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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:43:10 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036563

Secondary Accession Numbers

HMDB36563

Metabolite Identification

Common Name

Valerenolic acid

Description

Valerenolic acid, also known as valerenolate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Valerenolic acid.

Structure

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

HMDB0036563
     RDKit          3D
Valerenolic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6606    2.6288    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.2294    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.3457    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.3500   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636   -0.5743    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.1486    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2598    1.2736    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.0671    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.3004    1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.5540    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.1034   -1.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -1.4239   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -1.3408   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -0.4185   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -0.9304    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974   -0.7724    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098   -1.1775    0.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.6776    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272    2.6699    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    3.2871    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341    3.0430    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    1.3916   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -1.6140    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    1.5375   -0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871    1.4848    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9455    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108   -0.1515    2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366   -0.2492   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    0.6439   -2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682   -2.1630   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383   -1.6781   -2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.3751   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -0.3249   -2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5747   -0.9165   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.5899   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -1.7003    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -1.3540    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972   -1.8282    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2974    0.8381    2.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    1.2298    1.1567 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
 16 18  1  0
 18  2  1  0
 15  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061309122D          

 18 19  0  0  0  0            999 V2000
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036563

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-4-5-11(6-10(3)15(17)18)13-9(2)7-12(16)14(8)13/h6,8,11-12,14,16H,4-5,7H2,1-3H3,(H,17,18)/b10-6+

> <INCHI_KEY>
XJNQXTISSHEQKD-UXBLZVDNSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.897795828871295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
2.287617675000001

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.234472361271965

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.877750020411587

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9466425113911193

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.6415

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036563
     RDKit          3D
Valerenolic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6606    2.6288    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.2294    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.3457    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.3500   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636   -0.5743    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.1486    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2598    1.2736    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.0671    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.3004    1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.5540    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.1034   -1.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -1.4239   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -1.3408   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -0.4185   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -0.9304    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974   -0.7724    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098   -1.1775    0.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.6776    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272    2.6699    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    3.2871    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341    3.0430    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    1.3916   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -1.6140    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    1.5375   -0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871    1.4848    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9455    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108   -0.1515    2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366   -0.2492   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    0.6439   -2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682   -2.1630   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383   -1.6781   -2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.3751   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -0.3249   -2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5747   -0.9165   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.5899   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -1.7003    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -1.3540    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972   -1.8282    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2974    0.8381    2.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    1.2298    1.1567 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
 16 18  1  0
 18  2  1  0
 15  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.924   9.003   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6   10   11                                                       
CONECT    7    9   12                                                       
CONECT    8    1    4   14                                                  
CONECT    9    2    7   13                                                  
CONECT   10    3    6   15                                                  
CONECT   11    5    6   13                                                  
CONECT   12    7   14   16                                                  
CONECT   13    9   11   14                                                  
CONECT   14    8   12   13                                                  
CONECT   15   10   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0036563
HETATM    1  C1  UNL     1      -0.661   2.629   1.182  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.128   1.229   0.973  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.483   0.346   0.252  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.788   0.350  -0.541  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.764  -0.574   0.018  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.952  -0.149   0.388  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.260   1.274   0.220  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.932  -1.067   0.947  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.664  -2.300   1.092  1.00  0.00           O  
HETATM   10  O2  UNL     1       5.166  -0.554   1.317  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.423  -0.103  -1.947  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.315  -1.424  -1.927  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.593  -1.341  -1.120  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.561  -0.418  -1.796  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.243  -0.930   0.270  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.397  -0.772   1.186  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.610  -1.178   0.638  1.00  0.00           O  
HETATM   18  C15 UNL     1      -2.380   0.678   1.558  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.227   2.670   1.851  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.455   3.287   1.591  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.334   3.043   0.206  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.112   1.392  -0.602  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.524  -1.614   0.135  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.299   1.538  -0.861  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.287   1.485   0.622  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.584   1.946   0.787  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.211  -0.152   2.266  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.337  -0.249  -2.538  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.251   0.644  -2.409  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.368  -2.163  -1.454  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.538  -1.678  -2.982  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.001  -2.375  -1.076  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.276  -0.325  -2.877  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.575  -0.916  -1.822  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.598   0.590  -1.382  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.561  -1.700   0.690  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.273  -1.354   2.139  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.097  -1.828   1.179  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.297   0.838   2.673  1.00  0.00           H  
HETATM   40  H22 UNL     1      -3.271   1.230   1.157  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   15
CONECT    4    5   11   22
CONECT    5    6    6   23
CONECT    6    7    8
CONECT    7   24   25   26
CONECT    8    9    9   10
CONECT   10   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15   32
CONECT   14   33   34   35
CONECT   15   16   36
CONECT   16   17   18   37
CONECT   17   38
CONECT   18   39   40
END

HMDB0036563
     RDKit          3D
Valerenolic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6606    2.6288    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.2294    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.3457    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.3500   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636   -0.5743    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.1486    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2598    1.2736    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.0671    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.3004    1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.5540    1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.1034   -1.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -1.4239   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -1.3408   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -0.4185   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -0.9304    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974   -0.7724    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098   -1.1775    0.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.6776    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272    2.6699    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    3.2871    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341    3.0430    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    1.3916   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -1.6140    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    1.5375   -0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871    1.4848    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9455    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108   -0.1515    2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366   -0.2492   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    0.6439   -2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682   -2.1630   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383   -1.6781   -2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.3751   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -0.3249   -2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5747   -0.9165   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    0.5899   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -1.7003    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -1.3540    2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972   -1.8282    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2974    0.8381    2.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    1.2298    1.1567 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
 16 18  1  0
 18  2  1  0
 15  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Valerenolate	Generator
Hydroxyvalerenic acid	HMDB
(2E)-3-(1-Hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoate	Generator
Valerenolic acid	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1619-16-5

SMILES

CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(O)C12

InChI Identifier

InChI=1S/C15H22O3/c1-8-4-5-11(6-10(3)15(17)18)13-9(2)7-12(16)14(8)13/h6,8,11-12,14,16H,4-5,7H2,1-3H3,(H,17,18)/b10-6+

InChI Key

XJNQXTISSHEQKD-UXBLZVDNSA-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
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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: HMDB0036563)

Source

Endogenous

Endogenous (HMDB: HMDB0036563)

Plant

Plant (HMDB: HMDB0036563)

Animal

Animal (HMDB: HMDB0036563)

Exogenous

Food

Food (HMDB: HMDB0036563)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0036563)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036563)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036563)

Lipid metabolism pathway (HMDB: HMDB0036563)

Cellular process

Cell signaling (HMDB: HMDB0036563)

Biochemical process

Lipid transport (HMDB: HMDB0036563)

Role

Biological role

Energy source (HMDB: HMDB0036563)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036563)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	426.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	178.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.293 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	1.88	ALOGPS
logP	2.29	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-0.95	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	2	ChemAxon
Refractivity	71.64 m³·mol⁻¹	ChemAxon
Polarizability	27.9 Å³	ChemAxon
Number of Rings	2	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]+	162.137	31661259
DarkChem	[M-H]-	157.673	31661259
DeepCCS	[M-2H]-	202.317	30932474
DeepCCS	[M+Na]+	177.882	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.1	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.56 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4506 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2206.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	292.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	459.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	535.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	966.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.6 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	1236.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	295.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	313.1 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	67.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(O)C12	3430.2	Standard polar	33892256
Valerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(O)C12	1957.8	Standard non polar	33892256
Valerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(O)C12	1997.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valerenolic acid,1TMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C)CCC(C)C2C(O)C1	2104.7	Semi standard non polar	33892256
Valerenolic acid,1TMS,isomer #2	CC1=C2C(/C=C(\C)C(=O)O)CCC(C)C2C(O[Si](C)(C)C)C1	2183.4	Semi standard non polar	33892256
Valerenolic acid,2TMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C)CCC(C)C2C(O[Si](C)(C)C)C1	2168.8	Semi standard non polar	33892256
Valerenolic acid,1TBDMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C)CCC(C)C2C(O)C1	2327.4	Semi standard non polar	33892256
Valerenolic acid,1TBDMS,isomer #2	CC1=C2C(/C=C(\C)C(=O)O)CCC(C)C2C(O[Si](C)(C)C(C)(C)C)C1	2420.5	Semi standard non polar	33892256
Valerenolic acid,2TBDMS,isomer #1	CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C)CCC(C)C2C(O[Si](C)(C)C(C)(C)C)C1	2597.9	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 - Valerenolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-2290000000-fd625bbc5288f95e5448	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3039000000-548cfc54bd2631b327aa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valerenolic 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 - Valerenolic acid 10V, Positive-QTOF	splash10-0f89-0290000000-07c2ecd7550056d2f049	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 20V, Positive-QTOF	splash10-05qi-3960000000-7bc54a1a34169d6efa08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 40V, Positive-QTOF	splash10-000i-6900000000-1eac2aef82e4cb08a8f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 10V, Negative-QTOF	splash10-0002-0090000000-dc1cb0729e06560c5506	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 20V, Negative-QTOF	splash10-055k-1690000000-d221414edc3557d4bb61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 40V, Negative-QTOF	splash10-052r-7950000000-acf4d5e98a0228b8a126	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 10V, Negative-QTOF	splash10-002b-0690000000-0b3c186b3cf54e0fd996	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 20V, Negative-QTOF	splash10-01ua-0960000000-dc023c90143d0b35e056	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 40V, Negative-QTOF	splash10-0012-1930000000-080f110800b916ebb5ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 10V, Positive-QTOF	splash10-0f89-0690000000-6ae01098cabaa8be56bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 20V, Positive-QTOF	splash10-00lb-0940000000-99b9cd4c78ae2e7ef5c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerenolic acid 40V, Positive-QTOF	splash10-0006-9400000000-8f798edfc79b26d3570e	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015467

KNApSAcK ID

C00021291

Chemspider ID

4943985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439586

PDB ID

Not Available

ChEBI ID

174304

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1454651

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 Valerenolic acid (HMDB0036563)

MOL for HMDB0036563 (Valerenolic acid)

3D MOL for HMDB0036563 (Valerenolic acid)

3D SDF for HMDB0036563 (Valerenolic acid)

3D-SDF for HMDB0036563 (Valerenolic acid)

PDB for HMDB0036563 (Valerenolic acid)

3D PDB for HMDB0036563 (Valerenolic acid)

SMILES for HMDB0036563 (Valerenolic acid)

INCHI for HMDB0036563 (Valerenolic acid)

Structure for HMDB0036563 (Valerenolic acid)

3D Structure for HMDB0036563 (Valerenolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra