Name

(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid

Traditional Name

pyrophosphomevalonate

CAS Registry Number

1492-08-6

SMILES

C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m0/s1

InChI Key

SIGQQUBJQXSAMW-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic pyrophosphates

Direct Parent

Organic pyrophosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoalkyl phosphate
Short-chain hydroxy acid
Organic phosphoric acid derivative
Fatty acid
Alkyl phosphate
Phosphoric acid ester
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Leukocyte (HMDB: HMDB0001981)

Source

Endogenous

Endogenous (HMDB: HMDB0001981)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

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)

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)

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)

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)

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)

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)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

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

Bean

Green lentil (FooDB: FOOD00970)

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

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mevalonate Pathway (PathBank: SMP0121055)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	153.219	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001842

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.26 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	56.26 m³·mol⁻¹	ChemAxon
Polarizability	23.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.133	31661259
DarkChem	[M-H]-	160.018	31661259
AllCCS	[M+H]+	164.528	32859911
AllCCS	[M-H]-	156.982	32859911
DeepCCS	[M+H]+	148.447	30932474
DeepCCS	[M-H]-	146.459	30932474
DeepCCS	[M-2H]-	179.697	30932474
DeepCCS	[M+Na]+	154.36	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	161.5	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	157.7	32859911
AllCCS	[M+HCOO]-	158.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Mevalonic acid-5-pyrophosphate	C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	3795.9	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate	C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	1913.2	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate	C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	2474.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #1	C[C@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C	2475.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #2	C[C@](O)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O[Si](C)(C)C	2412.1	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #3	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O	2431.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #4	C[C@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O	2447.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #1	C[C@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2422.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #2	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C	2440.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #3	C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2464.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #4	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O[Si](C)(C)C	2366.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #5	C[C@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2376.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #6	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O	2408.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #7	C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2408.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2388.4	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2350.0	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3183.8	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2397.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2331.0	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3269.3	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2449.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2286.6	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	3048.5	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2443.9	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2276.7	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	3063.4	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2372.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2347.0	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	3055.7	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6	C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2384.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6	C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2334.3	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6	C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	3063.0	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2417.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2283.1	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2863.7	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2436.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2384.1	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2902.6	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2442.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2375.8	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2	C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2895.9	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2479.3	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2325.2	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2725.7	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2399.5	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2375.3	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4	C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2730.6	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2479.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2410.1	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1	C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2610.0	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O	2692.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O)O	2633.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O)O	2661.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)OCC[C@](C)(O)CC(=O)O	2674.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2839.5	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CC(=O)O	2857.4	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	2871.1	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2818.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2816.1	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(OCC[C@](C)(O)CC(=O)O)O[Si](C)(C)C(C)(C)C	2844.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[C@](C)(O)CC(=O)O	2848.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3035.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2829.4	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3384.9	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3036.5	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2827.0	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3459.6	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	3063.9	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	2774.6	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	3264.1	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3066.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	2733.7	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3283.7	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3010.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2840.1	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3268.6	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3020.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2792.7	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3279.8	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3025.6	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2738.4	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3099.1	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3220.0	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2964.6	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3175.1	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3225.8	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2930.6	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3184.8	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](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)C)CC(=O)O	3263.7	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](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)C)CC(=O)O	2869.6	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@](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)C)CC(=O)O	3027.3	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)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)C	3199.2	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)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)C	2926.5	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)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)C	3032.4	Standard polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](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)C)O[Si](C)(C)C(C)(C)C	3381.5	Semi standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](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)C)O[Si](C)(C)C(C)(C)C	3069.3	Standard non polar	33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@](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)C)O[Si](C)(C)C(C)(C)C	3015.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-9820000000-20a5a060549dcb7bd8d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate GC-MS (2 TMS) - 70eV, Positive	splash10-00dv-9243200000-6d8177d69adb810da37f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 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 - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 5V, negative-QTOF	splash10-000i-0090000000-27d85eaaa9c4e19f0fcf	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 6V, negative-QTOF	splash10-000i-0090000000-8e9a7018cd2663189521	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 9V, negative-QTOF	splash10-002r-3490000000-b2f4bcb965dfbe91ce8f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 11V, negative-QTOF	splash10-004r-7690000000-533cfa9b6449fe59e31d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 12V, negative-QTOF	splash10-004i-9540000000-ba3a429bcc345a49d5ff	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 15V, negative-QTOF	splash10-004i-9310000000-b552a514df86bf203483	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 18V, negative-QTOF	splash10-004i-9200000000-73f02610e11b09ea0ae0	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 20V, negative-QTOF	splash10-004i-9100000000-e99ccf8685bbb8c58b7f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 25V, negative-QTOF	splash10-004i-9000000000-df1600382f0903920e95	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-004i-1900000000-0d135499da95ac5499d5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-0a4i-0900000000-b559d4679fc0eaa79be7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-004i-1590000000-bd14b17224627a5d2418	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-0a4i-0900000000-dc954ce23ecf1a263189	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOF	splash10-0kdi-0490000000-356afce14b98128806e5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 5V, negative-QTOF	splash10-0a4i-0009000000-ece59023c1177bedb2f3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 7V, negative-QTOF	splash10-0a4i-0009000000-cbc9841391b1e5bea83c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 9V, negative-QTOF	splash10-0a4i-1109000000-71626d1a601d118a3d29	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 11V, negative-QTOF	splash10-0a6r-9516000000-b1e714407672ea74b65f	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 10V, Positive-QTOF	splash10-0006-1491000000-8b66d9021d8692cc58b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 20V, Positive-QTOF	splash10-03ea-5930000000-ed4d02286446a704e70d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 40V, Positive-QTOF	splash10-03ea-9810000000-99f0d148c2b3cc6b87e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 10V, Negative-QTOF	splash10-0bvi-0494000000-00b15359794ef7c74743	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 20V, Negative-QTOF	splash10-004i-9410000000-5d44f0388a33861701fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 40V, Negative-QTOF	splash10-004i-9000000000-b038a323df0665a33d9c	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Leukocyte

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022779

KNApSAcK ID

Not Available

Chemspider ID

17216150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6415

PubChem Compound

22833574

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bloch, Konrad; Chaykin, S.; Phillips, A. H.; De Waard, A. Mevalonic acid pyrophosphate and isopentylpyrophosphate. Journal of Biological Chemistry (1959), 234 2595-2604.

Material Safety Data Sheet (MSDS)

Not Available

General References

Cuthbert JA, Lipsky PE: Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. J Biol Chem. 1990 Oct 25;265(30):18568-75. [PubMed:2211719 ]
Ku EC: Regulation of fatty acid biosynthesis by intermediates of the cholesterol biosynthetic pathway. Biochem Biophys Res Commun. 1996 Aug 5;225(1):173-9. [PubMed:8769113 ]

Enzymes

Enzyme Details

1. Diphosphomevalonate decarboxylase

General function:: Involved in ATP binding
Specific function:: Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:: MVD
Uniprot ID:: P53602
Molecular weight:: 43404.125

Enzyme Details

2. Phosphomevalonate kinase

General function:: Involved in phosphomevalonate kinase activity
Specific function:: Not Available
Gene Name:: PMVK
Uniprot ID:: Q15126
Molecular weight:: 21994.745

Showing metabocard for (R)-Mevalonic acid-5-pyrophosphate (HMDB0001981)

MOL for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

3D MOL for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

3D SDF for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

3D-SDF for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

PDB for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

3D PDB for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

SMILES for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

INCHI for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

Structure for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

3D Structure for HMDB0001981 ((R)-Mevalonic acid-5-pyrophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes