MiMeDB: Showing metabocard for Ubiquinol-1 (MMDBc0031711)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:45:21 UTC

Update Date

2024-04-30 19:51:36 UTC

Metabolite ID

MMDBc0031711

Metabolite Identification

Common Name

Ubiquinol-1

Description

Ubiquinol-1 is a member of the chemical class known as Polyprenylbenzoquinols. They are reduced forms of polyprenylbenzoquinines (ubiquinones). These are compounds containing a polyisoprene chain attached to a quinol at the second ring position. Ubiquiol-1 has just 1 isoprene unit. Normally in E. coli the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-1 is a ‚Äúfailed‚Äù or incomplete version of Ubiquinol 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Coenzyme Q(n) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinones or ubisemiquinones), and fully reduced (ubiquinols). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form. Ubiquionols are important in cellular respiration. They are fat-soluble and therefore mobile in cellular membranes; they play a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.

Structure

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

HMDB0059661
     RDKit          3D
QH(2)
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3620    2.0679   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118    1.1093   -1.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145    0.7037   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641    1.3818   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.4757   -1.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512    1.0188   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2775    1.8032   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -0.0384    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205   -0.4389    1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3009   -1.1864    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -0.8417   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379    0.3745    0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2412   -1.7327   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -0.7263    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.7959    1.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -0.3581    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042   -1.0749    0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -2.2020   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595    3.0772   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4180    1.7763   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681    2.1261    0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0518    2.7433   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748    2.1298    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137    1.2471   -1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7302   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616    0.4524    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368   -1.1520    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763   -2.1042   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315    0.9810    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.9881   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    0.0975    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1325   -2.0948   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907   -1.0703   -1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084   -2.5376   -1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078   -2.3111    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -3.1178    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016   -2.1736   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -2.3274   -0.9845 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 10101207532D          

 18 18  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031711

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3

> <INCHI_KEY>
TVLSKGDBUQMDPR-UHFFFAOYSA-N

> <FORMULA>
C14H20O4

> <MOLECULAR_WEIGHT>
252.3062

> <EXACT_MASS>
252.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.926930356843464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.29276103

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.153761772717798

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.266549466913968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.66491908590501

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
72.23020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059661
     RDKit          3D
QH(2)
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3620    2.0679   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118    1.1093   -1.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145    0.7037   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641    1.3818   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.4757   -1.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512    1.0188   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2775    1.8032   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -0.0384    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205   -0.4389    1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3009   -1.1864    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -0.8417   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379    0.3745    0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2412   -1.7327   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -0.7263    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.7959    1.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -0.3581    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042   -1.0749    0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -2.2020   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595    3.0772   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4180    1.7763   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681    2.1261    0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0518    2.7433   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748    2.1298    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137    1.2471   -1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7302   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616    0.4524    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368   -1.1520    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763   -2.1042   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315    0.9810    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.9881   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    0.0975    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1325   -2.0948   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907   -1.0703   -1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084   -2.5376   -1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078   -2.3111    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -3.1178    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016   -2.1736   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -2.3274   -0.9845 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15    9   16                                                       
CONECT   16   15                                                            
CONECT   17    8                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0059661
HETATM    1  C1  UNL     1      -4.362   2.068  -0.528  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.512   1.109  -1.121  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.315   0.704  -0.530  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.164   1.382  -0.828  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.156   2.476  -1.713  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.051   1.019  -0.269  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.278   1.803  -0.635  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.127  -0.038   0.605  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.421  -0.439   1.211  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.301  -1.186   0.276  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.500  -0.842  -0.101  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.238   0.375   0.329  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.241  -1.733  -1.059  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.030  -0.726   0.909  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.973  -1.796   1.788  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.250  -0.358   0.344  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.404  -1.075   0.673  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.832  -2.202  -0.061  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.160   3.077  -0.968  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.418   1.776  -0.752  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.268   2.126   0.565  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.052   2.743  -2.125  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.775   2.130   0.306  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.914   1.247  -1.324  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.969   2.730  -1.157  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.862   0.452   1.649  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.237  -1.152   2.070  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.876  -2.104  -0.116  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.732   0.981   1.073  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.409   0.988  -0.590  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.257   0.098   0.733  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.132  -2.095  -0.505  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.591  -1.070  -1.883  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.608  -2.538  -1.446  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.808  -2.311   2.023  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.682  -3.118   0.566  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.902  -2.174  -0.307  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.229  -2.327  -0.985  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5    6
CONECT    5   22
CONECT    6    7    8    8
CONECT    7   23   24   25
CONECT    8    9   14
CONECT    9   10   26   27
CONECT   10   11   11   28
CONECT   11   12   13
CONECT   12   29   30   31
CONECT   13   32   33   34
CONECT   14   15   16   16
CONECT   15   35
CONECT   16   17
CONECT   17   18
CONECT   18   36   37   38
END

HMDB0059661
     RDKit          3D
QH(2)
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3620    2.0679   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118    1.1093   -1.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145    0.7037   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641    1.3818   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.4757   -1.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512    1.0188   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2775    1.8032   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -0.0384    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205   -0.4389    1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3009   -1.1864    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -0.8417   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379    0.3745    0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2412   -1.7327   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -0.7263    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.7959    1.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -0.3581    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042   -1.0749    0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -2.2020   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1595    3.0772   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4180    1.7763   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681    2.1261    0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0518    2.7433   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748    2.1298    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137    1.2471   -1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7302   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616    0.4524    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368   -1.1520    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763   -2.1042   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315    0.9810    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.9881   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    0.0975    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1325   -2.0948   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907   -1.0703   -1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084   -2.5376   -1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078   -2.3111    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -3.1178    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016   -2.1736   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -2.3274   -0.9845 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
M  END

Synonyms

Value	Source
Ubiquinol	HMDB
Ubiquinol 0	HMDB
Ubiquinol 1	HMDB
Ubiquinol 50	HMDB
Ubiquinol 7	HMDB
Ubiquinol 6 (ubiquinol 30)	HMDB
Ubiquinol 9	HMDB
Ubiquinols	HMDB
Ubiquinone hydroquinone	HMDB

Molecular Formula

C₁₄H₂₀O₄

Average Mass

252.3062

Monoisotopic Mass

252.136159128

IUPAC Name

2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

Traditional Name

2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC

InChI Identifier

InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3

InChI Key

TVLSKGDBUQMDPR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol 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

Ubiquinols

Alternative Parents

Substituents

Ubiquinol skeleton
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Hydroquinone
M-cresol
Phenoxy compound
O-cresol
Phenol ether
Methoxybenzene
Alkyl aryl ether
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a ubiquinol (CPD0-2061 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.7	ALOGPS
logP	3.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.23 m³·mol⁻¹	ChemAxon
Polarizability	27.93 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	splash10-000l-4290000000-f4931613b9126eb83a43	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-2019000000-8e5ad437d5286cc0bc2a	2017-10-06	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-a6ad04484f30fd3e6542	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-3890000000-88f5855287f7c4803858	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-6910000000-2566d9b9220bdfd47f6e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-d3c87a4ee5f1fc3e1e44	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-1790000000-f43f7dda07b2e0c3a516	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00y0-8920000000-223ce579fce165e10c55	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-23afefc78640d53f4f60	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0190000000-cbc2308da177796deed8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2920000000-059a3fa2f55e31d2b4b2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-b042dd8069485cebe38b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-0960000000-1542fd39196840ebf34d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-4910000000-53135d0f8e2b249423c5	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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
MMDBp0191791	NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial	Unknown	O75306	Homo sapiens
MMDBp0191803	NADH-ubiquinone oxidoreductase chain 4L	Unknown	P03901	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
MMDBp0191813	NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial	Unknown	P19404	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
MMDBp0191833	NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial	Unknown	P28331	Homo sapiens
MMDBp0191847	Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial	Unknown	Q16134	Homo sapiens
MMDBp0191849	NADH-ubiquinone oxidoreductase chain 4	Unknown	P03905	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
MMDBp0191860	NADH-ubiquinone oxidoreductase chain 6	Unknown	P03923	Homo sapiens
MMDBp0191864	Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Unknown	P21912	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
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	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0059661

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

447920

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Ubiquinol-1 (MMDBc0031711)

MOL for #<Metabolite:0x00007fece43f9980>

3D MOL for #<Metabolite:0x00007fece43f9980>

3D SDF for #<Metabolite:0x00007fece43f9980>

3D-SDF for #<Metabolite:0x00007fece43f9980>

PDB for #<Metabolite:0x00007fece43f9980>

3D PDB for #<Metabolite:0x00007fece43f9980>

SMILES for #<Metabolite:0x00007fece43f9980>

INCHI for #<Metabolite:0x00007fece43f9980>

Structure for #<Metabolite:0x00007fece43f9980>

3D Structure for #<Metabolite:0x00007fece43f9980>