Showing metabocard for Mevalonic acid-5P (MMDBc0032937)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:28:04 UTC
Update Date2024-04-30 19:55:20 UTC
Metabolite IDMMDBc0032937
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923048a598>


  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
Download

3D MOL for #<Metabolite:0x00007f923048a598>

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 #<Metabolite:0x00007f923048a598>


  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>
MMDBc0032937

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f923048a598>

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 #<Metabolite:0x00007f923048a598>

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 #<Metabolite:0x00007f923048a598>

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 #<Metabolite:0x00007f923048a598>

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

INCHI for #<Metabolite:0x00007f923048a598>

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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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
Molecular FormulaC6H13O7P
Average Mass228.137
Monoisotopic Mass228.039889282
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