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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:41:45 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035687

Secondary Accession Numbers

HMDB35687

Metabolite Identification

Common Name

Acetylvalerenolic acid

Description

Acetylvalerenolic acid 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 Acetylvalerenolic acid.

Structure

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

HMDB0035687
     RDKit          3D
Acetylvalerenolic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
   -4.7986    0.0460    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -0.6197    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3721   -1.6827   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -0.1216    0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943   -0.7886   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332    0.2423   -1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.0389   -1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331    2.4495   -1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.2939   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    0.6613    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    0.3531   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544    1.2297   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    2.6444   -0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7846   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884    1.6080   -1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6160   -0.5441   -1.8512 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1298    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8999   -1.5982    1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.6438    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -3.0500    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -1.0440   -0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6086    0.6680    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    0.6824    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188   -0.6960    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -1.6836   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272    0.8458   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.2992   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    2.8912   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.4900   -2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    3.0563   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    1.7292    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -0.6718   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9104    3.2643   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    2.7751    0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    3.0539   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584   -1.2791   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4900    0.2464    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   -0.0804    2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -1.9579    0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837   -2.1560    2.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.0838    1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836   -2.9793    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -3.4988   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -3.7075    1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -1.7390   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END


  Mrv0541 05061308382D          

 21 22  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
   -0.1781   -0.8853    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
    0.0768   -0.1006    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
   -0.4752    0.5124    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
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035687

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-9-5-6-13(7-11(3)17(19)20)15-10(2)8-14(16(9)15)21-12(4)18/h7,9,13-14,16H,5-6,8H2,1-4H3,(H,19,20)/b11-7+

> <INCHI_KEY>
VBBXZFLAYWAXSK-YRNVUSSQSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.14657298619919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.728743085333333

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.550861492932636

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004607469535601

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
80.793

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035687
     RDKit          3D
Acetylvalerenolic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
   -4.7986    0.0460    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -0.6197    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3721   -1.6827   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -0.1216    0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943   -0.7886   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332    0.2423   -1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.0389   -1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331    2.4495   -1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.2939   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    0.6613    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    0.3531   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544    1.2297   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    2.6444   -0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7846   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884    1.6080   -1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6160   -0.5441   -1.8512 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1298    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8999   -1.5982    1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.6438    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -3.0500    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -1.0440   -0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6086    0.6680    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    0.6824    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188   -0.6960    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -1.6836   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272    0.8458   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.2992   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    2.8912   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.4900   -2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    3.0563   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    1.7292    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -0.6718   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9104    3.2643   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    2.7751    0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    3.0539   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584   -1.2791   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4900    0.2464    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   -0.0804    2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -1.9579    0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837   -2.1560    2.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.0838    1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836   -2.9793    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -3.4988   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -3.7075    1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -1.7390   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  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      -0.332  -1.653   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.887   0.956   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.924   9.003   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    9                                                       
CONECT    6    5   13                                                       
CONECT    7   11   13                                                       
CONECT    8   10   14                                                       
CONECT    9    1    5   16                                                  
CONECT   10    2    8   15                                                  
CONECT   11    3    7   17                                                  
CONECT   12    4   18   21                                                  
CONECT   13    6    7   15                                                  
CONECT   14    8   16   21                                                  
CONECT   15   10   13   16                                                  
CONECT   16    9   14   15                                                  
CONECT   17   11   19   20                                                  
CONECT   18   12                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0035687
HETATM    1  C1  UNL     1      -4.799   0.046   1.582  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.991  -0.620   0.533  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.372  -1.683  -0.047  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.755  -0.122   0.113  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.994  -0.789  -0.906  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.733   0.242  -1.976  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.635   1.039  -1.374  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.333   2.449  -1.726  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.028   0.294  -0.476  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.198   0.661   0.372  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.431   0.353  -0.400  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.354   1.230  -0.729  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.197   2.644  -0.319  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.509   0.785  -1.489  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.388   1.608  -1.805  1.00  0.00           O  
HETATM   16  O4  UNL     1       4.616  -0.544  -1.851  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.189  -0.130   1.654  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.900  -1.598   1.399  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.536  -1.644   0.939  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.081  -3.050   0.895  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.585  -1.044  -0.418  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.609   0.668   1.146  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.108   0.682   2.191  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.219  -0.696   2.322  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.504  -1.684  -1.271  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.627   0.846  -2.213  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.359  -0.299  -2.863  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.235   2.891  -2.194  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.559   2.490  -2.382  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.184   3.056  -0.789  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.121   1.729   0.624  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.568  -0.672  -0.710  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.910   3.264  -0.908  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.515   2.775   0.756  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.192   3.054  -0.496  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.658  -1.279  -1.153  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.490   0.246   2.406  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.211  -0.080   2.086  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.523  -1.958   0.550  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.084  -2.156   2.327  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.137  -1.084   1.682  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.184  -2.979   0.998  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.890  -3.499  -0.115  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.664  -3.708   1.674  1.00  0.00           H  
HETATM   45  H24 UNL     1      -0.111  -1.739  -1.137  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   21   25
CONECT    6    7   26   27
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT    9   10   21
CONECT   10   11   17   31
CONECT   11   12   12   32
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   15   15   16
CONECT   16   36
CONECT   17   18   37   38
CONECT   18   19   39   40
CONECT   19   20   21   41
CONECT   20   42   43   44
CONECT   21   45
END

HMDB0035687
     RDKit          3D
Acetylvalerenolic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
   -4.7986    0.0460    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -0.6197    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3721   -1.6827   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -0.1216    0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943   -0.7886   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332    0.2423   -1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    1.0389   -1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331    2.4495   -1.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.2939   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    0.6613    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    0.3531   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544    1.2297   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    2.6444   -0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087    0.7846   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884    1.6080   -1.8045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6160   -0.5441   -1.8512 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1298    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8999   -1.5982    1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365   -1.6438    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -3.0500    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -1.0440   -0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6086    0.6680    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    0.6824    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188   -0.6960    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -1.6836   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272    0.8458   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.2992   -2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    2.8912   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.4900   -2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    3.0563   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    1.7292    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -0.6718   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9104    3.2643   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    2.7751    0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    3.0539   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584   -1.2791   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4900    0.2464    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   -0.0804    2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -1.9579    0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837   -2.1560    2.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.0838    1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836   -2.9793    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -3.4988   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -3.7075    1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -1.7390   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acetylvalerenolate	Generator
Acetoxyvalerenic acid	HMDB
(2E)-3-[1-(Acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoate	Generator
Acetylvalerenolic acid	MeSH

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

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

Traditional Name

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

CAS Registry Number

81397-67-3

SMILES

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

InChI Identifier

InChI=1S/C17H24O4/c1-9-5-6-13(7-11(3)17(19)20)15-10(2)8-14(16(9)15)21-12(4)18/h7,9,13-14,16H,5-6,8H2,1-4H3,(H,19,20)/b11-7+

InChI Key

VBBXZFLAYWAXSK-YRNVUSSQSA-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
Dicarboxylic acid or derivatives
Carboxylic acid ester
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

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035687)

Source

Endogenous

Endogenous (HMDB: HMDB0035687)

Plant

Plant (HMDB: HMDB0035687)

Animal

Animal (HMDB: HMDB0035687)

Exogenous

Food

Food (HMDB: HMDB0035687)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0035687)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035687)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035687)

Lipid metabolism pathway (HMDB: HMDB0035687)

Cellular process

Cell signaling (HMDB: HMDB0035687)

Biochemical process

Lipid transport (HMDB: HMDB0035687)

Role

Biological role

Energy source (HMDB: HMDB0035687)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035687)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	427.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	4.42 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.106 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.73	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.79 m³·mol⁻¹	ChemAxon
Polarizability	32.15 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]+	170.966	31661259
DarkChem	[M-H]-	168.848	31661259
DeepCCS	[M-2H]-	210.677	30932474
DeepCCS	[M+Na]+	186.03	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	175.7	32859911
AllCCS	[M+HCOO]-	176.2	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.	7.15 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2852 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2543.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	122.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	576.5 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	638.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1247.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	522.8 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	1508.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	442.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	305.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.2 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	44.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylvalerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(OC(C)=O)C12	3638.6	Standard polar	33892256
Acetylvalerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(OC(C)=O)C12	2039.7	Standard non polar	33892256
Acetylvalerenolic acid	CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(OC(C)=O)C12	2086.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetylvalerenolic acid,1TMS,isomer #1	CC(=O)OC1CC(C)=C2C(/C=C(\C)C(=O)O[Si](C)(C)C)CCC(C)C21	2239.1	Semi standard non polar	33892256
Acetylvalerenolic acid,1TBDMS,isomer #1	CC(=O)OC1CC(C)=C2C(/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C)CCC(C)C21	2447.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylvalerenolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-2290000000-529a7f8ec9eae9d4f258	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylvalerenolic acid GC-MS (1 TMS) - 70eV, Positive	splash10-056v-4196000000-21f2051cec69d0f86921	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylvalerenolic 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 - Acetylvalerenolic acid 10V, Positive-QTOF	splash10-0006-0090000000-ed8845fdd32ab1b8dc33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 20V, Positive-QTOF	splash10-0uea-0490000000-4f820e61df23116ab3b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 40V, Positive-QTOF	splash10-0khj-2920000000-0cfec4ff6c6899bdf241	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 10V, Negative-QTOF	splash10-0007-1090000000-6506f1685409a1363043	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 20V, Negative-QTOF	splash10-052e-2090000000-dd280e0d094f852bc6a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 40V, Negative-QTOF	splash10-0a4l-7090000000-e2829d1e4755d594246a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 10V, Negative-QTOF	splash10-0a5i-8790000000-75cd8a17a975e1c42429	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 40V, Negative-QTOF	splash10-052f-9630000000-90e3cd7f496fc0b00dab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 10V, Positive-QTOF	splash10-001i-0490000000-22ba0f07b19460e16e4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 20V, Positive-QTOF	splash10-000b-0930000000-2d7ce207c462e83c0815	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylvalerenolic acid 40V, Positive-QTOF	splash10-0006-9610000000-3514d958a46f27deb603	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014404

KNApSAcK ID

C00021292

Chemspider ID

4943984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439585

PDB ID

Not Available

ChEBI ID

172142

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1408781

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 Acetylvalerenolic acid (HMDB0035687)

MOL for HMDB0035687 (Acetylvalerenolic acid)

3D MOL for HMDB0035687 (Acetylvalerenolic acid)

3D SDF for HMDB0035687 (Acetylvalerenolic acid)

3D-SDF for HMDB0035687 (Acetylvalerenolic acid)

PDB for HMDB0035687 (Acetylvalerenolic acid)

3D PDB for HMDB0035687 (Acetylvalerenolic acid)

SMILES for HMDB0035687 (Acetylvalerenolic acid)

INCHI for HMDB0035687 (Acetylvalerenolic acid)

Structure for HMDB0035687 (Acetylvalerenolic acid)

3D Structure for HMDB0035687 (Acetylvalerenolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra