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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:34:11 UTC

Update Date

2022-09-22 18:34:24 UTC

HMDB ID

HMDB0030016

Secondary Accession Numbers

HMDB30016

Metabolite Identification

Common Name

Valerenic acid

Description

Valerenic acid, also known as valerenate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Valerenic acid.

Structure

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

HMDB0030016
     RDKit          3D
Valerenic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.2105   -2.4734   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081   -1.7157   -0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -0.5160   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.4483   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342    0.3540    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.1691    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2934    0.0635   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    0.0693    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749    0.1629    2.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543   -0.1253    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.8327   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946    1.8297   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    0.9586   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2414    1.8201    0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.0823    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -1.3335    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -2.2627   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721   -3.4769   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -2.5573   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -1.8953   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953    0.4042   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.4354    1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762    1.0406   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.1857   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674   -0.7543   -1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.2699    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    2.1580    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    2.5318   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3677    1.5045   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7433    2.8824   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.4108   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.3544    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    2.1199    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4513    2.7539    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    0.2888    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8125    1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4635   -1.1992    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -3.3216    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -2.1511   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv0541 02241217312D          

 17 18  0  0  0  0            999 V2000
   -1.7063    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4358    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4358    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754   -0.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -2.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030016

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+

> <INCHI_KEY>
FEBNTWHYQKGEIQ-DHZHZOJOSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.96969461985728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.5963824719999993

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.055677709266172

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.04899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valerenic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030016
     RDKit          3D
Valerenic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.2105   -2.4734   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081   -1.7157   -0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -0.5160   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.4483   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342    0.3540    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.1691    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2934    0.0635   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    0.0693    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749    0.1629    2.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543   -0.1253    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.8327   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946    1.8297   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    0.9586   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2414    1.8201    0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.0823    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -1.3335    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -2.2627   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721   -3.4769   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -2.5573   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -1.8953   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953    0.4042   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.4354    1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762    1.0406   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.1857   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674   -0.7543   -1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.2699    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    2.1580    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    2.5318   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3677    1.5045   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7433    2.8824   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.4108   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.3544    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    2.1199    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4513    2.7539    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    0.2888    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8125    1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4635   -1.1992    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -3.3216    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -2.1511   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.185   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.279   2.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.813   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.813   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.279   0.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.754  -1.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.518   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.518   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.853   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.853   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.518   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.518  -1.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.853  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.185  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.518  -4.617   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.853  -3.847   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.185  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   11                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    4   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   13   15   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0030016
HETATM    1  C1  UNL     1       0.210  -2.473  -1.543  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.708  -1.716  -0.636  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.473  -0.516  -0.183  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.645   0.448  -0.360  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.634   0.354   0.739  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.908   0.169   0.452  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.293   0.064  -0.965  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.929   0.069   1.512  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.575   0.163   2.716  1.00  0.00           O  
HETATM   10  O2  UNL     1       5.254  -0.125   1.156  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.003   1.833  -0.225  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.395   1.830  -0.813  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.363   0.959  -0.068  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.241   1.820   0.798  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.605  -0.082   0.691  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.364  -1.333   0.974  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.004  -2.263  -0.156  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.172  -3.477  -1.791  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.225  -2.557  -1.127  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.257  -1.895  -2.490  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.095   0.404  -1.354  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.317   0.435   1.758  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.176   1.041  -1.499  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.372  -0.186  -1.013  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.767  -0.754  -1.497  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.991   0.270   1.750  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.018   2.158   0.825  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.605   2.532  -0.830  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.368   1.504  -1.859  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.743   2.882  -0.810  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.035   0.411  -0.788  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.224   1.354   1.010  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.701   2.120   1.710  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.451   2.754   0.232  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.201   0.289   1.655  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.063  -1.813   1.931  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.464  -1.199   0.951  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.933  -3.322   0.162  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.727  -2.151  -1.017  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   15
CONECT    4    5   11   21
CONECT    5    6    6   22
CONECT    6    7    8
CONECT    7   23   24   25
CONECT    8    9    9   10
CONECT   10   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   15   31
CONECT   14   32   33   34
CONECT   15   16   35
CONECT   16   17   36   37
CONECT   17   38   39
END

HMDB0030016
     RDKit          3D
Valerenic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.2105   -2.4734   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081   -1.7157   -0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -0.5160   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.4483   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342    0.3540    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.1691    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2934    0.0635   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    0.0693    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749    0.1629    2.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543   -0.1253    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.8327   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946    1.8297   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    0.9586   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2414    1.8201    0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.0823    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -1.3335    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -2.2627   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1721   -3.4769   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -2.5573   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -1.8953   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953    0.4042   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.4354    1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762    1.0406   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.1857   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674   -0.7543   -1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.2699    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    2.1580    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    2.5318   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3677    1.5045   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7433    2.8824   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.4108   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.3544    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    2.1199    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4513    2.7539    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    0.2888    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8125    1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4635   -1.1992    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -3.3216    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -2.1511   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Valerenate	Generator
IMU	HMDB
(2E)-3-(3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoate	Generator

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

(2E)-3-(3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid

Traditional Name

valerenic acid

CAS Registry Number

3569-10-6

SMILES

CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12

InChI Identifier

InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+

InChI Key

FEBNTWHYQKGEIQ-DHZHZOJOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030016)

Source

Endogenous

Endogenous (HMDB: HMDB0030016)

Plant

Plant (HMDB: HMDB0030016)

Animal

Animal (HMDB: HMDB0030016)

Exogenous

Food

Food (HMDB: HMDB0030016)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0030016)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030016)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030016)

Lipid metabolism pathway (HMDB: HMDB0030016)

Cellular process

Cell signaling (HMDB: HMDB0030016)

Biochemical process

Lipid transport (HMDB: HMDB0030016)

Role

Biological role

Energy source (HMDB: HMDB0030016)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030016)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 - 142 °C	Not Available
Boiling Point	374.00 to 375.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	5.188 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	4.15	ALOGPS
logP	3.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	5.06	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.05 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.887	31661259
DarkChem	[M-H]-	155.799	31661259
DeepCCS	[M-2H]-	194.979	30932474
DeepCCS	[M+Na]+	170.544	30932474
AllCCS	[M+H]+	155.5	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	162.3	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.61 minutes	32390414
Predicted by Siyang on May 30, 2022	17.0904 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2525.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	514.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	261.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	639.0 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	728.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1373.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	525.0 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	1435.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	407.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	525.7 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	29.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valerenic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12	3045.8	Standard polar	33892256
Valerenic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12	1836.4	Standard non polar	33892256
Valerenic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12	1815.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valerenic acid,1TMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C)CCC(C)C2CC1	1949.8	Semi standard non polar	33892256
Valerenic acid,1TBDMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C)CCC(C)C2CC1	2167.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-2970000000-faf955331d2d52d6f5bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-004l-2390000000-eabd784d84c1e1c900e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenic acid 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 - Valerenic acid 10V, Positive-QTOF	splash10-00kr-0590000000-a785f5975e2057349881	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 20V, Positive-QTOF	splash10-029i-2920000000-9b5ea2b85cfca509eebd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 40V, Positive-QTOF	splash10-0kas-5900000000-04bd3a0d24cc33998f34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 10V, Negative-QTOF	splash10-001i-0190000000-9bd08037c9a732194f63	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 20V, Negative-QTOF	splash10-03ei-1950000000-0938af4600cdeb8b45f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 40V, Negative-QTOF	splash10-00di-5910000000-8a729ac3d0b2c80cc696	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 10V, Positive-QTOF	splash10-029i-0960000000-5d5a27701726a3e27a37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 20V, Positive-QTOF	splash10-00kk-2920000000-b7acb01868f53a96c0fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 40V, Positive-QTOF	splash10-0006-9300000000-a7d2c0158d2123f483ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 10V, Negative-QTOF	splash10-001i-0490000000-643538f3213444302a70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 20V, Negative-QTOF	splash10-03e9-0950000000-fe98051c5cce95c9f525	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenic acid 40V, Negative-QTOF	splash10-06si-0940000000-c2e4b48bbe96ee5e4d91	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valerenic acid

METLIN ID

Not Available

PubChem Compound

6042891

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1442331

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Valerenic acid (HMDB0030016)

MOL for HMDB0030016 (Valerenic acid)

3D MOL for HMDB0030016 (Valerenic acid)

3D SDF for HMDB0030016 (Valerenic acid)

3D-SDF for HMDB0030016 (Valerenic acid)

PDB for HMDB0030016 (Valerenic acid)

3D PDB for HMDB0030016 (Valerenic acid)

SMILES for HMDB0030016 (Valerenic acid)

INCHI for HMDB0030016 (Valerenic acid)

Structure for HMDB0030016 (Valerenic acid)

3D Structure for HMDB0030016 (Valerenic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra