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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 02:13:51 UTC

Update Date

2021-09-24 02:13:51 UTC

HMDB ID

HMDB0303482

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Taraxinic acid

Description

Taraxinic acid, also known as taraxinate, belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Taraxinic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Taraxinic acid can be found in dandelion, which makes taraxinic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303482
     RDKit          3D
Taraxinic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0297    3.7040    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    2.5465    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    2.2208    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    2.9645    2.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9168    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.7173    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.4750   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -1.6920   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1525   -2.9020   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -1.8694    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499   -2.2971    0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321   -1.3908    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449   -0.4034    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    0.4738    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721    0.3082    1.5442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    1.5511   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -0.1224   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4653    1.1811   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    1.1895    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832    4.5853    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    3.7808   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    1.5858   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719   -0.4407   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -3.7580   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6245   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1452   -3.1691   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -2.7362    1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.0694    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -2.5891   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -3.2676    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -1.5205    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938    1.5284   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752   -0.9004   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.0987   -1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.0087   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.1432   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.7229    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 02241214262D          

 19 20  0  0  0  0            999 V2000
   -0.6463   -1.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -0.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2794    0.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    0.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -0.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8747   -2.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -1.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -2.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8541    2.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    2.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -1.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 17  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
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303482

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+

> <INCHI_KEY>
KZWCOWFKXMTBRH-IMDCMVKOSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.114242783108267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.007859245666666

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.569612065092144

> <JCHEM_PKA_STRONGEST_BASIC>
-6.874751580755802

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
71.66359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303482
     RDKit          3D
Taraxinic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0297    3.7040    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    2.5465    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    2.2208    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    2.9645    2.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9168    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.7173    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.4750   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -1.6920   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1525   -2.9020   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -1.8694    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499   -2.2971    0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321   -1.3908    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449   -0.4034    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    0.4738    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721    0.3082    1.5442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    1.5511   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -0.1224   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4653    1.1811   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    1.1895    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832    4.5853    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    3.7808   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    1.5858   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719   -0.4407   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -3.7580   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6245   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1452   -3.1691   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -2.7362    1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.0694    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -2.5891   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -3.2676    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -1.5205    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938    1.5284   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752   -0.9004   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.0987   -1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.0087   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.1432   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.7229    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  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      -1.206  -2.928   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.122  -2.563   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.873  -1.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.507   0.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.522   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.853   1.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.242   1.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.813  -0.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.627  -1.666   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.748  -2.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.499  -4.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.531  -0.408   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.386  -1.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.542  -3.040   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.813  -3.761   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.461   3.955   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.008   3.356   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.741   4.204   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.152  -3.707   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    3   12   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    6   16   18                                                  
CONECT   18   17                                                            
CONECT   19    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0303482
HETATM    1  C1  UNL     1       0.030   3.704   0.465  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.488   2.547   0.738  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.508   2.221   1.750  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.902   2.964   2.702  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.999   0.917   1.496  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.657   0.717   0.133  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.027  -0.475  -0.519  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.687  -1.692  -0.165  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.153  -2.902  -0.955  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.828  -1.869   1.033  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.550  -2.297   0.545  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.632  -1.391   0.887  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.945  -0.403   0.064  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.047   0.474   0.471  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.672   0.308   1.544  1.00  0.00           O  
HETATM   16  O4  UNL     1       3.467   1.551  -0.317  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.283  -0.122  -1.203  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.465   1.181  -1.152  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.235   1.190   0.138  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.283   4.585   1.014  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.775   3.781  -0.314  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.211   1.586  -0.368  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.672  -0.441  -1.435  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.495  -3.758  -0.808  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.330  -2.624  -2.003  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.145  -3.169  -0.519  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.325  -2.736   1.582  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.839  -1.069   1.753  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.509  -2.589  -0.526  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.769  -3.268   1.064  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.177  -1.521   1.807  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.294   1.528  -0.880  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.675  -0.900  -1.642  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.095   0.099  -1.959  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.168   2.009  -1.235  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.196   1.143  -2.048  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.425   0.723   0.891  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   13   31
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   16   32
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   37
END

HMDB0303482
     RDKit          3D
Taraxinic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0297    3.7040    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    2.5465    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    2.2208    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    2.9645    2.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9168    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.7173    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.4750   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -1.6920   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1525   -2.9020   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -1.8694    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499   -2.2971    0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321   -1.3908    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449   -0.4034    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    0.4738    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721    0.3082    1.5442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    1.5511   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -0.1224   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4653    1.1811   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    1.1895    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832    4.5853    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    3.7808   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    1.5858   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719   -0.4407   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -3.7580   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6245   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1452   -3.1691   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -2.7362    1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.0694    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -2.5891   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -3.2676    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -1.5205    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938    1.5284   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752   -0.9004   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954    0.0987   -1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.0087   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.1432   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.7229    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylate	Generator
Taraxinate	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Molecular Weight

262.301

Monoisotopic Molecular Weight

262.120509064

IUPAC Name

10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

Traditional Name

10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O

InChI Identifier

InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+

InChI Key

KZWCOWFKXMTBRH-IMDCMVKOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303482)

Food

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.43	ALOGPS
logP	3.01	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-6.9	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	1	ChemAxon
Refractivity	71.66 m³·mol⁻¹	ChemAxon
Polarizability	27.11 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
AllCCS	[M+H]+	161.91	32859911
AllCCS	[M+H-H2O]+	158.203	32859911
AllCCS	[M+Na]+	166.342	32859911
AllCCS	[M+NH4]+	165.352	32859911
AllCCS	[M-H]-	163.994	32859911
AllCCS	[M+Na-2H]-	163.981	32859911
AllCCS	[M+HCOO]-	164.082	32859911
DeepCCS	[M+H]+	167.506	30932474
DeepCCS	[M-H]-	165.148	30932474
DeepCCS	[M-2H]-	198.035	30932474
DeepCCS	[M+Na]+	173.599	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.2575 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1621.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	379.9 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	395.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	800.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	341.0 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	1133.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	200.8 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	87.3 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 10V, Positive-QTOF	splash10-03di-0190000000-ae6142d31796ac852fb6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 20V, Positive-QTOF	splash10-00kb-0790000000-5d35ffc45c3b484e4c04	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 40V, Positive-QTOF	splash10-0fr5-9810000000-c86d11e5f65c79084922	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 10V, Negative-QTOF	splash10-03xr-0090000000-c3b9d93363edbca4028e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 20V, Negative-QTOF	splash10-014i-0290000000-9986126d30d9cb474997	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 40V, Negative-QTOF	splash10-0v4r-6940000000-1491166a575fa1ca8ff7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 10V, Positive-QTOF	splash10-03dj-0090000000-6f75a708aa0bdb1db6aa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 20V, Positive-QTOF	splash10-0292-0190000000-a4afb4679c6c4c570c41	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 40V, Positive-QTOF	splash10-000b-0930000000-cd4fbf1003129ff027d4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 10V, Negative-QTOF	splash10-03di-0090000000-7cbdf4f99e6fc4fe671f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 20V, Negative-QTOF	splash10-014i-0390000000-3b4eeb81d1d38a6936be	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Taraxinic acid 40V, Negative-QTOF	splash10-00kg-3940000000-2b56543ca46b1922f9e7	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB014521

KNApSAcK ID

Not Available

Chemspider ID

59696782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Taraxinic acid (HMDB0303482)

MOL for HMDB0303482 (Taraxinic acid)

3D MOL for HMDB0303482 (Taraxinic acid)

3D SDF for HMDB0303482 (Taraxinic acid)

3D-SDF for HMDB0303482 (Taraxinic acid)

PDB for HMDB0303482 (Taraxinic acid)

3D PDB for HMDB0303482 (Taraxinic acid)

SMILES for HMDB0303482 (Taraxinic acid)

INCHI for HMDB0303482 (Taraxinic acid)

Structure for HMDB0303482 (Taraxinic acid)

3D Structure for HMDB0303482 (Taraxinic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra