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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:19:59 UTC

Update Date

2022-03-07 02:51:21 UTC

HMDB ID

HMDB0012146

Secondary Accession Numbers

HMDB12146

Metabolite Identification

Common Name

2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol

Description

2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is an ubiquinone derivative that is an intermediate in ubiquinone-6 biosynthesis. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes ubiquinone is found mostly within the inner mitochondrial membrane, where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate , while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway , which feeds isoprene units into the Polyprenyl Biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain vary in different species. For example, Saccharomyces cerevisiae subsp (S288c) has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. The ubiquinones are often named according to the number of carbons in the side chain or the number of isoprenoid subunits. The ubiquinone biosynthesis pathway has been elucidated primarily by the use of mutant strains that accumulate pathway intermediates. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is a substrate for hexaprenyldihydroxybenzoate methyltransferase, mitochondrial precursor (COQ3) and can be generated from 2-hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol. Then it can be converted to ubiquinol-6.(BioCyc).

Structure

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


  Mrv0541 02241203472D          

 42 42  0  0  0  0            999 V2000
   10.3462  -14.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5213  -14.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088  -15.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5213  -15.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088  -16.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5213  -17.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3462  -17.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7587  -16.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -16.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960  -15.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -15.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960  -14.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -13.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960  -12.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -12.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960  -11.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -10.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960  -10.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836   -9.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960   -8.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836   -7.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9960   -7.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836   -6.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7587   -6.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3462   -5.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7587   -5.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3462   -4.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7587   -3.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3462   -2.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5213   -4.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088   -5.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2840   -5.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5213   -5.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088   -6.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088   -3.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836   -5.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8209   -7.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8209  -10.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8209  -12.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8209  -15.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088  -17.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1088  -13.6124    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
  2 42  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 41  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 40  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 39  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 38  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 37  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 33  1  0  0  0  0
 26 27  1  0  0  0  0
 26 36  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  2  0  0  0  0
 28 29  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
M  END

HMDB0012146
     RDKit          3D
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
100100  0  0  0  0  0  0  0  0999 V2000
  -12.8216   -1.9851    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2439   -0.9416   -0.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9023   -0.8293   -0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3564   -1.3567   -2.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2036   -2.0232   -2.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0143   -1.2289   -2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4361   -1.7557   -3.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1862   -0.5469   -1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7353   -0.4381   -1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7413   -0.0277   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8760    0.7088    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5976    2.0769    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4251    2.6011   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2650   -1.3961    1.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097   -1.4718    1.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.8104    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4119   -0.2391    1.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112   -0.3350    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2405    0.7766   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390    2.0900   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0437   -0.4350   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7611    0.0681   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0504   -0.1254   -2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 93  1  0
 39 94  1  0
 39 95  1  0
 39 96  1  0
 40 97  1  0
 40 98  1  0
 40 99  1  0
 42100  1  0
M  END


  Mrv0541 02241203472D          

 42 42  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 42  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 41  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 18 38  1  0  0  0  0
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 22 23  2  0  0  0  0
 22 37  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 33  1  0  0  0  0
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 27 30  2  0  0  0  0
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 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012146

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(O)=C(C)C(C\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CCC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3/b28-17-,29-19+,30-21+,31-23+,32-25-

> <INCHI_KEY>
ZQXNZNKHQXLVCV-QXVHJBQVSA-N

> <FORMULA>
C38H58O4

> <MOLECULAR_WEIGHT>
578.8647

> <EXACT_MASS>
578.433510344

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
72.48513220004254

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol

> <ALOGPS_LOGP>
8.32

> <JCHEM_LOGP>
11.445438349000002

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.512154695235251

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.959557571533354

> <JCHEM_PKA_STRONGEST_BASIC>
-4.781071451386308

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
186.7609000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.45e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012146
     RDKit          3D
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
100100  0  0  0  0  0  0  0  0999 V2000
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 33 34  1  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  3
 38 39  1  0
 38 40  1  0
 10 41  2  0
 41 42  1  0
 41  3  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  5 46  1  0
  7 47  1  0
  9 48  1  0
  9 49  1  0
  9 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 14 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  0
 19 62  1  0
 19 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 21 67  1  0
 21 68  1  0
 22 69  1  0
 24 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  0
 25 74  1  0
 26 75  1  0
 26 76  1  0
 27 77  1  0
 29 78  1  0
 29 79  1  0
 29 80  1  0
 30 81  1  0
 30 82  1  0
 31 83  1  0
 31 84  1  0
 32 85  1  0
 34 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 35 90  1  0
 36 91  1  0
 36 92  1  0
 37 93  1  0
 39 94  1  0
 39 95  1  0
 39 96  1  0
 40 97  1  0
 40 98  1  0
 40 99  1  0
 42100  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.313 -26.744   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.773 -26.744   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.003 -28.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.773 -29.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.003 -30.744   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.773 -32.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.313 -32.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.083 -30.744   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.623 -30.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.393 -29.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.623 -28.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.393 -26.744   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.623 -25.410   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.393 -24.076   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.623 -22.742   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.393 -21.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.623 -20.076   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.393 -18.742   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.623 -17.409   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.393 -16.075   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.623 -14.741   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.393 -13.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.623 -12.075   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.083 -12.075   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.313 -10.741   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.083  -9.407   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.313  -8.073   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.083  -6.740   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.313  -5.407   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.773  -8.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.003  -9.407   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.463  -9.407   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      17.773 -10.741   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.003 -12.075   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.003  -6.740   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      21.623  -9.407   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      23.932 -13.407   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.932 -18.742   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.932 -24.076   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      23.932 -29.410   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.003 -33.411   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.003 -25.410   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   41                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   40                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   38                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   36                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   25   31   34                                                  
CONECT   34   33                                                            
CONECT   35   30                                                            
CONECT   36   26                                                            
CONECT   37   22                                                            
CONECT   38   18                                                            
CONECT   39   14                                                            
CONECT   40   10                                                            
CONECT   41    6                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

COMPND    HMDB0012146
HETATM    1  C1  UNL     1     -12.822  -1.985   0.099  1.00  0.00           C  
HETATM    2  O1  UNL     1     -12.244  -0.942  -0.635  1.00  0.00           O  
HETATM    3  C2  UNL     1     -10.902  -0.829  -0.943  1.00  0.00           C  
HETATM    4  C3  UNL     1     -10.356  -1.357  -2.085  1.00  0.00           C  
HETATM    5  O2  UNL     1     -11.204  -2.023  -2.947  1.00  0.00           O  
HETATM    6  C4  UNL     1      -9.014  -1.229  -2.366  1.00  0.00           C  
HETATM    7  O3  UNL     1      -8.436  -1.756  -3.518  1.00  0.00           O  
HETATM    8  C5  UNL     1      -8.186  -0.547  -1.470  1.00  0.00           C  
HETATM    9  C6  UNL     1      -6.735  -0.438  -1.811  1.00  0.00           C  
HETATM   10  C7  UNL     1      -8.741  -0.028  -0.339  1.00  0.00           C  
HETATM   11  C8  UNL     1      -7.876   0.709   0.620  1.00  0.00           C  
HETATM   12  C9  UNL     1      -7.598   2.077   0.171  1.00  0.00           C  
HETATM   13  C10 UNL     1      -6.425   2.601  -0.008  1.00  0.00           C  
HETATM   14  C11 UNL     1      -6.335   4.044  -0.479  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.171   1.871   0.222  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.323   2.533   1.297  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.078   1.695   1.437  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.888   2.237   1.257  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.848   3.687   0.915  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.671   1.411   1.397  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.051   0.003   1.720  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.145  -0.876   1.909  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.329  -1.880   1.070  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.692  -2.070  -0.026  1.00  0.00           C  
HETATM   25  C22 UNL     1       1.444  -2.835   1.076  1.00  0.00           C  
HETATM   26  C23 UNL     1       2.508  -2.647   2.082  1.00  0.00           C  
HETATM   27  C24 UNL     1       3.265  -1.396   1.897  1.00  0.00           C  
HETATM   28  C25 UNL     1       4.610  -1.472   1.731  1.00  0.00           C  
HETATM   29  C26 UNL     1       5.252  -2.810   1.741  1.00  0.00           C  
HETATM   30  C27 UNL     1       5.412  -0.239   1.552  1.00  0.00           C  
HETATM   31  C28 UNL     1       6.111  -0.335   0.197  1.00  0.00           C  
HETATM   32  C29 UNL     1       6.934   0.849  -0.071  1.00  0.00           C  
HETATM   33  C30 UNL     1       8.241   0.777  -0.249  1.00  0.00           C  
HETATM   34  C31 UNL     1       8.939   2.090  -0.516  1.00  0.00           C  
HETATM   35  C32 UNL     1       9.044  -0.435  -0.171  1.00  0.00           C  
HETATM   36  C33 UNL     1       9.775  -0.862  -1.390  1.00  0.00           C  
HETATM   37  C34 UNL     1      10.761   0.068  -1.945  1.00  0.00           C  
HETATM   38  C35 UNL     1      12.050  -0.125  -2.009  1.00  0.00           C  
HETATM   39  C36 UNL     1      12.936   0.903  -2.599  1.00  0.00           C  
HETATM   40  C37 UNL     1      12.647  -1.375  -1.489  1.00  0.00           C  
HETATM   41  C38 UNL     1     -10.079  -0.151  -0.052  1.00  0.00           C  
HETATM   42  O4  UNL     1     -10.681   0.358   1.076  1.00  0.00           O  
HETATM   43  H1  UNL     1     -12.570  -1.857   1.181  1.00  0.00           H  
HETATM   44  H2  UNL     1     -13.924  -1.937  -0.055  1.00  0.00           H  
HETATM   45  H3  UNL     1     -12.442  -2.974  -0.211  1.00  0.00           H  
HETATM   46  H4  UNL     1     -10.963  -2.453  -3.801  1.00  0.00           H  
HETATM   47  H5  UNL     1      -9.003  -2.244  -4.167  1.00  0.00           H  
HETATM   48  H6  UNL     1      -6.517  -1.032  -2.746  1.00  0.00           H  
HETATM   49  H7  UNL     1      -6.446   0.591  -2.063  1.00  0.00           H  
HETATM   50  H8  UNL     1      -6.112  -0.889  -1.011  1.00  0.00           H  
HETATM   51  H9  UNL     1      -6.979   0.083   0.770  1.00  0.00           H  
HETATM   52  H10 UNL     1      -8.353   0.806   1.632  1.00  0.00           H  
HETATM   53  H11 UNL     1      -8.458   2.765  -0.045  1.00  0.00           H  
HETATM   54  H12 UNL     1      -7.279   4.301  -1.012  1.00  0.00           H  
HETATM   55  H13 UNL     1      -6.239   4.741   0.356  1.00  0.00           H  
HETATM   56  H14 UNL     1      -5.523   4.093  -1.231  1.00  0.00           H  
HETATM   57  H15 UNL     1      -4.617   1.913  -0.772  1.00  0.00           H  
HETATM   58  H16 UNL     1      -5.270   0.809   0.432  1.00  0.00           H  
HETATM   59  H17 UNL     1      -4.864   2.435   2.258  1.00  0.00           H  
HETATM   60  H18 UNL     1      -4.097   3.567   1.038  1.00  0.00           H  
HETATM   61  H19 UNL     1      -3.248   0.657   1.690  1.00  0.00           H  
HETATM   62  H20 UNL     1      -2.311   4.311   1.705  1.00  0.00           H  
HETATM   63  H21 UNL     1      -2.355   3.923  -0.035  1.00  0.00           H  
HETATM   64  H22 UNL     1      -0.778   4.023   0.873  1.00  0.00           H  
HETATM   65  H23 UNL     1       0.042   1.847   2.140  1.00  0.00           H  
HETATM   66  H24 UNL     1      -0.142   1.477   0.405  1.00  0.00           H  
HETATM   67  H25 UNL     1      -1.699  -0.361   0.907  1.00  0.00           H  
HETATM   68  H26 UNL     1      -1.627  -0.084   2.664  1.00  0.00           H  
HETATM   69  H27 UNL     1       0.837  -0.713   2.727  1.00  0.00           H  
HETATM   70  H28 UNL     1      -1.687  -2.306   0.357  1.00  0.00           H  
HETATM   71  H29 UNL     1      -0.396  -2.877  -0.714  1.00  0.00           H  
HETATM   72  H30 UNL     1      -0.693  -1.142  -0.659  1.00  0.00           H  
HETATM   73  H31 UNL     1       1.894  -2.791   0.041  1.00  0.00           H  
HETATM   74  H32 UNL     1       0.985  -3.859   1.221  1.00  0.00           H  
HETATM   75  H33 UNL     1       3.204  -3.537   2.002  1.00  0.00           H  
HETATM   76  H34 UNL     1       2.140  -2.702   3.137  1.00  0.00           H  
HETATM   77  H35 UNL     1       2.876  -0.394   1.868  1.00  0.00           H  
HETATM   78  H36 UNL     1       4.957  -3.437   0.867  1.00  0.00           H  
HETATM   79  H37 UNL     1       6.345  -2.660   1.636  1.00  0.00           H  
HETATM   80  H38 UNL     1       5.103  -3.339   2.708  1.00  0.00           H  
HETATM   81  H39 UNL     1       6.129  -0.071   2.382  1.00  0.00           H  
HETATM   82  H40 UNL     1       4.778   0.669   1.505  1.00  0.00           H  
HETATM   83  H41 UNL     1       6.606  -1.283   0.020  1.00  0.00           H  
HETATM   84  H42 UNL     1       5.241  -0.327  -0.539  1.00  0.00           H  
HETATM   85  H43 UNL     1       6.461   1.843  -0.128  1.00  0.00           H  
HETATM   86  H44 UNL     1       8.706   2.453  -1.531  1.00  0.00           H  
HETATM   87  H45 UNL     1       8.506   2.880   0.162  1.00  0.00           H  
HETATM   88  H46 UNL     1       9.985   1.976  -0.257  1.00  0.00           H  
HETATM   89  H47 UNL     1       8.541  -1.331   0.247  1.00  0.00           H  
HETATM   90  H48 UNL     1       9.866  -0.241   0.610  1.00  0.00           H  
HETATM   91  H49 UNL     1      10.328  -1.826  -1.182  1.00  0.00           H  
HETATM   92  H50 UNL     1       9.010  -1.172  -2.162  1.00  0.00           H  
HETATM   93  H51 UNL     1      10.369   1.004  -2.356  1.00  0.00           H  
HETATM   94  H52 UNL     1      12.397   1.882  -2.575  1.00  0.00           H  
HETATM   95  H53 UNL     1      13.893   1.035  -2.036  1.00  0.00           H  
HETATM   96  H54 UNL     1      13.162   0.706  -3.669  1.00  0.00           H  
HETATM   97  H55 UNL     1      13.737  -1.195  -1.287  1.00  0.00           H  
HETATM   98  H56 UNL     1      12.227  -1.635  -0.489  1.00  0.00           H  
HETATM   99  H57 UNL     1      12.496  -2.256  -2.148  1.00  0.00           H  
HETATM  100  H58 UNL     1     -10.276   0.864   1.811  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3
CONECT    3    4    4   41
CONECT    4    5    6
CONECT    5   46
CONECT    6    7    8    8
CONECT    7   47
CONECT    8    9   10
CONECT    9   48   49   50
CONECT   10   11   41   41
CONECT   11   12   51   52
CONECT   12   13   13   53
CONECT   13   14   15
CONECT   14   54   55   56
CONECT   15   16   57   58
CONECT   16   17   59   60
CONECT   17   18   18   61
CONECT   18   19   20
CONECT   19   62   63   64
CONECT   20   21   65   66
CONECT   21   22   67   68
CONECT   22   23   23   69
CONECT   23   24   25
CONECT   24   70   71   72
CONECT   25   26   73   74
CONECT   26   27   75   76
CONECT   27   28   28   77
CONECT   28   29   30
CONECT   29   78   79   80
CONECT   30   31   81   82
CONECT   31   32   83   84
CONECT   32   33   33   85
CONECT   33   34   35
CONECT   34   86   87   88
CONECT   35   36   89   90
CONECT   36   37   91   92
CONECT   37   38   38   93
CONECT   38   39   40
CONECT   39   94   95   96
CONECT   40   97   98   99
CONECT   41   42
CONECT   42  100
END

HMDB0012146
     RDKit          3D
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
100100  0  0  0  0  0  0  0  0999 V2000
  -12.8216   -1.9851    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2439   -0.9416   -0.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9023   -0.8293   -0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3564   -1.3567   -2.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2036   -2.0232   -2.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0143   -1.2289   -2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4361   -1.7557   -3.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1862   -0.5469   -1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7353   -0.4381   -1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7413   -0.0277   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8760    0.7088    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5976    2.0769    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4251    2.6011   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3350    4.0437   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    1.8713    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3229    2.5331    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0777    1.6950    1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884    2.2370    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476    3.6872    0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.4112    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0508    0.0026    1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454   -0.8757    1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3289   -1.8797    1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.0699   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -2.8352    1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6471    2.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650   -1.3961    1.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097   -1.4718    1.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.8104    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4119   -0.2391    1.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112   -0.3350    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9343    0.8491   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2405    0.7766   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390    2.0900   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0437   -0.4350   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7750   -0.8616   -1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7611    0.0681   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0504   -0.1254   -2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9357    0.9032   -2.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6469   -1.3754   -1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0795   -0.1513   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6806    0.3585    1.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5704   -1.8572    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9236   -1.9370   -0.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4417   -2.9743   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9626   -2.4527   -3.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0029   -2.2438   -4.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5173   -1.0316   -2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4457    0.5909   -2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1121   -0.8891   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9794    0.0830    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3529    0.8060    1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4580    2.7648   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2795    4.3014   -1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2395    4.7413    0.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5231    4.0927   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    1.9128   -0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2696    0.8088    0.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8637    2.4353    2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    3.5666    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2476    0.6568    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    4.3112    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554    3.9231   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    4.0235    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0418    1.8471    2.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1419    1.4771    0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989   -0.3613    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265   -0.0838    2.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369   -0.7133    2.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872   -2.3063    0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -2.8767   -0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931   -1.1423   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -2.7913    0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9849   -3.8586    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -3.5368    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396   -2.7022    3.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -0.3940    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9568   -3.4374    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3453   -2.6600    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1031   -3.3386    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1295   -0.0714    2.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780    0.6693    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6057   -1.2832    0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415   -0.3273   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4606    1.8425   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7059    2.4530   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5060    2.8799    0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9855    1.9756   -0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5413   -1.3306    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8658   -0.2406    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3275   -1.8262   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0099   -1.1717   -2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687    1.0037   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3972    1.8817   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8935    1.0351   -2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1625    0.7062   -3.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7368   -1.1953   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2268   -1.6346   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4959   -2.2555   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2762    0.8644    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Demethyl-ubiquinol-6	HMDB

Chemical Formula

C₃₈H₅₈O₄

Average Molecular Weight

578.8647

Monoisotopic Molecular Weight

578.433510344

IUPAC Name

5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol

Traditional Name

5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(O)=C(C)C(C\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CCC=C(C)C)=C1O

InChI Identifier

InChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3/b28-17-,29-19+,30-21+,31-23+,32-25-

InChI Key

ZQXNZNKHQXLVCV-QXVHJBQVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-Polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenylphenols

Direct Parent

2-polyprenyl-6-methoxyphenols

Alternative Parents

Substituents

2-polyprenyl-6-methoxyphenol
Polyprenylbenzoquinol
Sesterterpenoid
Prenylbenzoquinol
Ubiquinol skeleton
Methoxyphenol
Hydroxyquinol derivative
Anisole
Phenoxy compound
M-cresol
O-cresol
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
Toluene
Monocyclic benzene moiety
Benzenoid
Ether
Polyol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012146)
Membrane (HMDB: HMDB0012146)

Source

Exogenous

Exogenous (HMDB: HMDB0012146)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0012146)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	0.00064 g/L	ALOGPS
logP	8.32	ALOGPS
logP	11.45	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	186.76 m³·mol⁻¹	ChemAxon
Polarizability	72.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	243.741	30932474
DeepCCS	[M-H]-	241.345	30932474
DeepCCS	[M-2H]-	274.427	30932474
DeepCCS	[M+Na]+	249.653	30932474
AllCCS	[M+H]+	247.6	32859911
AllCCS	[M+H-H2O]+	246.2	32859911
AllCCS	[M+NH4]+	248.9	32859911
AllCCS	[M+Na]+	249.3	32859911
AllCCS	[M-H]-	231.4	32859911
AllCCS	[M+Na-2H]-	234.6	32859911
AllCCS	[M+HCOO]-	238.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.33 minutes	32390414
Predicted by Siyang on May 30, 2022	30.6399 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4942.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	616.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	377.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	302.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1422.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1328.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2903.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1125.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1611.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	971.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	725.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	188.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	573.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol	COC1=C(O)C(O)=C(C)C(C\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CCC=C(C)C)=C1O	5990.2	Standard polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol	COC1=C(O)C(O)=C(C)C(C\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CCC=C(C)C)=C1O	3981.0	Standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol	COC1=C(O)C(O)=C(C)C(C\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CCC=C(C)C)=C1O	4275.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,isomer #1	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O)=C1O[Si](C)(C)C	4101.3	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,isomer #2	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O[Si](C)(C)C)=C1O	4091.3	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,isomer #3	COC1=C(O)C(O)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C	4188.1	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(O)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C	4107.4	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #2	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	4098.5	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TMS,isomer #3	COC1=C(O)C(O[Si](C)(C)C)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C	4096.5	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,3TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	4113.5	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #1	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O)=C1O[Si](C)(C)C(C)(C)C	4317.6	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #2	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C1O	4313.4	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #3	COC1=C(O)C(O)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C(C)(C)C	4402.8	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C(C)(C)C	4517.3	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #2	COC1=C(O)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4511.4	Semi standard non polar	33892256
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #3	COC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(C/C=C(/C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CCC=C(C)C)=C1O[Si](C)(C)C(C)(C)C	4522.7	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-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-08ml-2298480000-2cbb61853354b11007ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (1 TMS) - 70eV, Positive	splash10-000i-3147469000-5fdc766ff10e478f5f01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS ("2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-15	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-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Positive-QTOF	splash10-004i-0213090000-4a65137eb42195f434de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Positive-QTOF	splash10-0035-1549230000-463e4c4d13762fa9850a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Positive-QTOF	splash10-0002-3269420000-40341ce89f21aa25ad3d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Negative-QTOF	splash10-004i-0000090000-6ffefbe22ee39bd8d207	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Negative-QTOF	splash10-004i-1000190000-c35bad59002e8ccdf17f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Negative-QTOF	splash10-076r-5200980000-8112877d445f435d22c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Positive-QTOF	splash10-00or-5226590000-6dda2e5d3269dc410c73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Positive-QTOF	splash10-001i-9648220000-9470cbdf01957ebc558f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Positive-QTOF	splash10-0536-9513000000-2ef87b7732dc77930914	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 10V, Negative-QTOF	splash10-004i-0000090000-121478cabf4ee3db57a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 20V, Negative-QTOF	splash10-002b-0610290000-23fcf10e704d6d40fa38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 40V, Negative-QTOF	splash10-004j-1533920000-0d9f372f51b6e522994e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB028803

KNApSAcK ID

Not Available

Chemspider ID

30776599

KEGG Compound ID

Not Available

BioCyc ID

2-HEXAPRENYL-3-METHYL-5-HYDROXY-6-METHOX

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481381

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

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

Showing metabocard for 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol (HMDB0012146)

MOL for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

3D MOL for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

3D SDF for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

3D-SDF for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

PDB for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

3D PDB for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

SMILES for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

INCHI for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

Structure for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

3D Structure for HMDB0012146 (2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes