MiMeDB: Showing metabocard for Ubiquinone Q1 (MMDBc0032915)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:27:13 UTC

Update Date

2024-04-30 19:54:57 UTC

Metabolite ID

MMDBc0032915

Metabolite Identification

Common Name

Ubiquinone Q1

Description

Ubiquinone-1 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-1 has just 1 isoprene unit. Normally in humans it has 10. Ubiquinone-1 is an intermediate in the synthesis of Ubiquionone 10, which is also called Coenzyme Q (CoQ). CoQ is found in the membranes of endoplasmic reticulum, peroxisomes, lysosomes, vesicles and notably the inner membrane of the mitochondrion where it is an important part of the electron transport chain; there it passes reducing equivalents to acceptors such as Coenzyme Q : cytochrome c - oxidoreductase. CoQ is also essential in the formation of the apoptosome along with other adapter proteins. The loss of trophic factors activates pro-apoptotic enzymes, causing the breakdown of mitochondria. Because of its ability to transfer electrons and therefore act as an antioxidant, Coenzyme Q has become a valued dietary supplement. CoQ10 has been widely used for the treatment of heart disease (especially heart failure), gum diseases, and also breast cancer. The benzoquinone portion of Coenzyme Q10 is synthesized from amino acids, while the isoprene sidechain is synthesized from acetyl CoA through the mevalonate pathway. The mevalonate pathway is used for the first steps of cholesterol biosynthesis.

Structure

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

HMDB0002012
     RDKit          3D
Ubiquinone-1
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6627    1.1859   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246    0.1691    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2674    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    0.1556   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -0.0599   -1.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119   -1.3911   -2.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.2597   -0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    0.1465   -1.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    0.4861    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    0.5905    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -0.6541    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.6509   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    0.5899   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421   -1.9418   -0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981    0.5985    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.8242    3.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.4970    1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6031    2.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.9550   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281    1.2973   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    2.1657    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.0963   -2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -1.6638   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -1.4667   -3.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1162    1.4362    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7506    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -1.5825    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6589    0.3981   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.3501   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9949   -1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.7490   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0733   -2.5541    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2981   -2.4779   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918   -0.0779    3.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099    0.9403    3.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7372    1.7043    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 02231219192D          

 18 18  0  0  0  0            999 V2000
   16.1425   -7.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5716   -8.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1425   -5.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0005   -7.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5716   -5.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1425   -8.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2860   -8.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5716   -3.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0005   -3.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0005   -5.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2860   -3.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2860   -4.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8570   -6.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2860   -7.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8570   -7.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5716   -7.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5716   -5.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2860   -6.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  7  1  0  0  0  0
  2 16  1  0  0  0  0
  3 13  2  0  0  0  0
  4 14  2  0  0  0  0
  5 12  1  0  0  0  0
  5 17  1  0  0  0  0
  8 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  2  0  0  0  0
 13 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032915

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6H,7H2,1-5H3

> <INCHI_KEY>
SOECUQMRSRVZQQ-UHFFFAOYSA-N

> <FORMULA>
C14H18O4

> <MOLECULAR_WEIGHT>
250.2903

> <EXACT_MASS>
250.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.944539108013224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.218699816000001

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.718903579766058

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
72.3818

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ubiquinone-1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002012
     RDKit          3D
Ubiquinone-1
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6627    1.1859   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246    0.1691    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2674    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    0.1556   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -0.0599   -1.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119   -1.3911   -2.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.2597   -0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    0.1465   -1.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    0.4861    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    0.5905    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -0.6541    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.6509   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    0.5899   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421   -1.9418   -0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981    0.5985    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.8242    3.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.4970    1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6031    2.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.9550   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281    1.2973   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    2.1657    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.0963   -2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -1.6638   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -1.4667   -3.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1162    1.4362    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7506    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -1.5825    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6589    0.3981   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.3501   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9949   -1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.7490   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0733   -2.5541    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2981   -2.4779   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918   -0.0779    3.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099    0.9403    3.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7372    1.7043    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.133 -13.988   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      32.800 -15.528   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.133 -10.908   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.468 -13.988   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      32.800  -9.368   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.133 -15.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.134 -16.298   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.800  -6.288   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.468  -6.288   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.468 -10.908   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.134  -7.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.134  -8.598   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.466 -11.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.134 -13.218   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.466 -13.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.800 -13.988   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.800 -10.908   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.134 -11.678   0.000  0.00  0.00           C+0
CONECT    1    6   15                                                       
CONECT    2    7   16                                                       
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   12   17                                                       
CONECT    6    1                                                            
CONECT    7    2                                                            
CONECT    8   11                                                            
CONECT    9   11                                                            
CONECT   10   18                                                            
CONECT   11    8    9   12                                                  
CONECT   12    5   11                                                       
CONECT   13    3   15   17                                                  
CONECT   14    4   16   18                                                  
CONECT   15    1   13   16                                                  
CONECT   16    2   14   15                                                  
CONECT   17    5   13   18                                                  
CONECT   18   10   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0002012
HETATM    1  C1  UNL     1      -4.663   1.186  -0.481  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.925   0.169   0.188  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.560   0.267   0.340  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.770   0.156  -0.710  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.362  -0.060  -1.945  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.812  -1.391  -2.207  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.300   0.260  -0.558  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.413   0.147  -1.588  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.287   0.486   0.751  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.728   0.591   0.929  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.390  -0.654   0.472  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.308  -0.651  -0.468  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.759   0.590  -1.147  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.942  -1.942  -0.889  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.498   0.598   1.805  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.081   0.824   3.112  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.953   0.497   1.664  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.706   0.603   2.663  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.738   0.955  -0.517  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.228   1.297  -1.506  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.547   2.166   0.029  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.968  -2.096  -2.160  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.509  -1.664  -1.370  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.346  -1.467  -3.166  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.116   1.436   0.294  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.056   0.751   1.971  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.102  -1.582   0.932  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.659   0.398  -1.771  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.039   1.350  -0.362  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.000   0.995  -1.818  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.914  -1.749  -1.370  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.073  -2.554   0.027  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.298  -2.478  -1.614  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.692  -0.078   3.397  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.710   0.940   3.876  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.737   1.704   3.200  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5    7
CONECT    5    6
CONECT    6   22   23   24
CONECT    7    8    8    9
CONECT    9   10   15   15
CONECT   10   11   25   26
CONECT   11   12   12   27
CONECT   12   13   14
CONECT   13   28   29   30
CONECT   14   31   32   33
CONECT   15   16   17
CONECT   16   34   35   36
CONECT   17   18   18
END

HMDB0002012
     RDKit          3D
Ubiquinone-1
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6627    1.1859   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246    0.1691    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    0.2674    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    0.1556   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -0.0599   -1.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119   -1.3911   -2.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.2597   -0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    0.1465   -1.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866    0.4861    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278    0.5905    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -0.6541    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.6509   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    0.5899   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421   -1.9418   -0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981    0.5985    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.8242    3.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.4970    1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    0.6031    2.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.9550   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281    1.2973   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    2.1657    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -2.0963   -2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -1.6638   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463   -1.4667   -3.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1162    1.4362    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7506    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -1.5825    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6589    0.3981   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.3501   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9949   -1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.7490   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0733   -2.5541    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2981   -2.4779   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918   -0.0779    3.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099    0.9403    3.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7372    1.7043    3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

Synonyms

Value	Source
2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-2,5-cyclohexadiene-1,4-dione	ChEBI
2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)-1,4-benzoquinone	ChEBI
2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-enyl)benzo-1,4-quinone	ChEBI
Coenzyme Q1	ChEBI
Coenzyme Q5	ChEBI
CoQ1	ChEBI
Ubiquinone Q1	ChEBI
Ubiquinone-Q1	HMDB
Ubiquionone 1	HMDB
Ubiquinone 5	HMDB

Molecular Formula

C₁₄H₁₈O₄

Average Mass

250.2903

Monoisotopic Mass

250.120509064

IUPAC Name

2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

Traditional Name

ubiquinone-1

CAS Registry Number

727-81-1

SMILES

COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O

InChI Identifier

InChI=1S/C14H18O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6H,7H2,1-5H3

InChI Key

SOECUQMRSRVZQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinones

Alternative Parents

Substituents

Ubiquinone skeleton
Monoterpenoid
Monocyclic monoterpenoid
Quinone
P-benzoquinone
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ubiquinones (CHEBI:46234 )
a ubiquinone (CPD0-1118 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.22	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.38 m³·mol⁻¹	ChemAxon
Polarizability	26.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ri-6690000000-54c21ecf74c316617005	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0190000000-e28dd9a4e1e31fde0aaa	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0frt-4790000000-e9b4aa7330c158e93f74	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pw9-9400000000-984285464810c9d07a1a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0190000000-d560b9e909b6d771b748	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0890000000-173d3724196ddfd71b38	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001r-8940000000-6ddd0c7bdddc6aa7ff07	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0290000000-9e5c50e003ff846d2547	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udj-0790000000-8a23daff690e754ae6d3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-9510000000-3f25dec2fa15314807a9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-18320cb565cfb33802ea	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-0190000000-dc8c85f383835f5a9e04	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdm-5950000000-0fe5b45bd4eebb786711	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Brain
Fibroblasts
Intestine
Leukocyte
Liver
Neuron
Pancreas
Platelet
Prostate
Skeletal Muscle

Tissue Locations

Brain
Fibroblasts
Intestine
Leukocyte
Liver
Neuron
Pancreas
Platelet
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191788	NADH-ubiquinone oxidoreductase chain 1	Unknown	P03886	Homo sapiens
MMDBp0191789	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1	Enzyme	O75438	Homo sapiens
MMDBp0191791	NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial	Unknown	O75306	Homo sapiens
MMDBp0191792	Succinate dehydrogenase cytochrome b560 subunit, mitochondrial	Unknown	Q99643	Homo sapiens
MMDBp0191795	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 12	Enzyme	Q9UI09	Homo sapiens
MMDBp0191798	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 1	Enzyme	O15239	Homo sapiens
MMDBp0191799	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4-like 2	Enzyme	Q9NRX3	Homo sapiens
MMDBp0191800	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 3	Enzyme	O95167	Homo sapiens
MMDBp0191801	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 8	Enzyme	P51970	Homo sapiens
MMDBp0191802	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4	Enzyme	O00483	Homo sapiens
MMDBp0191803	NADH-ubiquinone oxidoreductase chain 4L	Unknown	P03901	Homo sapiens
MMDBp0191804	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 11	Enzyme	Q86Y39	Homo sapiens
MMDBp0191808	NADH dehydrogenase [ubiquinone] iron-sulfur protein 4, mitochondrial	Unknown	O43181	Homo sapiens
MMDBp0191810	NADH-ubiquinone oxidoreductase chain 5	Unknown	P03915	Homo sapiens
MMDBp0191811	NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial	Unknown	O75489	Homo sapiens
MMDBp0191812	NADH dehydrogenase [ubiquinone] iron-sulfur protein 5	Unknown	O43920	Homo sapiens
MMDBp0191813	NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial	Unknown	P19404	Homo sapiens
MMDBp0191815	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 10, mitochondrial	Unknown	O95299	Homo sapiens
MMDBp0191816	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 6	Enzyme	P56556	Homo sapiens
MMDBp0191820	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 4	Enzyme	O95168	Homo sapiens
MMDBp0191821	Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Unknown	P31040	Homo sapiens
MMDBp0191823	NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial	Unknown	O00217	Homo sapiens
MMDBp0191825	NADH-ubiquinone oxidoreductase chain 2	Unknown	P03891	Homo sapiens
MMDBp0191828	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 7	Enzyme	O95182	Homo sapiens
MMDBp0191830	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 2	Enzyme	O43678	Homo sapiens
MMDBp0191833	NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial	Unknown	P28331	Homo sapiens
MMDBp0191834	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 5, mitochondrial	Enzyme	O43674	Homo sapiens
MMDBp0191841	NADH dehydrogenase [ubiquinone] 1 subunit C2	Enzyme	O95298	Homo sapiens
MMDBp0191843	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 3	Enzyme	O43676	Homo sapiens
MMDBp0191844	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 7	Enzyme	P17568	Homo sapiens
MMDBp0191845	Acyl carrier protein, mitochondrial	Enzyme	O14561	Homo sapiens
MMDBp0191846	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 5	Enzyme	Q16718	Homo sapiens
MMDBp0191847	Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial	Unknown	Q16134	Homo sapiens
MMDBp0191848	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9, mitochondrial	Unknown	Q16795	Homo sapiens
MMDBp0191849	NADH-ubiquinone oxidoreductase chain 4	Unknown	P03905	Homo sapiens
MMDBp0191850	Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial	Unknown	O14521	Homo sapiens
MMDBp0191851	NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial	Unknown	O75251	Homo sapiens
MMDBp0191853	NADH-ubiquinone oxidoreductase chain 3	Unknown	P03897	Homo sapiens
MMDBp0191857	NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial	Unknown	P49821	Homo sapiens
MMDBp0191858	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 9	Enzyme	Q9Y6M9	Homo sapiens
MMDBp0191860	NADH-ubiquinone oxidoreductase chain 6	Unknown	P03923	Homo sapiens
MMDBp0191861	NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 13	Enzyme	Q9P0J0	Homo sapiens
MMDBp0191862	NADH dehydrogenase [ubiquinone] iron-sulfur protein 6, mitochondrial	Unknown	O75380	Homo sapiens
MMDBp0191864	Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Unknown	P21912	Homo sapiens
MMDBp0192083	Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial	Unknown	Q9NZJ6	Homo sapiens
MMDBp0192597	Cytochrome b-c1 complex subunit 2, mitochondrial	Unknown	P22695	Homo sapiens
MMDBp0192598	Cytochrome b-c1 complex subunit 9	Unknown	Q9UDW1	Homo sapiens
MMDBp0192599	Cytochrome b-c1 complex subunit 1, mitochondrial	Unknown	P31930	Homo sapiens
MMDBp0192600	Cytochrome b-c1 complex subunit 7	Enzyme	P14927	Homo sapiens
MMDBp0192602	Cytochrome b-c1 complex subunit Rieske, mitochondrial	Enzyme	P47985	Homo sapiens
MMDBp0192603	Cytochrome c1, heme protein, mitochondrial	Unknown	P08574	Homo sapiens
MMDBp0192604	Cytochrome b-c1 complex subunit 6, mitochondrial	Unknown	P07919	Homo sapiens
MMDBp0192712	NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 11, mitochondrial	Enzyme	Q9NX14	Homo sapiens
MMDBp0193481	Cytochrome b-c1 complex subunit 8	Enzyme	O14949	Homo sapiens
MMDBp0193819	Cytochrome b-c1 complex subunit 10	Unknown	O14957	Homo sapiens
MMDBp0196143	NADH dehydrogenase (Ubiquinone) 1 beta subcomplex, 2, 8kDa	Enzyme	A4D1T5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Multiple sclerosis	Decreased	Association	Human Blood	HMDB	10609336

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.00084	0.00040	uM	Adult (>18 years old)	Both	Multiple sclerosis	HMDB	10609336
Human Blood	Detected and Quantified	0.00312	0.00032	uM	Adult (>18 years old)	Both	Normal	HMDB	10609336
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0002012

DrugBank ID

DB08689

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022794

KNApSAcK ID

Not Available

Chemspider ID

4307

KEGG Compound ID

C00399

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6435

PubChem Compound

4462

PDB ID

Not Available

ChEBI ID

46234

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Edlund C, Soderberg M, Kristensson K, Dallner G: Ubiquinone, dolichol, and cholesterol metabolism in aging and Alzheimer's disease. Biochem Cell Biol. 1992 Jun;70(6):422-8. doi: 10.1139/o92-065. [PubMed:1449707 ]
Elmberger PG, Kalen A, Brunk UT, Dallner G: Discharge of newly-synthesized dolichol and ubiquinone with lipoproteins to rat liver perfusate and to the bile. Lipids. 1989 Nov;24(11):919-30. doi: 10.1007/BF02544535. [PubMed:2615561 ]
Laaksonen R, Jokelainen K, Sahi T, Tikkanen MJ, Himberg JJ: Decreases in serum ubiquinone concentrations do not result in reduced levels in muscle tissue during short-term simvastatin treatment in humans. Clin Pharmacol Ther. 1995 Jan;57(1):62-6. doi: 10.1016/0009-9236(95)90266-X. [PubMed:7828383 ]
Karlsson J, Lin L, Sylven C, Jansson E: Muscle ubiquinone in healthy physically active males. Mol Cell Biochem. 1996 Mar 23;156(2):169-72. doi: 10.1007/BF00426340. [PubMed:9095474 ]
Karlsson J, Lin L, Gunnes S, Sylven C, Astrom H: Muscle ubiquinone in male effort angina patients. Mol Cell Biochem. 1996 Mar 23;156(2):173-8. doi: 10.1007/BF00426341. [PubMed:9095475 ]
Yamashita S, Yamamoto Y: Simultaneous detection of ubiquinol and ubiquinone in human plasma as a marker of oxidative stress. Anal Biochem. 1997 Jul 15;250(1):66-73. doi: 10.1006/abio.1997.2187. [PubMed:9234900 ]
Mancini A, Conte G, Milardi D, De Marinis L, Littarru GP: Relationship between sperm cell ubiquinone and seminal parameters in subjects with and without varicocele. Andrologia. 1998 Feb-Mar;30(1):1-4. doi: 10.1111/j.1439-0272.1998.tb01374.x. [PubMed:9567163 ]
Zhang Y, Eriksson M, Dallner G, Appelkvist EL: Analysis of ubiquinone and tocopherol levels in normal and hyperlipidemic human plasma. Lipids. 1998 Aug;33(8):811-5. doi: 10.1007/s11745-998-0274-y. [PubMed:9727612 ]
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Showing metabocard for Ubiquinone Q1 (MMDBc0032915)

MOL for #<Metabolite:0x00007fd1014e32c8>

3D MOL for #<Metabolite:0x00007fd1014e32c8>

3D SDF for #<Metabolite:0x00007fd1014e32c8>

3D-SDF for #<Metabolite:0x00007fd1014e32c8>

PDB for #<Metabolite:0x00007fd1014e32c8>

3D PDB for #<Metabolite:0x00007fd1014e32c8>

SMILES for #<Metabolite:0x00007fd1014e32c8>

INCHI for #<Metabolite:0x00007fd1014e32c8>

Structure for #<Metabolite:0x00007fd1014e32c8>

3D Structure for #<Metabolite:0x00007fd1014e32c8>