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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:58:50 UTC

Update Date

2022-03-07 03:17:44 UTC

HMDB ID

HMDB0060388

Secondary Accession Numbers

HMDB60388

Metabolite Identification

Common Name

4-Hydroxy-3-polyprenylbenzoate

Description

4-Hydroxy-3-polyprenylbenzoate belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 4-Hydroxy-3-polyprenylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060388
     RDKit          3D
4-Hydroxy-3-polyprenylbenzoate
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.8200   -1.3789    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267    0.0742    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3844    0.6271    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.8192   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2858   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453    0.9700    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.4628    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    1.0654    0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4923   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -1.1434   -1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.8163   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5072   -0.0920   -1.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7375    0.2034   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7455    0.9729   -1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.3766   -2.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9667    1.2391   -0.8415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0192   -0.2504    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723   -0.9856    1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -1.2558    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -1.9891    1.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7070   -1.8533    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -1.9029   -0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848   -1.4943    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    1.7390    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790    0.4031   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506    0.3041    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1728    1.8722   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6686   -0.7926   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    0.3639   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5993    2.0616    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    0.8762    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321    0.5651    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525    1.3611    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338    2.0761    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -0.8653   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207   -0.9747   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1525   -2.2968   -1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309    0.2863   -2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2950    2.1981   -0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9803   -0.0476    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.3242    2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -2.2477    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
M  END

  Mrv0541 05161317582D          

 20 20  0  0  0  0            999 V2000
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    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
    0.0000    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
    0.7145    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  3  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060388

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O3/c1-12(2)5-4-6-13(3)7-8-14-11-15(17(19)20)9-10-16(14)18/h5,7,9-11,18H,4,6,8H2,1-3H3,(H,19,20)/b13-7+

> <INCHI_KEY>
HKIMBCGCVPYUTJ-NTUHNPAUSA-N

> <FORMULA>
C17H22O3

> <MOLECULAR_WEIGHT>
274.3548

> <EXACT_MASS>
274.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.460417089042686

> <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-hydroxybenzoic acid

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.715544676666666

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.475161886890266

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.347914248684361

> <JCHEM_PKA_STRONGEST_BASIC>
-6.114865026961756

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
83.34049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-polyprenylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060388
     RDKit          3D
4-Hydroxy-3-polyprenylbenzoate
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.8200   -1.3789    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267    0.0742    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3844    0.6271    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.8192   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2858   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453    0.9700    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.4628    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    1.0654    0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4923   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -1.1434   -1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.8163   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5072   -0.0920   -1.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7375    0.2034   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7455    0.9729   -1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.3766   -2.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9667    1.2391   -0.8415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0192   -0.2504    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723   -0.9856    1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -1.2558    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -1.9891    1.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7070   -1.8533    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -1.9029   -0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848   -1.4943    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    1.7390    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790    0.4031   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506    0.3041    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1728    1.8722   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6686   -0.7926   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    0.3639   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5993    2.0616    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    0.8762    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321    0.5651    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525    1.3611    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338    2.0761    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -0.8653   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207   -0.9747   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1525   -2.2968   -1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309    0.2863   -2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2950    2.1981   -0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9803   -0.0476    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.3242    2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -2.2477    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  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       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   10   15                                                       
CONECT   10    9   16                                                       
CONECT   11   14   15                                                       
CONECT   12    1    2    5                                                  
CONECT   13    3    6    7                                                  
CONECT   14    8   11   16                                                  
CONECT   15    9   11   17                                                  
CONECT   16   10   14   18                                                  
CONECT   17   15   19   20                                                  
CONECT   18   16                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0060388
HETATM    1  C1  UNL     1       4.820  -1.379   0.298  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.027   0.074   0.047  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.384   0.627   0.283  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.013   0.819  -0.370  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.636   0.286  -0.614  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.645   0.970   0.262  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.228   0.463   0.074  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.868   1.065   0.874  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.057  -0.492  -0.777  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.292  -1.143  -1.140  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.562  -0.816  -0.548  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.507  -0.092  -1.236  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.737   0.203  -0.705  1.00  0.00           C  
HETATM   14  C14 UNL     1      -5.746   0.973  -1.433  1.00  0.00           C  
HETATM   15  O1  UNL     1      -5.460   1.377  -2.602  1.00  0.00           O  
HETATM   16  O2  UNL     1      -6.967   1.239  -0.842  1.00  0.00           O  
HETATM   17  C15 UNL     1      -5.019  -0.250   0.568  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.072  -0.986   1.279  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.861  -1.256   0.710  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.934  -1.989   1.434  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.707  -1.853   0.727  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.572  -1.903  -0.663  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.985  -1.494   1.021  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.287   1.739   0.320  1.00  0.00           H  
HETATM   25  H5  UNL     1       7.079   0.403  -0.552  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.851   0.304   1.218  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.173   1.872  -0.549  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.669  -0.793  -0.371  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.378   0.364  -1.697  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.599   2.062   0.071  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.926   0.876   1.349  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.032   0.565   1.851  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.752   1.361   0.323  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.434   2.076   1.206  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.868  -0.865  -1.315  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.421  -0.975  -2.270  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.152  -2.297  -1.152  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.331   0.286  -2.241  1.00  0.00           H  
HETATM   39  H19 UNL     1      -7.295   2.198  -0.877  1.00  0.00           H  
HETATM   40  H20 UNL     1      -5.980  -0.048   1.045  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.346  -1.324   2.289  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.020  -2.248   1.124  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    9    9
CONECT    8   32   33   34
CONECT    9   10   35
CONECT   10   11   36   37
CONECT   11   12   12   19
CONECT   12   13   38
CONECT   13   14   17   17
CONECT   14   15   15   16
CONECT   16   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20
CONECT   20   42
END

HMDB0060388
     RDKit          3D
4-Hydroxy-3-polyprenylbenzoate
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.8200   -1.3789    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267    0.0742    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3844    0.6271    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.8192   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2858   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453    0.9700    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.4628    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    1.0654    0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4923   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -1.1434   -1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.8163   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5072   -0.0920   -1.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7375    0.2034   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7455    0.9729   -1.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604    1.3766   -2.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9667    1.2391   -0.8415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0192   -0.2504    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723   -0.9856    1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -1.2558    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -1.9891    1.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7070   -1.8533    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -1.9029   -0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848   -1.4943    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    1.7390    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790    0.4031   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8506    0.3041    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1728    1.8722   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6686   -0.7926   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    0.3639   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5993    2.0616    0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    0.8762    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321    0.5651    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525    1.3611    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338    2.0761    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -0.8653   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207   -0.9747   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1525   -2.2968   -1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309    0.2863   -2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2950    2.1981   -0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9803   -0.0476    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.3242    2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -2.2477    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3-polyprenylbenzoic acid	Generator

Chemical Formula

C₁₇H₂₂O₃

Average Molecular Weight

274.3548

Monoisotopic Molecular Weight

274.15689457

IUPAC Name

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

Traditional Name

4-hydroxy-3-polyprenylbenzoate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O

InChI Identifier

InChI=1S/C17H22O3/c1-12(2)5-4-6-13(3)7-8-14-11-15(17(19)20)9-10-16(14)18/h5,7,9-11,18H,4,6,8H2,1-3H3,(H,19,20)/b13-7+

InChI Key

HKIMBCGCVPYUTJ-NTUHNPAUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Hydroxybenzoic acid
Monocyclic monoterpenoid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:61122 )
Other Prenol lipids (C05848 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060388)

Source

Exogenous

Exogenous (HMDB: HMDB0060388)

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	0.01 g/L	ALOGPS
logP	4.32	ALOGPS
logP	4.72	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.34 m³·mol⁻¹	ChemAxon
Polarizability	31.46 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]+	170.69	31661259
DarkChem	[M-H]-	168.025	31661259
DeepCCS	[M+H]+	166.645	30932474
DeepCCS	[M-H]-	164.287	30932474
DeepCCS	[M-2H]-	197.173	30932474
DeepCCS	[M+Na]+	172.738	30932474
AllCCS	[M+H]+	167.1	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	169.0	32859911
AllCCS	[M+HCOO]-	169.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-polyprenylbenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O	3645.7	Standard polar	33892256
4-Hydroxy-3-polyprenylbenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O	2235.5	Standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O	2407.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-polyprenylbenzoate,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C	2432.1	Semi standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O	2397.5	Semi standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2382.7	Semi standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2692.0	Semi standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2654.4	Semi standard non polar	33892256
4-Hydroxy-3-polyprenylbenzoate,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2856.2	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 - 4-Hydroxy-3-polyprenylbenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-8980000000-c5f21b9f2315023b8667	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate GC-MS (2 TMS) - 70eV, Positive	splash10-0uk9-8119600000-af4084cfa0588ff40691	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 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 - 4-Hydroxy-3-polyprenylbenzoate 10V, Positive-QTOF	splash10-056r-0290000000-5d0c21c1fa97609e5405	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 20V, Positive-QTOF	splash10-0adi-2950000000-e585e5a13ccaa004bcc8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 40V, Positive-QTOF	splash10-0ldi-8910000000-63c5d4612f9d7c67e790	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 10V, Negative-QTOF	splash10-00di-0090000000-7f80711f214d202e0cb3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 20V, Negative-QTOF	splash10-00b9-0090000000-aa0418550a1f9c60fa4f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 40V, Negative-QTOF	splash10-0nou-3690000000-b3f087074c5c3915fcb4	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 10V, Positive-QTOF	splash10-056r-2590000000-39bbee729d92ce577091	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 20V, Positive-QTOF	splash10-05ar-9800000000-aa69e3364a0f7a35d806	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 40V, Positive-QTOF	splash10-0a59-7900000000-090695f713cd5a105558	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 10V, Negative-QTOF	splash10-00fr-0090000000-b909803416c1dfda8bb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 20V, Negative-QTOF	splash10-05i0-1590000000-789b13156788008d75ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-polyprenylbenzoate 40V, Negative-QTOF	splash10-0900-2920000000-7363aa31358a49cf1043	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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

C00000852

Chemspider ID

Not Available

KEGG Compound ID

C18131

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280844

PDB ID

Not Available

ChEBI ID

61122

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. 4-hydroxybenzoate polyprenyltransferase, mitochondrial

General function:: Involved in prenyltransferase activity
Specific function:: Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:: COQ2
Uniprot ID:: Q96H96
Molecular weight:: 45593.67

Reactions

Geranyl-PP + 4-Hydroxybenzoic acid → 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate	details

Showing metabocard for 4-Hydroxy-3-polyprenylbenzoate (HMDB0060388)

MOL for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

3D MOL for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

3D SDF for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

3D-SDF for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

PDB for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

3D PDB for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

SMILES for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

INCHI for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

Structure for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

3D Structure for HMDB0060388 (4-Hydroxy-3-polyprenylbenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions