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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:58:08 UTC

Update Date

2022-03-07 03:17:44 UTC

HMDB ID

HMDB0060379

Secondary Accession Numbers

HMDB60379

Metabolite Identification

Common Name

3-Polyprenyl-4-hydroxy-5-methoxybenzoate

Description

3-Polyprenyl-4-hydroxy-5-methoxybenzoate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 3-Polyprenyl-4-hydroxy-5-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060379
     RDKit          3D
3-Polyprenyl-4-hydroxy-5-methoxybenzoate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -5.8041    0.8195    1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6176    1.1977    1.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205    0.4361    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.8586    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4328   -1.6872   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589   -3.0423   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9236   -3.4625   -0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472   -3.9246   -1.7143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550   -1.1777   -1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.1186   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6008    0.6408   -1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.6540   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353    1.6941   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    2.9893   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702    1.6644    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458    0.3172    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752   -0.5167    0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.0420    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080   -0.7582    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642   -1.8786   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    0.9057   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734    2.2041    0.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382    1.3971    2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6261    0.8922    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964   -0.2426    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1018   -1.2822    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -3.8267   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609   -1.8487   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -0.0191   -2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.6410   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -0.2991   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    3.6750   -0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    3.5027   -0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.8815   -1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    2.2230    0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    2.2642    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5085    0.3802    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.1724    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.7301   -0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7885   -1.1805    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996    0.3249    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -1.2590    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -2.8903   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592   -1.9747   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.5141   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    2.7646    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  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  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  END


  Mrv0541 05161317582D          

 22 22  0  0  0  0            999 V2000
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    0.7145    2.0625    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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    0.0000    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
    2.1434   -0.4125    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
 22  4  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060379

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O4/c1-12(2)6-5-7-13(3)8-9-14-10-15(18(20)21)11-16(22-4)17(14)19/h6,8,10-11,19H,5,7,9H2,1-4H3,(H,20,21)/b13-8+

> <INCHI_KEY>
HKFHKFTYNQVIHQ-MDWZMJQESA-N

> <FORMULA>
C18H24O4

> <MOLECULAR_WEIGHT>
304.3808

> <EXACT_MASS>
304.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.39087733124019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxy-5-methoxybenzoic acid

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
4.557873411

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.94973344142635

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.123354778746248

> <JCHEM_PKA_STRONGEST_BASIC>
-4.903048193311705

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
89.80369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxy-5-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060379
     RDKit          3D
3-Polyprenyl-4-hydroxy-5-methoxybenzoate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -5.8041    0.8195    1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6176    1.1977    1.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205    0.4361    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.8586    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4328   -1.6872   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589   -3.0423   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9236   -3.4625   -0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472   -3.9246   -1.7143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550   -1.1777   -1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.1186   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6008    0.6408   -1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.6540   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353    1.6941   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    2.9893   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702    1.6644    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458    0.3172    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752   -0.5167    0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.0420    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080   -0.7582    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642   -1.8786   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    0.9057   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734    2.2041    0.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382    1.3971    2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6261    0.8922    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964   -0.2426    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1018   -1.2822    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -3.8267   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609   -1.8487   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -0.0191   -2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.6410   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -0.2991   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    3.6750   -0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    3.5027   -0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.8815   -1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    2.2230    0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    2.2642    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5085    0.3802    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.1724    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.7301   -0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7885   -1.1805    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996    0.3249    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -1.2590    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -2.8903   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592   -1.9747   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.5141   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    2.7646    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  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  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   22                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   13                                                       
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10   14   15                                                       
CONECT   11   15   16                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    7    8                                                  
CONECT   14    9   10   17                                                  
CONECT   15   10   11   18                                                  
CONECT   16   11   17   22                                                  
CONECT   17   14   16   19                                                  
CONECT   18   15   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    4   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0060379
HETATM    1  C1  UNL     1      -5.804   0.819   1.847  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.618   1.198   1.234  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.820   0.436   0.425  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.181  -0.859   0.146  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.433  -1.687  -0.658  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.859  -3.042  -0.915  1.00  0.00           C  
HETATM    7  O2  UNL     1      -4.924  -3.463  -0.398  1.00  0.00           O  
HETATM    8  O3  UNL     1      -3.147  -3.925  -1.714  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.255  -1.178  -1.210  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.862   0.119  -0.952  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.601   0.641  -1.532  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.504   0.654  -0.550  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.235   1.694  -0.197  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.887   2.989  -0.878  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.370   1.664   0.760  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.746   0.317   1.271  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.275  -0.517   0.186  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.514  -1.042   0.319  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.308  -0.758   1.568  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.064  -1.879  -0.753  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.650   0.906  -0.139  1.00  0.00           C  
HETATM   22  O4  UNL     1      -2.273   2.204   0.131  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.038   1.397   2.766  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.626   0.892   1.090  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.796  -0.243   2.171  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.102  -1.282   0.567  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.151  -3.827  -1.771  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.661  -1.849  -1.853  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.341  -0.019  -2.414  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.778   1.641  -2.014  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.697  -0.299  -0.047  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.775   3.675  -0.716  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.029   3.503  -0.428  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.792   2.881  -1.957  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.250   2.223   0.351  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.049   2.264   1.644  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.508   0.380   2.097  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.858  -0.172   1.754  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.750  -0.730  -0.716  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.789  -1.180   2.434  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.500   0.325   1.687  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.307  -1.259   1.478  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.577  -2.890  -0.685  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.159  -1.975  -0.635  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.837  -1.514  -1.777  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.859   2.765   0.724  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   27
CONECT    9   10   28
CONECT   10   11   21   21
CONECT   11   12   29   30
CONECT   12   13   13   31
CONECT   13   14   15
CONECT   14   32   33   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40   41   42
CONECT   20   43   44   45
CONECT   21   22
CONECT   22   46
END

HMDB0060379
     RDKit          3D
3-Polyprenyl-4-hydroxy-5-methoxybenzoate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -5.8041    0.8195    1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6176    1.1977    1.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205    0.4361    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.8586    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4328   -1.6872   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589   -3.0423   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9236   -3.4625   -0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472   -3.9246   -1.7143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550   -1.1777   -1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.1186   -0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6008    0.6408   -1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.6540   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353    1.6941   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    2.9893   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702    1.6644    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458    0.3172    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752   -0.5167    0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.0420    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080   -0.7582    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642   -1.8786   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    0.9057   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734    2.2041    0.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0382    1.3971    2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6261    0.8922    1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964   -0.2426    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1018   -1.2822    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -3.8267   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609   -1.8487   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -0.0191   -2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.6410   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -0.2991   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    3.6750   -0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    3.5027   -0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.8815   -1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    2.2230    0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    2.2642    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5085    0.3802    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.1724    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -0.7301   -0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7885   -1.1805    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996    0.3249    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -1.2590    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767   -2.8903   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592   -1.9747   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.5141   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    2.7646    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  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  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Polyprenyl-4-hydroxy-5-methoxybenzoic acid	Generator

Chemical Formula

C₁₈H₂₄O₄

Average Molecular Weight

304.3808

Monoisotopic Molecular Weight

304.167459256

IUPAC Name

3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxy-5-methoxybenzoic acid

Traditional Name

3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxy-5-methoxybenzoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H24O4/c1-12(2)6-5-7-13(3)8-9-14-10-15(18(20)21)11-16(22-4)17(14)19/h6,8,10-11,19H,5,7,9H2,1-4H3,(H,20,21)/b13-8+

InChI Key

HKFHKFTYNQVIHQ-MDWZMJQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
Aromatic monoterpenoid
Hydroxybenzoic acid
Methoxyphenol
Monocyclic monoterpenoid
Monoterpenoid
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060379)

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	0.0098 g/L	ALOGPS
logP	4.1	ALOGPS
logP	4.56	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	89.8 m³·mol⁻¹	ChemAxon
Polarizability	34.39 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
DarkChem	[M+H]+	175.182	31661259
DarkChem	[M-H]-	176.877	31661259
DeepCCS	[M+H]+	178.482	30932474
DeepCCS	[M-H]-	176.124	30932474
DeepCCS	[M-2H]-	209.011	30932474
DeepCCS	[M+Na]+	184.576	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.9	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Polyprenyl-4-hydroxy-5-methoxybenzoate	COC1=C(O)C(C\C=C(/C)CCC=C(C)C)=CC(=C1)C(O)=O	4021.1	Standard polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate	COC1=C(O)C(C\C=C(/C)CCC=C(C)C)=CC(=C1)C(O)=O	2388.7	Standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate	COC1=C(O)C(C\C=C(/C)CCC=C(C)C)=CC(=C1)C(O)=O	2497.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,1TMS,isomer #1	COC1=CC(C(=O)O)=CC(C/C=C(\C)CCC=C(C)C)=C1O[Si](C)(C)C	2560.7	Semi standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,1TMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C)=CC(C/C=C(\C)CCC=C(C)C)=C1O	2516.2	Semi standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,2TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC(C/C=C(\C)CCC=C(C)C)=C1O[Si](C)(C)C	2510.6	Semi standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,1TBDMS,isomer #1	COC1=CC(C(=O)O)=CC(C/C=C(\C)CCC=C(C)C)=C1O[Si](C)(C)C(C)(C)C	2789.8	Semi standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,1TBDMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C/C=C(\C)CCC=C(C)C)=C1O	2752.8	Semi standard non polar	33892256
3-Polyprenyl-4-hydroxy-5-methoxybenzoate,2TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C/C=C(\C)CCC=C(C)C)=C1O[Si](C)(C)C(C)(C)C	2956.7	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 - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-5490000000-d9b74e85ee0e5354702f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate GC-MS (2 TMS) - 70eV, Positive	splash10-001i-4009600000-acfc55d97d99b4d3441b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 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 - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 10V, Positive-QTOF	splash10-0a4r-0395000000-a63cd9232b7bebd5c3e0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 20V, Positive-QTOF	splash10-0a4r-5971000000-fa5536061737d6866272	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 40V, Positive-QTOF	splash10-0670-8910000000-e41d2b1f432b2eda9828	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 10V, Negative-QTOF	splash10-0udi-0049000000-cb5c1f61c9820647860e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 20V, Negative-QTOF	splash10-0pbc-0093000000-16553ded0805e79acc21	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 40V, Negative-QTOF	splash10-0006-2290000000-6ede795bce2199f61dba	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 10V, Positive-QTOF	splash10-0a4i-1249000000-5a37926385a2541272ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 20V, Positive-QTOF	splash10-0019-3920000000-59f32c5358760a32cdcb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 40V, Positive-QTOF	splash10-0043-5910000000-d0ed5ce53b2d319a2403	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 10V, Negative-QTOF	splash10-0udi-0009000000-12e99b91d9d753973f27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 20V, Negative-QTOF	splash10-0udi-0689000000-40c6438db90b7b536060	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4-hydroxy-5-methoxybenzoate 40V, Negative-QTOF	splash10-0006-1790000000-ed39a44d2bfc91ff118d	2021-10-12	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

C17559

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173941

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 ]

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

3-Polyprenyl-4,5-dihydroxybenzoate + S-Adenosylmethionine → 3-Polyprenyl-4-hydroxy-5-methoxybenzoate + S-Adenosylhomocysteine	details

Showing metabocard for 3-Polyprenyl-4-hydroxy-5-methoxybenzoate (HMDB0060379)

MOL for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

3D MOL for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

3D SDF for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

3D-SDF for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

PDB for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

3D PDB for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

SMILES for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

INCHI for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

Structure for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

3D Structure for HMDB0060379 (3-Polyprenyl-4-hydroxy-5-methoxybenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions