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Showing metabocard for Mevalonic acid-5P (HMDB0001343)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001343
Secondary Accession Numbers
  • HMDB01343
Metabolite Identification
Common NameMevalonic acid-5P
DescriptionMevalonic acid-5P (CAS: 1189-94-2), also known as 5-phosphomevalonic acid, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Within humans, mevalonic acid-5P participates in many enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonate; which is mediated by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into mevalonic acid-5-pyrophosphate through its interaction with the enzyme phosphomevalonate kinase. In humans, mevalonic acid-5P is involved in the mevalonate pathway. Outside of the human body, mevalonic acid-5P has been detected, but not quantified in, several different foods, such as oriental wheat, devilfish, pepper (spice), redcurrants, and star fruits. This could make mevalonic acid-5P a potential biomarker for the consumption of these foods.
Structure
Data?1593186954
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001343 (Mevalonic acid-5P)


  Mrv1652306262017552D          

 14 13  0  0  0  0            999 V2000
 9979.8578 9977.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.1447 9978.2267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9980.5729 9978.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.4295 9977.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.5569 9978.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7325 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.2860 9977.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.5729 9979.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.7153 9978.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.0007 9977.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.2865 9978.2267    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9976.6980 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9975.5680 9977.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9975.8730 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  6  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
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3D MOL for HMDB0001343 (Mevalonic acid-5P)

HMDB0001343
     RDKit          3D
Mevalonic acid-5P
 27 26  0  0  0  0  0  0  0  0999 V2000
   -2.1416   -1.4280    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.4074    0.0047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1837    0.5938    1.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -0.7253   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602   -0.8907    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089   -1.2407   -0.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -0.1242   -0.2291 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3969    0.6343   -1.6770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0053   -0.7103   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549    1.0747    0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805    0.3803   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1032    1.1773   -0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078    0.6319   -0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.5516   -0.3074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -0.9722    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -2.0330   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106   -2.1176    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    0.9758    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6118   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    0.0839   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -1.7407    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.0786    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5256   -0.2915   -1.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437    1.9606    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2157    1.1932   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -0.1035   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    3.0609   -0.4369 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
  2 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 14 27  1  0
M  END
Download

3D SDF for HMDB0001343 (Mevalonic acid-5P)


  Mrv1652306262017552D          

 14 13  0  0  0  0            999 V2000
 9979.8578 9977.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.1447 9978.2267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9980.5729 9978.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.4295 9977.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.5569 9978.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7325 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.2860 9977.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.5729 9979.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.7153 9978.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.0007 9977.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.2865 9978.2267    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9976.6980 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9975.5680 9977.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9975.8730 9978.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  6  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001343

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1

> <INCHI_KEY>
OKZYCXHTTZZYSK-ZCFIWIBFSA-N

> <FORMULA>
C6H13O7P

> <MOLECULAR_WEIGHT>
228.137

> <EXACT_MASS>
228.039889282

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.23312112151381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-1.2169455899999997

> <ALOGPS_LOGS>
-1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.266040498026587

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.710901289606094

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9236237745946774

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
45.384299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mevalonate-5-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001343 (Mevalonic acid-5P)

HMDB0001343
     RDKit          3D
Mevalonic acid-5P
 27 26  0  0  0  0  0  0  0  0999 V2000
   -2.1416   -1.4280    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.4074    0.0047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1837    0.5938    1.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -0.7253   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602   -0.8907    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089   -1.2407   -0.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -0.1242   -0.2291 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3969    0.6343   -1.6770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0053   -0.7103   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549    1.0747    0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805    0.3803   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1032    1.1773   -0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078    0.6319   -0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.5516   -0.3074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -0.9722    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -2.0330   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106   -2.1176    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    0.9758    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6118   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    0.0839   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -1.7407    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.0786    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5256   -0.2915   -1.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437    1.9606    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2157    1.1932   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -0.1035   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    3.0609   -0.4369 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
  2 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 14 27  1  0
M  END
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PDB for HMDB0001343 (Mevalonic acid-5P)

HEADER    PROTEIN                                 26-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-JUN-20         0                                  
HETATM    1  C   UNK     0    8629.0688625.255   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8627.7378626.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8630.4038626.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8626.4028625.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8628.5068627.361   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8626.9678627.361   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8631.7348625.255   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8630.4038627.561   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8625.0698626.023   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8623.7358625.255   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0    8622.4018626.023   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0    8623.1708627.361   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8621.0608625.251   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8621.6308627.361   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7    8                                                  
CONECT    4    2    9                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for HMDB0001343 (Mevalonic acid-5P)

COMPND    HMDB0001343
HETATM    1  C1  UNL     1      -2.142  -1.428   0.701  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.312  -0.407   0.005  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.184   0.594   1.125  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.039  -0.725  -0.427  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.160  -0.891   0.546  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.209  -1.241  -0.367  1.00  0.00           O  
HETATM    7  P1  UNL     1       3.463  -0.124  -0.229  1.00  0.00           P  
HETATM    8  O3  UNL     1       3.397   0.634  -1.677  1.00  0.00           O  
HETATM    9  O4  UNL     1       5.005  -0.710  -0.220  1.00  0.00           O  
HETATM   10  O5  UNL     1       3.155   1.075   0.886  1.00  0.00           O  
HETATM   11  C5  UNL     1      -1.981   0.380  -1.049  1.00  0.00           C  
HETATM   12  C6  UNL     1      -3.103   1.177  -0.555  1.00  0.00           C  
HETATM   13  O6  UNL     1      -4.208   0.632  -0.273  1.00  0.00           O  
HETATM   14  O7  UNL     1      -3.061   2.552  -0.307  1.00  0.00           O  
HETATM   15  H1  UNL     1      -2.948  -0.972   1.281  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.704  -2.033  -0.089  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.511  -2.118   1.290  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.341   0.976   1.061  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.047  -1.612  -1.102  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.420   0.084  -1.171  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.941  -1.741   1.191  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.405   0.079   1.012  1.00  0.00           H  
HETATM   23  H9  UNL     1       5.526  -0.292  -1.001  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.344   1.961   0.489  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.216   1.193  -1.409  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.219  -0.104  -2.003  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.182   3.061  -0.437  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   11
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   23
CONECT   10   24
CONECT   11   12   25   26
CONECT   12   13   13   14
CONECT   14   27
END
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SMILES for HMDB0001343 (Mevalonic acid-5P)

C[C@@](O)(CCOP(O)(O)=O)CC(O)=O
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INCHI for HMDB0001343 (Mevalonic acid-5P)

InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(R)-5-PhosphomevalonateChEBI
(R)-5-Phosphomevaloonic acidChEBI
(R)-Mevalonic acid 5-phosphateChEBI
(R)-5-Phosphomevalonic acidGenerator
(R)-5-PhosphomevaloonateGenerator
(R)-Mevalonate 5-phosphateGenerator
(R)-Mevalonic acid 5-phosphoric acidGenerator
Mevalonate-5PGenerator
5-PhosphomevalonateHMDB
Mevalonate-5-pHMDB
Mevalonate-5-phosphateHMDB
Mevalonate-pHMDB
p-MevalonateHMDB
5-Phosphomevalonic acidHMDB
Mevalonate 5-phosphateHMDB
PhosphomevalonateHMDB
Phosphomevalonic acidHMDB
Phosphomevalonic acid, (+-)-isomerHMDB
(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
Mevalonic acid phosphateHMDB
Mevalonic acid-5PHMDB
Chemical FormulaC6H13O7P
Average Molecular Weight228.137
Monoisotopic Molecular Weight228.039889282
IUPAC Name(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
Traditional Namemevalonate-5-phosphate
CAS Registry Number73566-35-5
SMILES
C[C@@](O)(CCOP(O)(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1
InChI KeyOKZYCXHTTZZYSK-ZCFIWIBFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Fatty acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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 Available140.015http://allccs.zhulab.cn/database/detail?ID=AllCCS00001771
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.9 g/LALOGPS
logP-2.2ALOGPS
logP-1.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.38 m³·mol⁻¹ChemAxon
Polarizability19.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.3231661259
DarkChem[M-H]-144.43631661259
AllCCS[M+H]+149.71132859911
AllCCS[M-H]-144.05432859911
DeepCCS[M+H]+135.29630932474
DeepCCS[M-H]-132.92230932474
DeepCCS[M-2H]-168.23730932474
DeepCCS[M+Na]+142.69630932474
AllCCS[M+H]+149.732859911
AllCCS[M+H-H2O]+146.232859911
AllCCS[M+NH4]+153.032859911
AllCCS[M+Na]+153.932859911
AllCCS[M-H]-144.132859911
AllCCS[M+Na-2H]-145.232859911
AllCCS[M+HCOO]-146.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.75 minutes32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.4 minutes32390414
Predicted by Siyang on May 30, 20229.3311 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.93 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid387.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid495.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid271.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid51.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid157.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid40.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid264.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid247.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)653.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid575.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid40.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid642.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid157.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid217.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate614.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA300.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water513.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Mevalonic acid-5PC[C@@](O)(CCOP(O)(O)=O)CC(O)=O2974.6Standard polar33892256
Mevalonic acid-5PC[C@@](O)(CCOP(O)(O)=O)CC(O)=O1557.5Standard non polar33892256
Mevalonic acid-5PC[C@@](O)(CCOP(O)(O)=O)CC(O)=O1938.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mevalonic acid-5P,1TMS,isomer #1C[C@@](CCOP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C1998.4Semi standard non polar33892256
Mevalonic acid-5P,1TMS,isomer #2C[C@@](O)(CCOP(=O)(O)O)CC(=O)O[Si](C)(C)C1934.0Semi standard non polar33892256
Mevalonic acid-5P,1TMS,isomer #3C[C@@](O)(CCOP(=O)(O)O[Si](C)(C)C)CC(=O)O1964.2Semi standard non polar33892256
Mevalonic acid-5P,2TMS,isomer #1C[C@@](CCOP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1991.2Semi standard non polar33892256
Mevalonic acid-5P,2TMS,isomer #2C[C@@](CCOP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2020.3Semi standard non polar33892256
Mevalonic acid-5P,2TMS,isomer #3C[C@@](O)(CCOP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C1958.1Semi standard non polar33892256
Mevalonic acid-5P,2TMS,isomer #4C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O1996.5Semi standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #1C[C@@](CCOP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2009.4Semi standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #1C[C@@](CCOP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1956.0Standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #1C[C@@](CCOP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2356.8Standard polar33892256
Mevalonic acid-5P,3TMS,isomer #2C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2053.5Semi standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #2C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C1890.7Standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #2C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2192.4Standard polar33892256
Mevalonic acid-5P,3TMS,isomer #3C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C1994.3Semi standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #3C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C1933.4Standard non polar33892256
Mevalonic acid-5P,3TMS,isomer #3C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2191.5Standard polar33892256
Mevalonic acid-5P,4TMS,isomer #1C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2055.9Semi standard non polar33892256
Mevalonic acid-5P,4TMS,isomer #1C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2000.0Standard non polar33892256
Mevalonic acid-5P,4TMS,isomer #1C[C@@](CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2095.7Standard polar33892256
Mevalonic acid-5P,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)O)CC(=O)O2225.1Semi standard non polar33892256
Mevalonic acid-5P,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)O2167.2Semi standard non polar33892256
Mevalonic acid-5P,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[C@@](C)(O)CC(=O)O2188.6Semi standard non polar33892256
Mevalonic acid-5P,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)O)O[Si](C)(C)C(C)(C)C2415.7Semi standard non polar33892256
Mevalonic acid-5P,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O2433.5Semi standard non polar33892256
Mevalonic acid-5P,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)O[Si](C)(C)C(C)(C)C2391.7Semi standard non polar33892256
Mevalonic acid-5P,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@@](C)(O)CC(=O)O)O[Si](C)(C)C(C)(C)C2431.5Semi standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2641.3Semi standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2533.0Standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2591.3Standard polar33892256
Mevalonic acid-5P,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O2666.0Semi standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O2420.8Standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O2486.2Standard polar33892256
Mevalonic acid-5P,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2617.8Semi standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2468.8Standard non polar33892256
Mevalonic acid-5P,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2489.4Standard polar33892256
Mevalonic acid-5P,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2854.2Semi standard non polar33892256
Mevalonic acid-5P,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2644.5Standard non polar33892256
Mevalonic acid-5P,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2475.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid-5P GC-MS (Non-derivatized) - 70eV, Positivesplash10-0292-9600000000-a4f04a66624afb8d522a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid-5P GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9413000000-7329637530b2ddc29e0b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid-5P GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 10V, Positive-QTOFsplash10-03di-1960000000-a02358583ea07452bacf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 20V, Positive-QTOFsplash10-03e9-4900000000-ef07c3371552f7c1c11d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 40V, Positive-QTOFsplash10-02ti-9800000000-bba2c1c56648b04a1fdd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 10V, Negative-QTOFsplash10-004i-8960000000-de18bb77f2282c89d45a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 20V, Negative-QTOFsplash10-004i-9100000000-6dd83d59bdb427eeee242016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 40V, Negative-QTOFsplash10-004i-9000000000-9c715a4954dce4d5a8562016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 10V, Positive-QTOFsplash10-01si-1940000000-c405e8487510c01d67be2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 20V, Positive-QTOFsplash10-0229-9300000000-84bcd8640d320dd874e32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 40V, Positive-QTOFsplash10-06ry-9200000000-6589ef1abdd6045116392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 10V, Negative-QTOFsplash10-004i-5090000000-98125cefd75fccd3e5642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 20V, Negative-QTOFsplash10-004i-9020000000-74f440cb4e3ffa40388d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid-5P 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Heart
  • Kidney
  • Liver
  • Pancreas
  • Skeletal Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031001
KNApSAcK IDC00007304
Chemspider ID388517
KEGG Compound IDC01107
BioCyc IDCPD-499
BiGG ID36819
Wikipedia LinkNot Available
METLIN ID6177
PubChem Compound439400
PDB IDNot Available
ChEBI ID17436
Food Biomarker OntologyNot Available
VMH ID5PMEV
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Popjak G, Boehm G, Parker TS, Edmond J, Edwards PA, Fogelman AM: Determination of mevalonate in blood plasma in man and rat. Mevalonate "tolerance" tests in man. J Lipid Res. 1979 Aug;20(6):716-28. [PubMed:226640 ]
  2. Campos N, Rodriguez-Concepcion M, Sauret-Gueto S, Gallego F, Lois LM, Boronat A: Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate: a novel system for the genetic analysis of the 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis. Biochem J. 2001 Jan 1;353(Pt 1):59-67. [PubMed:11115399 ]
  3. Houten SM, Waterham HR: Nonorthologous gene displacement of phosphomevalonate kinase. Mol Genet Metab. 2001 Mar;72(3):273-6. [PubMed:11243736 ]

Enzymes

Enzyme Details
1. Phosphomevalonate kinase
General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745
Reactions
Adenosine triphosphate + Mevalonic acid-5P → ADP + (R)-5-Diphosphomevalonic aciddetails
Enzyme Details
2. Mevalonate kinase
General function:
Involved in ATP binding
Specific function:
May be a regulatory site in cholesterol biosynthetic pathway.
Gene Name:
MVK
Uniprot ID:
Q03426
Molecular weight:
42450.475
Reactions
Adenosine triphosphate + Mevalonic acid → ADP + Mevalonic acid-5Pdetails