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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:58:12 UTC

Update Date

2022-03-07 03:17:44 UTC

HMDB ID

HMDB0060380

Secondary Accession Numbers

HMDB60380

Metabolite Identification

Common Name

3-Polyprenyl-4,5-dihydroxybenzoate

Description

3-Polyprenyl-4,5-dihydroxybenzoate, also known as 3,4-dihydroxy-5-polyprenylbenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Polyprenyl-4,5-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid.

Structure

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

HMDB0060380
     RDKit          3D
3-Polyprenyl-4,5-dihydroxybenzoate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.4579   -1.5654   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -0.5911   -0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8246   -0.7165   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    0.3635    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403    0.5215    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713    1.8821    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    2.0898    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    3.4028   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    1.1941    0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    1.2972    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.1902    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.8201    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -1.8843    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544   -2.9202    1.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.8338    3.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -3.9888    1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -1.9843   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -1.0183   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259   -1.1281   -2.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.0509   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296    0.9751   -1.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -2.2443   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420   -0.9672   -1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -2.1016   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4082    0.1368   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620   -0.6914   -1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2121   -1.6542   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0519    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    0.3659    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.2259   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    2.0549   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5141    2.6604    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593    3.7539    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    3.4449   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401    4.2188    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    0.2478    1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.3096    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624    2.2482    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.7153    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6031   -3.9545    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6657   -2.8284   -0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -0.4048   -3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.7782   -1.3866 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  1  0
 18 20  2  0
 20 21  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  1  0
M  END


  Mrv0541 05161317582D          

 21 21  0  0  0  0            999 V2000
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    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    4.9500    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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   -0.4125    0.0000 O   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
    2.8579    0.0000    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
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  2  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  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
 16 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  2  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060380

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-11(2)5-4-6-12(3)7-8-13-9-14(17(20)21)10-15(18)16(13)19/h5,7,9-10,18-19H,4,6,8H2,1-3H3,(H,20,21)/b12-7+

> <INCHI_KEY>
GJZLZMVQYJZMIO-KPKJPENVSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.3542

> <EXACT_MASS>
290.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.3683678581129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
4.411979355000001

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.279265526650002

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.128167445845988

> <JCHEM_PKA_STRONGEST_BASIC>
-6.349574389344849

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
85.32139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.04e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060380
     RDKit          3D
3-Polyprenyl-4,5-dihydroxybenzoate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.4579   -1.5654   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -0.5911   -0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8246   -0.7165   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    0.3635    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403    0.5215    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713    1.8821    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    2.0898    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    3.4028   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    1.1941    0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    1.2972    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.1902    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.8201    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -1.8843    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544   -2.9202    1.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.8338    3.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -3.9888    1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -1.9843   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -1.0183   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259   -1.1281   -2.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.0509   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296    0.9751   -1.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -2.2443   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420   -0.9672   -1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -2.1016   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4082    0.1368   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620   -0.6914   -1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2121   -1.6542   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0519    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    0.3659    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.2259   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    2.0549   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5141    2.6604    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593    3.7539    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    3.4449   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401    4.2188    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    0.2478    1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.3096    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624    2.2482    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.7153    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6031   -3.9545    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6657   -2.8284   -0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -0.4048   -3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.7782   -1.3866 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  1  0
 18 20  2  0
 20 21  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  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      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4   11                                                       
CONECT    6    4   12                                                       
CONECT    7    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9   13   14                                                       
CONECT   10   14   15                                                       
CONECT   11    1    2    5                                                  
CONECT   12    3    6    7                                                  
CONECT   13    8    9   16                                                  
CONECT   14    9   10   17                                                  
CONECT   15   10   16   18                                                  
CONECT   16   13   15   19                                                  
CONECT   17   14   20   21                                                  
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0060380
HETATM    1  C1  UNL     1      -3.458  -1.565  -1.166  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.374  -0.591  -0.515  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.825  -0.717  -0.759  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.894   0.364   0.263  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.440   0.521   0.532  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.971   1.882   0.065  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.524   2.090   0.309  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.047   3.403  -0.080  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.264   1.194   0.866  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.697   1.297   1.148  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.519   0.190   0.614  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.957  -0.820   1.481  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.713  -1.884   1.065  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.154  -2.920   1.989  1.00  0.00           C  
HETATM   15  O1  UNL     1       3.833  -2.834   3.205  1.00  0.00           O  
HETATM   16  O2  UNL     1       4.909  -3.989   1.586  1.00  0.00           O  
HETATM   17  C15 UNL     1       4.070  -1.984  -0.268  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.662  -1.018  -1.144  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.026  -1.128  -2.478  1.00  0.00           O  
HETATM   20  C17 UNL     1       2.896   0.051  -0.698  1.00  0.00           C  
HETATM   21  O4  UNL     1       2.530   0.975  -1.633  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.977  -2.244  -1.848  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.742  -0.967  -1.788  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.858  -2.102  -0.400  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.408   0.137  -0.358  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.962  -0.691  -1.874  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.212  -1.654  -0.326  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.590   1.052   0.719  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.294   0.366   1.605  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.892  -0.226  -0.089  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.183   2.055  -0.999  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.514   2.660   0.653  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.859   3.754   0.579  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.307   3.445  -1.167  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.740   4.219   0.014  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.220   0.248   1.156  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.843   1.310   2.268  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.162   2.248   0.814  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.663  -0.715   2.512  1.00  0.00           H  
HETATM   40  H19 UNL     1       5.603  -3.955   0.840  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.666  -2.828  -0.582  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.715  -0.405  -3.109  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.983   1.778  -1.387  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    4
CONECT    3   25   26   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    9    9
CONECT    8   33   34   35
CONECT    9   10   36
CONECT   10   11   37   38
CONECT   11   12   12   20
CONECT   12   13   39
CONECT   13   14   17   17
CONECT   14   15   15   16
CONECT   16   40
CONECT   17   18   41
CONECT   18   19   20   20
CONECT   19   42
CONECT   20   21
CONECT   21   43
END

HMDB0060380
     RDKit          3D
3-Polyprenyl-4,5-dihydroxybenzoate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.4579   -1.5654   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3737   -0.5911   -0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8246   -0.7165   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    0.3635    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403    0.5215    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713    1.8821    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    2.0898    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    3.4028   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    1.1941    0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    1.2972    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.1902    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.8201    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -1.8843    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544   -2.9202    1.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -2.8338    3.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -3.9888    1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -1.9843   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -1.0183   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259   -1.1281   -2.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    0.0509   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296    0.9751   -1.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771   -2.2443   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420   -0.9672   -1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -2.1016   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4082    0.1368   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620   -0.6914   -1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2121   -1.6542   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0519    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    0.3659    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.2259   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    2.0549   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5141    2.6604    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593    3.7539    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    3.4449   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401    4.2188    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    0.2478    1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.3096    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624    2.2482    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -0.7153    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6031   -3.9545    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6657   -2.8284   -0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -0.4048   -3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    1.7782   -1.3866 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  1  0
 18 20  2  0
 20 21  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dihydroxy-5-polyprenylbenzoate	Kegg
3,4-Dihydroxy-5-polyprenylbenzoic acid	Generator
3-Polyprenyl-4,5-dihydroxybenzoic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Molecular Weight

290.3542

Monoisotopic Molecular Weight

290.151809192

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H22O4/c1-11(2)5-4-6-12(3)7-8-13-9-14(17(20)21)10-15(18)16(13)19/h5,7,9-10,18-19H,4,6,8H2,1-3H3,(H,20,21)/b12-7+

InChI Key

GJZLZMVQYJZMIO-KPKJPENVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Aromatic monoterpenoid
Monoterpenoid
Monocyclic monoterpenoid
Hydroxybenzoic acid
Benzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.06 g/L	ALOGPS
logP	3.95	ALOGPS
logP	4.41	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.32 m³·mol⁻¹	ChemAxon
Polarizability	32.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.442	30932474
DeepCCS	[M-H]-	169.084	30932474
DeepCCS	[M-2H]-	201.97	30932474
DeepCCS	[M+Na]+	177.535	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	171.9	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	172.4	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	8.22 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4156 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2478.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	304.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	647.2 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	607.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1269.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	584.0 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	1240.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	252.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	251.3 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Polyprenyl-4,5-dihydroxybenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	3966.8	Standard polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	2405.6	Standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate	CC(C)=CCC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	2524.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Polyprenyl-4,5-dihydroxybenzoate,1TMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O	2561.2	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,1TMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C	2577.7	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,1TMS,isomer #3	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O	2545.2	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	2517.4	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2551.4	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TMS,isomer #3	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	2501.6	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,3TMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2504.3	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	2808.3	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	2820.1	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,1TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	2805.1	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	2994.5	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3029.3	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,2TBDMS,isomer #3	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	2981.1	Semi standard non polar	33892256
3-Polyprenyl-4,5-dihydroxybenzoate,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3176.0	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-4,5-dihydroxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-069r-7690000000-015b7d2d0b422f0695b3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2000900000-8eec93847eca30d4d05f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 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-4,5-dihydroxybenzoate 10V, Positive-QTOF	splash10-006x-0190000000-df8776d38c479074a0e9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 20V, Positive-QTOF	splash10-00di-5970000000-abb0cc8ad1c8ffce718b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 40V, Positive-QTOF	splash10-066r-8910000000-f4696c464c172ebc4c08	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 10V, Negative-QTOF	splash10-000i-0090000000-29ee0071a876ba3bdc70	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 20V, Negative-QTOF	splash10-000b-0090000000-f296cbae1d1d88253fdc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Polyprenyl-4,5-dihydroxybenzoate 40V, Negative-QTOF	splash10-0ar0-2790000000-cd1cccdccd796d34a0d2	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C17554

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173940

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-4,5-dihydroxybenzoate (HMDB0060380)

MOL for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

3D MOL for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

3D SDF for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

3D-SDF for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

PDB for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

3D PDB for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

SMILES for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

INCHI for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

Structure for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

3D Structure for HMDB0060380 (3-Polyprenyl-4,5-dihydroxybenzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions