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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:55:47 UTC

Update Date

2022-03-07 03:17:43 UTC

HMDB ID

HMDB0060352

Secondary Accession Numbers

HMDB60352

Metabolite Identification

Common Name

2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone

Description

2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 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). 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060352
     RDKit          3D
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.8531    0.3118    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093   -0.6400    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0214   -0.1688   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086    0.6001   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3267    0.9595   -1.6214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    1.0656   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685    1.8011   -2.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375    0.7063   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.1881   -1.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479   -0.0502   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -0.5175    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610   -0.1817    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072   -1.0213   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -2.4587   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -0.5126   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521   -1.0306    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7072   -0.4128   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5111    0.3504    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7378    0.8975   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3113    0.7360    1.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7272   -0.5162    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -1.2636    1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904    0.5533    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7585   -0.0857    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171    1.2731    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    1.9292   -1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    1.5698   -2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    2.1136   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010    0.4053   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758   -1.6494    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.2229    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479    0.8820    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.8710    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.6257   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -3.0706   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.5978   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.7804   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -0.7826    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866   -2.1250    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9421   -0.6357   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5955    0.3284    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709    0.7821   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504    1.9383    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804    0.7104    2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110    0.1069    2.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283    1.8166    2.0122 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  2  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv0541 10181208542D          

 22 22  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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 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
    2.1434   -0.4125    0.0000 O   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
    0.7145   -1.2375    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
   -0.7145   -0.4125    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   -1.6500    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 10 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060352

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O4/c1-11(2)7-6-8-12(3)9-10-14-13(4)15(19)17(21)18(22-5)16(14)20/h7,9,21H,6,8,10H2,1-5H3/b12-9+

> <INCHI_KEY>
JVLAJUCFVRPDAQ-FMIVXFBMSA-N

> <FORMULA>
C18H24O4

> <MOLECULAR_WEIGHT>
304.3808

> <EXACT_MASS>
304.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.070974598442774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
3.765586701666667

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.311634572670004

> <JCHEM_PKA_STRONGEST_BASIC>
-4.092751037914863

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
91.43319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060352
     RDKit          3D
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.8531    0.3118    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093   -0.6400    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0214   -0.1688   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086    0.6001   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3267    0.9595   -1.6214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    1.0656   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685    1.8011   -2.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375    0.7063   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.1881   -1.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479   -0.0502   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -0.5175    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610   -0.1817    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072   -1.0213   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -2.4587   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -0.5126   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521   -1.0306    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7072   -0.4128   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5111    0.3504    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7378    0.8975   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3113    0.7360    1.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7272   -0.5162    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -1.2636    1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904    0.5533    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7585   -0.0857    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171    1.2731    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    1.9292   -1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    1.5698   -2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    2.1136   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010    0.4053   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758   -1.6494    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.2229    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479    0.8820    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.8710    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.6257   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -3.0706   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.5978   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.7804   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -0.7826    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866   -2.1250    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9421   -0.6357   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5955    0.3284    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709    0.7821   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504    1.9383    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804    0.7104    2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110    0.1069    2.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283    1.8166    2.0122 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  2  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 18-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-12         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   10    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0060352
HETATM    1  C1  UNL     1       6.853   0.312   1.452  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.209  -0.640   0.604  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.021  -0.169  -0.009  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.109   0.600  -1.080  1.00  0.00           C  
HETATM    5  O2  UNL     1       6.327   0.959  -1.621  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.871   1.066  -1.684  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.869   1.801  -2.705  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.537   0.706  -1.139  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.306   1.188  -1.770  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.448  -0.050  -0.085  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.276  -0.517   0.605  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.061  -0.182   0.216  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.007  -1.021  -0.150  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.725  -2.459  -0.184  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.325  -0.513  -0.519  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.452  -1.031   0.332  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.707  -0.413  -0.182  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.511   0.350   0.506  1.00  0.00           C  
HETATM   19  C16 UNL     1      -6.738   0.897  -0.153  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.311   0.736   1.926  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.727  -0.516   0.518  1.00  0.00           C  
HETATM   22  O4  UNL     1       3.723  -1.264   1.556  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.090   0.553   2.244  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.759  -0.086   1.913  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.017   1.273   0.905  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.607   1.929  -1.516  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.627   1.570  -2.802  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.889   2.114  -1.330  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.601   0.405  -2.035  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.376  -1.649   0.680  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.420  -0.223   1.696  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.348   0.882   0.228  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.384  -2.871   0.786  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.126  -2.626  -0.907  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.556  -3.071  -0.573  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.366   0.598  -0.487  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.495  -0.780  -1.603  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.237  -0.783   1.373  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.587  -2.125   0.244  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.942  -0.636  -1.215  1.00  0.00           H  
HETATM   41  H19 UNL     1      -7.596   0.328   0.262  1.00  0.00           H  
HETATM   42  H20 UNL     1      -6.671   0.782  -1.272  1.00  0.00           H  
HETATM   43  H21 UNL     1      -6.850   1.938   0.160  1.00  0.00           H  
HETATM   44  H22 UNL     1      -4.280   0.710   2.270  1.00  0.00           H  
HETATM   45  H23 UNL     1      -6.011   0.107   2.534  1.00  0.00           H  
HETATM   46  H24 UNL     1      -5.628   1.817   2.012  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5    6
CONECT    5   26
CONECT    6    7    7    8
CONECT    8    9   10   10
CONECT    9   27   28   29
CONECT   10   11   21
CONECT   11   12   30   31
CONECT   12   13   13   32
CONECT   13   14   15
CONECT   14   33   34   35
CONECT   15   16   36   37
CONECT   16   17   38   39
CONECT   17   18   18   40
CONECT   18   19   20
CONECT   19   41   42   43
CONECT   20   44   45   46
CONECT   21   22   22
END

HMDB0060352
     RDKit          3D
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
 46 46  0  0  0  0  0  0  0  0999 V2000
    6.8531    0.3118    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093   -0.6400    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0214   -0.1688   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086    0.6001   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3267    0.9595   -1.6214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    1.0656   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685    1.8011   -2.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375    0.7063   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.1881   -1.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479   -0.0502   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -0.5175    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610   -0.1817    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072   -1.0213   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -2.4587   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -0.5126   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521   -1.0306    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7072   -0.4128   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5111    0.3504    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7378    0.8975   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3113    0.7360    1.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7272   -0.5162    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -1.2636    1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904    0.5533    2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7585   -0.0857    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171    1.2731    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    1.9292   -1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    1.5698   -2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    2.1136   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010    0.4053   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758   -1.6494    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.2229    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479    0.8820    0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.8710    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.6257   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561   -3.0706   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.5978   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.7804   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -0.7826    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866   -2.1250    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9421   -0.6357   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5955    0.3284    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6709    0.7821   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8504    1.9383    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804    0.7104    2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110    0.1069    2.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283    1.8166    2.0122 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  2  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄O₄

Average Molecular Weight

304.3808

Monoisotopic Molecular Weight

304.167459256

IUPAC Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O

InChI Identifier

InChI=1S/C18H24O4/c1-11(2)7-6-8-12(3)9-10-14-13(4)15(19)17(21)18(22-5)16(14)20/h7,9,21H,6,8,10H2,1-5H3/b12-9+

InChI Key

JVLAJUCFVRPDAQ-FMIVXFBMSA-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
Vinylogous acid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060352)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.09	ALOGPS
logP	3.77	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.43 m³·mol⁻¹	ChemAxon
Polarizability	34.07 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	179.712	30932474
DeepCCS	[M-H]-	177.354	30932474
DeepCCS	[M-2H]-	210.301	30932474
DeepCCS	[M+Na]+	185.806	30932474
AllCCS	[M+H]+	175.1	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	178.1	32859911
AllCCS	[M+Na]+	179.0	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	180.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone	COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O	3197.4	Standard polar	33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone	COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O	2041.8	Standard non polar	33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone	COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O	2208.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(=O)C(C)=C(C/C=C(\C)CCC=C(C)C)C1=O	2320.5	Semi standard non polar	33892256
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)=C(C/C=C(\C)CCC=C(C)C)C1=O	2558.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3490000000-0edba616b6e1e0c917ed	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (1 TMS) - 70eV, Positive	splash10-03k9-6649000000-b8f9f1d637fe5d24c5f3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 10V, Positive-QTOF	splash10-0a4i-0569000000-dd7efcdfd9d0f9480c48	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 20V, Positive-QTOF	splash10-0ac0-4931000000-3e688836d12c6b05367a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 40V, Positive-QTOF	splash10-0690-9410000000-edf9000e56282cac9436	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 10V, Negative-QTOF	splash10-0udi-0049000000-5bb1699e50e42794d100	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 20V, Negative-QTOF	splash10-0udj-1192000000-ecde9d15182449181856	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone 40V, Negative-QTOF	splash10-0uk9-7790000000-465875fa98b66e16ae83	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

C17562

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135437103

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. 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.

Enzymes

Enzyme Details

1. Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial

General function:: Involved in methyltransferase activity
Specific function:: Not Available
Gene Name:: COQ3
Uniprot ID:: Q9NZJ6
Molecular weight:: 41053.76

Reactions

2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → Ubiquinone-2 + S-Adenosylhomocysteine	details

Enzyme Details

2. Ubiquinone biosynthesis protein COQ7 homolog

General function:: Involved in oxidoreductase activity
Specific function:: Involved in lifespan determination in ubiquinone-independent manner. Involved in ubiquinone biosynthesis. Potential central metabolic regulator (By similarity).
Gene Name:: COQ7
Uniprot ID:: Q99807
Molecular weight:: Not Available

Reactions

2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + Oxygen + NADPH + Hydrogen Ion → 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + Water	details

Showing metabocard for 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone (HMDB0060352)

MOL for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

3D MOL for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

3D SDF for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

3D-SDF for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

PDB for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

3D PDB for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

SMILES for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

INCHI for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

Structure for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

3D Structure for HMDB0060352 (2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions