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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:47:36 UTC

Update Date

2021-09-26 23:01:00 UTC

HMDB ID

HMDB0249880

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid

Description

2-(3,8-dimethylazulen-5-yl)propanoic acid belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Based on a literature review very few articles have been published on 2-(3,8-dimethylazulen-5-yl)propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s)-2-(3,8-dimethylazulen-5-yl)propanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249880
     RDKit          3D
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.1868   -3.0074   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -1.8193   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -2.0671   -0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -1.1903   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    0.1249   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096    0.6647   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.6952   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1222    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778   -1.1139    1.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    0.1804    1.1687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    0.9694    0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451    0.6860    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    1.5652    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.0017    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4592    0.9095    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205   -0.4147    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -0.6297    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805   -2.8025   -0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365   -3.3765    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -3.8683   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -3.0503   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -1.5866   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    1.7345    0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.6925   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1066   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.5723   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    0.1273    2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    2.0127    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    3.5260    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    3.0859    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    3.4544   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283    1.3509    0.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -1.1981    0.2314 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

  Mrv1533004151516522D          

 17 18  0  0  0  0            999 V2000
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843    3.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    3.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249880

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC=C(C)C2=CC=C(C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O2/c1-9-4-6-12(11(3)15(16)17)8-14-10(2)5-7-13(9)14/h4-8,11H,1-3H3,(H,16,17)

> <INCHI_KEY>
VEHBLYQIKWPOQM-UHFFFAOYSA-N

> <FORMULA>
C15H16O2

> <MOLECULAR_WEIGHT>
228.291

> <EXACT_MASS>
228.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.960814848796208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,8-dimethylazulen-5-yl)propanoic acid

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
4.170299919

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.788063891280044

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.4727

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,8-dimethylazulen-5-yl)propanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249880
     RDKit          3D
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.1868   -3.0074   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -1.8193   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -2.0671   -0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -1.1903   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    0.1249   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096    0.6647   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.6952   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1222    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778   -1.1139    1.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    0.1804    1.1687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    0.9694    0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451    0.6860    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    1.5652    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.0017    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4592    0.9095    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205   -0.4147    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -0.6297    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805   -2.8025   -0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365   -3.3765    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -3.8683   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -3.0503   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -1.5866   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    1.7345    0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.6925   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1066   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.5723   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    0.1273    2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    2.0127    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    3.5260    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    3.0859    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    3.4544   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283    1.3509    0.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -1.1981    0.2314 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      10.243   4.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.720   4.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.157   5.949   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.117   7.153   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.634   6.178   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.916  -1.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   1.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.114   4.634   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.054   2.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   3.654   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17                                                  
CONECT   17   16    6                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0249880
HETATM    1  C1  UNL     1      -2.187  -3.007  -0.303  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.298  -1.819  -0.339  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.004  -2.067  -0.716  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.084  -1.190  -0.668  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.156   0.125  -0.257  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.510   0.665  -0.104  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.273   0.695  -1.423  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.327  -0.122   0.854  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.778  -1.114   1.393  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.625   0.180   1.169  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.098   0.969   0.019  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.245   0.686   0.180  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.244   1.565   0.530  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.056   3.002   0.802  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.459   0.909   0.592  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.220  -0.415   0.274  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.899  -0.630   0.011  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.181  -2.803  -0.786  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.336  -3.376   0.747  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.757  -3.868  -0.857  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.199  -3.050  -1.087  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.027  -1.587  -1.004  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.462   1.735   0.231  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.150   1.693  -1.925  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.967  -0.107  -2.103  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.351   0.572  -1.210  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.987   0.127   2.112  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.351   2.013   0.127  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.028   3.526   0.917  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.537   3.086   1.781  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.505   3.454  -0.030  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.428   1.351   0.844  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.967  -1.198   0.231  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   11
CONECT    6    7    8   23
CONECT    7   24   25   26
CONECT    8    9    9   10
CONECT   10   27
CONECT   11   12   12   28
CONECT   12   13   17
CONECT   13   14   15   15
CONECT   14   29   30   31
CONECT   15   16   32
CONECT   16   17   17   33
END

HMDB0249880
     RDKit          3D
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.1868   -3.0074   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -1.8193   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -2.0671   -0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -1.1903   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    0.1249   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096    0.6647   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.6952   -1.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1222    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778   -1.1139    1.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    0.1804    1.1687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    0.9694    0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451    0.6860    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    1.5652    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.0017    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4592    0.9095    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205   -0.4147    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -0.6297    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805   -2.8025   -0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365   -3.3765    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -3.8683   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -3.0503   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -1.5866   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    1.7345    0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.6925   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1066   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.5723   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    0.1273    2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    2.0127    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    3.5260    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    3.0859    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    3.4544   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283    1.3509    0.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -1.1981    0.2314 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17  2  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,8-Dimethylazulen-5-yl)propanoate	Generator
Chamazulenecarboxylate	Generator

Chemical Formula

C₁₅H₁₆O₂

Average Molecular Weight

228.291

Monoisotopic Molecular Weight

228.115029755

IUPAC Name

2-(3,8-dimethylazulen-5-yl)propanoic acid

Traditional Name

2-(3,8-dimethylazulen-5-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)=O)C1=CC=C(C)C2=CC=C(C)C2=C1

InChI Identifier

InChI=1S/C15H16O2/c1-9-4-6-12(11(3)15(16)17)8-14-10(2)5-7-13(9)14/h4-8,11H,1-3H3,(H,16,17)

InChI Key

VEHBLYQIKWPOQM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Azulene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	3.69	ALOGPS
logP	4.17	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.47 m³·mol⁻¹	ChemAxon
Polarizability	25.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	157.379	30932474
DeepCCS	[M-H]-	155.016	30932474
DeepCCS	[M-2H]-	187.902	30932474
DeepCCS	[M+Na]+	163.467	30932474
AllCCS	[M+H]+	149.5	32859911
AllCCS	[M+H-H2O]+	145.5	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid	CC(C(O)=O)C1=CC=C(C)C2=CC=C(C)C2=C1	3410.2	Standard polar	33892256
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid	CC(C(O)=O)C1=CC=C(C)C2=CC=C(C)C2=C1	1776.5	Standard non polar	33892256
(2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid	CC(C(O)=O)C1=CC=C(C)C2=CC=C(C)C2=C1	2185.1	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 - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2930000000-6722e417bb37bb696f13	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 10V, Positive-QTOF	splash10-004i-0390000000-9e64c6fabb055ab3553b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 20V, Positive-QTOF	splash10-001i-0930000000-0dfe12962d1b438ca36b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 40V, Positive-QTOF	splash10-0gbc-2900000000-ef56e6bd97909563ff60	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 10V, Negative-QTOF	splash10-0059-0590000000-fb64156336b45cf8255d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 20V, Negative-QTOF	splash10-0a7i-0910000000-e2b0501a8596d1c53dd0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid 40V, Negative-QTOF	splash10-0a4i-0900000000-14b9696996010e6243c8	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8140193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9964600

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid (HMDB0249880)

MOL for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

3D MOL for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

3D SDF for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

3D-SDF for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

PDB for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

3D PDB for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

SMILES for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

INCHI for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

Structure for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

3D Structure for HMDB0249880 ((2S)-2-(3,8-Dimethylazulen-5-yl)propanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra