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Showing NP-Card for Mevalonic acid (NP0000114)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-15 04:56:45 UTC
NP-MRD IDNP0000114
Secondary Accession NumbersNone
Natural Product Identification
Common NameMevalonic acid
DescriptionMevalonic acid, also known as MVA, mevalonate, or hiochic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Mevalonic acid is a key organic compound in biochemistry. It is found in most higher organisms ranging from plants to animals. Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes (in plants) and steroids (in animals). Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. The production of mevalonic acid by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol (PMID: 12872277 ). The cholesterol biosynthetic pathway has three major steps: (1) Acetate to mevalonate, (2) mevalonate to squalene, and (3) squalene to cholesterol. In the first step, which catalyzed by thiolase, two acetyl-CoA molecules form acetoacetyl-CoA and one CoA molecule is released, then the acetoacetyl-CoA reacts with another molecule of acetyl-CoA and generates 3-hydroxy-3-methylglutaryl-CoA (HMGCoA). The enzyme responsible for this reaction is 3-hydroxy-3-methylglutaryl-CoA synthase (HMG-CoA synthase): In the pathway to synthesize cholesterol, one of the HMG-CoA carboxyl groups undergoes reduction to an alcohol, releasing CoA, leading to the formation of mevalonate, a six carbon compound. This reaction is catalyzed by hydroxy-methylglutaryl-CoA reductase, In the second step (mevalonate to squalene) mevalonate receives a phosphoryl group from ATP to form 5-phosphomevalonate. This compound accepts another phosphate to generate mevalonate-5-pyrophosphate. After a third phosphorylation, the compound is decarboxylated, loses water, and generates isopentenyl pyrophosphate (IPP). Then through successive condensations, IPP forms squalene, a terpene hydrocarbon that contains 30 carbon atoms. By cyclization and other changes, this compound will finally result in cholesterol. Mevalonic acid is found, on average, in the highest concentration within a few different foods, such as apples, corns, and wild carrots and in a lower concentration in garden tomato (var.), Pepper (C. Frutescens), and cucumbers. Mevalonic acid has also been detected, but not quantified in, several different foods, such as sweet oranges, potato, milk (cow), cabbages, and white cabbages. This could make mevalonic acid a potential biomarker for the consumption of these foods. Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin, and atorvastatin (PMID: 8808497 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000114 (Mevalonic acid)


  Mrv1652304242019462D          

 10  9  0  0  0  0            999 V2000
   -0.7155   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -0.2069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7141   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129    0.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    0.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for NP0000114 (Mevalonic acid)

HMDB0000227
     RDKit          3D
Mevalonic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -0.7391   -2.0908    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -0.6033    0.3783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0142   -0.4487    1.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -0.6459   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9245    0.5624   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.0384    0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952    0.2265   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693    1.6760   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179    2.3698    0.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215    2.4451   -0.9162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -2.1319   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -2.3047    1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -2.7774    0.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    0.3254    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9963   -1.0570   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6996   -1.4369    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    0.1993   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346    1.3530   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    1.4036    0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -0.0260    0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.1470   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766    2.0703   -0.9662 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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
M  END
Download

3D SDF for NP0000114 (Mevalonic acid)


  Mrv1652304242019462D          

 10  9  0  0  0  0            999 V2000
   -0.7155   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -0.2069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7141   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129    0.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    0.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000114

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1

> <INCHI_KEY>
KJTLQQUUPVSXIM-ZCFIWIBFSA-N

> <FORMULA>
C6H12O4

> <MOLECULAR_WEIGHT>
148.1571

> <EXACT_MASS>
148.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.570780322838882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3,5-dihydroxy-3-methylpentanoic acid

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-1.0933795586666666

> <ALOGPS_LOGS>
0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.950224499840974

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3846810662930205

> <JCHEM_PKA_STRONGEST_BASIC>
-2.413404454395632

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
34.5114

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mevalonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000114 (Mevalonic acid)

HMDB0000227
     RDKit          3D
Mevalonic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -0.7391   -2.0908    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -0.6033    0.3783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0142   -0.4487    1.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -0.6459   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9245    0.5624   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.0384    0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952    0.2265   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693    1.6760   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3179    2.3698    0.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215    2.4451   -0.9162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -2.1319   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -2.3047    1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -2.7774    0.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    0.3254    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9963   -1.0570   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6996   -1.4369    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    0.1993   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346    1.3530   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    1.4036    0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -0.0260    0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.1470   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766    2.0703   -0.9662 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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
M  END
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PDB for NP0000114 (Mevalonic acid)

HEADER    PROTEIN                                 24-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-20         0                                  
HETATM    1  C   UNK     0      -1.336  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.001  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.333  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.673  -0.386   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.005  -1.155   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.771   0.951   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.770   0.951   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.670  -0.386   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.005  -1.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.670   1.155   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000114 (Mevalonic acid)

COMPND    HMDB0000227
HETATM    1  C1  UNL     1      -0.739  -2.091   0.213  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.216  -0.603   0.378  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.014  -0.449   1.726  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.083  -0.646  -0.340  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.924   0.562  -0.402  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.330   1.038   0.865  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.295   0.226  -0.222  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.169   1.676  -0.194  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.318   2.370   0.390  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.122   2.445  -0.916  1.00  0.00           O  
HETATM   11  H1  UNL     1      -1.250  -2.132  -0.749  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.455  -2.305   1.017  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.107  -2.777   0.229  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.505   0.325   2.051  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.996  -1.057  -1.374  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.700  -1.437   0.200  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.926   0.199  -0.842  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.635   1.353  -1.090  1.00  0.00           H  
HETATM   19  H9  UNL     1       3.254   1.404   0.844  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.270  -0.026   0.315  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.526  -0.147  -1.274  1.00  0.00           H  
HETATM   22  H12 UNL     1      -3.077   2.070  -0.966  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4    7
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6   19
CONECT    7    8   20   21
CONECT    8    9    9   10
CONECT   10   22
END
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SMILES for NP0000114 (Mevalonic acid)

C[C@@](O)(CCO)CC(O)=O
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INCHI for NP0000114 (Mevalonic acid)

InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
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View in JSmol
Synonyms
ValueSource
(R)-3,5-Dihydroxy-3-methylvaleric acidChEBI
(R)-MevalonateChEBI
3,5-Dihydroxy-3-methylvaleric acidChEBI
(R)-3,5-Dihydroxy-3-methylvalerateGenerator
(R)-Mevalonic acidGenerator
3,5-Dihydroxy-3-methylvalerateGenerator
MevalonateGenerator
Acid, mevalonicHMDB
(3R)-3,5-Dihydroxy-3-methylpentanoic acidHMDB
(3R)-Mevalonic acidHMDB
(R)-(-)-Mevalonic acidHMDB
(R)-3,5-Dihydroxy-3-methylpentanoic acidHMDB
2,4-Dideoxy-3-C-methylpentonic acidHMDB
3,5-Dihydroxy-3-methylpentanoic acidHMDB
Hiochic acidHMDB
MVAHMDB
R-Mevalonic acidHMDB
beta,delta-Dihydroxy-beta-methylvaleric acidHMDB
Β,δ-dihydroxy-β-methylvaleric acidHMDB
Mevalonic acidChEBI
Chemical FormulaC6H12O4
Average Mass148.1571 Da
Monoisotopic Mass148.07356 Da
IUPAC Name(3R)-3,5-dihydroxy-3-methylpentanoic acid
Traditional Namemevalonic acid
CAS Registry Number150-97-0
SMILES
CC(O)(CCO)CC(O)=O
InChI Identifier
InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)
InChI KeyKJTLQQUUPVSXIM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaKNApSAcK Database
Asparagus officinalisKNApSAcK Database
Aspergillus oryzaeLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. capitataFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuum var. annuumFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clausena lansiumKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Cucumis sativus L.FooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Gentiana stramineaKNApSAcK Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Matricaria recutitaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Momordica charantiaKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pisum sativumFooDB
Polygonum minusKNApSAcK Database
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point24 - 27 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/Mevalonic-acid#section=Color-Form
Boiling PointNot AvailableNot Available
Water Solubility6 mg/mLhttps://pubchem.ncbi.nlm.nih.gov/source/hsdb/7681#section=LogP
LogP-0.58https://pubchem.ncbi.nlm.nih.gov/compound/Mevalonic-acid#section=LogP
Predicted Properties
PropertyValueSource
Water Solubility414 g/LALOGPS
logP-0.9ALOGPS
logP-1.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.51 m³·mol⁻¹ChemAxon
Polarizability14.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000227
DrugBank IDDB03518
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005126
KNApSAcK IDC00001195
Chemspider ID388367
KEGG Compound IDC00418
BioCyc IDMEVALONATE
BiGG IDNot Available
Wikipedia LinkMevalonic_acid
METLIN IDNot Available
PubChem Compound439230
PDB IDNot Available
ChEBI ID17710
Good Scents IDNot Available
References
General References
  1. Houten SM, Kuis W, Duran M, de Koning TJ, van Royen-Kerkhof A, Romeijn GJ, Frenkel J, Dorland L, de Barse MM, Huijbers WA, Rijkers GT, Waterham HR, Wanders RJ, Poll-The BT: Mutations in MVK, encoding mevalonate kinase, cause hyperimmunoglobulinaemia D and periodic fever syndrome. Nat Genet. 1999 Jun;22(2):175-7. [PubMed:10369261 ]
  2. Hoffmann G, Gibson KM, Brandt IK, Bader PI, Wappner RS, Sweetman L: Mevalonic aciduria--an inborn error of cholesterol and nonsterol isoprene biosynthesis. N Engl J Med. 1986 Jun 19;314(25):1610-4. [PubMed:3012338 ]
  3. Dmitrieva NA, Perrun'kina AM, Khomulo PS: [Determination of mevalonic acid in the urine and its concentration in the urine of patients with atherosclerosis]. Vopr Med Khim. 1968 Jan-Feb;14(1):106-8. [PubMed:5683362 ]
  4. Larson RA, Chung J, Scanu AM, Yachnin S: Neutrophils are required for the DNA synthetic response of human lymphocytes to mevalonic acid: evidence suggesting that a nonsterol product of mevalonate is involved. Proc Natl Acad Sci U S A. 1982 May;79(9):3028-32. [PubMed:6953445 ]
  5. Siavoshian S, Simoneau C, Maugeais P, Marks L, Rodary L, Gardette J, Krempf M: Measurement of mevalonic acid in human urine by bench top gas chromatography-mass spectrometry. Clin Chim Acta. 1995 Dec 29;243(2):129-36. [PubMed:8747489 ]
  6. Mitchell ED Jr, Avigan J: Control of phosphorylation and decarboxylation of mevalonic acid and its metabolites in cultured human fibroblasts and in rat liver in vivo. J Biol Chem. 1981 Jun 25;256(12):6170-3. [PubMed:6263908 ]
  7. Abrar M, Martin PD: Validation and application of an assay for the determination of mevalonic acid in human plasma by liquid chromatography tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jun 25;773(2):103-11. [PubMed:12031835 ]
  8. Haas D, Kelley RI, Hoffmann GF: Inherited disorders of cholesterol biosynthesis. Neuropediatrics. 2001 Jun;32(3):113-22. [PubMed:11521206 ]
  9. Larson RA, Kluskens LE, Yachnin S: The DNA synthetic response of normal and abnormal human lymphocytes to mevalonic acid: the role of granulocytes as a helper population. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 1):280-90. [PubMed:6236250 ]
  10. Larson RA, Yachnin S: Mevalonic acid induces DNA synthesis in chronic lymphocytic leukemia cells. Blood. 1984 Jul;64(1):257-62. [PubMed:6610447 ]
  11. Parker TS, McNamara DJ, Brown CD, Kolb R, Ahrens EH Jr, Alberts AW, Tobert J, Chen J, De Schepper PJ: Plasma mevalonate as a measure of cholesterol synthesis in man. J Clin Invest. 1984 Sep;74(3):795-804. [PubMed:6565710 ]
  12. Hoffmann GF, Sweetman L, Bremer HJ, Hunneman DH, Hyanek J, Kozich V, Lehnert W, Nyhan WL, Speidel I, Trefz FK, et al.: Facts and artefacts in mevalonic aciduria: development of a stable isotope dilution GCMS assay for mevalonic acid and its application to physiological fluids, tissue samples, prenatal diagnosis and carrier detection. Clin Chim Acta. 1991 May 15;198(3):209-27. [PubMed:1653652 ]
  13. Jemal M, Schuster A, Whigan DB: Liquid chromatography/tandem mass spectrometry methods for quantitation of mevalonic acid in human plasma and urine: method validation, demonstration of using a surrogate analyte, and demonstration of unacceptable matrix effect in spite of use of a stable isotope analog internal standard. Rapid Commun Mass Spectrom. 2003;17(15):1723-34. [PubMed:12872277 ]
  14. Lindenthal B, von Bergmann K: Urinary excretion and serum concentration of mevalonic acid during acute intake of alcohol. Metabolism. 2000 Jan;49(1):62-6. [PubMed:10647065 ]
  15. Naoumova RP, Marais AD, Mountney J, Firth JC, Rendell NB, Taylor GW, Thompson GR: Plasma mevalonic acid, an index of cholesterol synthesis in vivo, and responsiveness to HMG-CoA reductase inhibitors in familial hypercholesterolaemia. Atherosclerosis. 1996 Jan 26;119(2):203-13. doi: 10.1016/0021-9150(95)05649-1. [PubMed:8808497 ]