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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:31 UTC

Update Date

2023-02-21 17:20:35 UTC

HMDB ID

HMDB0031469

Secondary Accession Numbers

HMDB31469

Metabolite Identification

Common Name

trans-Isoasarone

Description

trans-Isoasarone, also known as asarone or cis-isoelemicin, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. trans-Isoasarone is found, on average, in the highest concentration within wild carrots (Daucus carota) and carrots (Daucus carota ssp. sativus). This could make trans-isoasarone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on trans-Isoasarone.

Structure

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

HMDB0031469
     RDKit          3D
trans-Isoasarone
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.6042    2.7396    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.1361    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9999    1.0428    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    0.3815    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    0.8845    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416    0.2487    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    0.7997    1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9341    1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8932   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868   -1.5574   -0.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -2.7355   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -1.4161   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -0.7734   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -1.2734   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748   -2.4240   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    3.7913    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0576    2.6636    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    2.2324    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609    2.6226    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.6202   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3433    1.7867    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    2.8707    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804    1.8064    2.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451    2.1359    2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -3.5383   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -2.5222   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -3.0292   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.3182   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -2.3874   -2.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -3.3213   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -2.5071   -2.8490 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
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv0541 02241221152D          

 15 15  0  0  0  0            999 V2000
   -0.6192    1.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    0.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097    1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -0.5225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -0.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2388    1.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533    2.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337    0.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031469

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C(\C=C\C)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

> <INCHI_KEY>
RKFAZBXYICVSKP-AATRIKPKSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.2536

> <EXACT_MASS>
208.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.23765432136439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.623569081666666

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.395374135558071

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
60.80740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asarone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031469
     RDKit          3D
trans-Isoasarone
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.6042    2.7396    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.1361    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9999    1.0428    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    0.3815    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    0.8845    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416    0.2487    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    0.7997    1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9341    1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8932   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868   -1.5574   -0.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -2.7355   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -1.4161   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -0.7734   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -1.2734   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748   -2.4240   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    3.7913    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0576    2.6636    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    2.2324    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609    2.6226    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.6202   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3433    1.7867    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    2.8707    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804    1.8064    2.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451    2.1359    2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -3.5383   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -2.5222   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -3.0292   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.3182   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -2.3874   -2.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -3.3213   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -2.5071   -2.8490 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
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  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  O   UNK     0      -1.156   2.105   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.178   1.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.511   2.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.845   1.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.845  -0.205   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.179  -0.975   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.179  -2.515   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.511  -0.975   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.178  -0.205   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.156  -0.975   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.490  -0.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.179   2.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.179   3.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.513   4.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.490   1.335   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0031469
HETATM    1  C1  UNL     1       3.604   2.740   0.856  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.244   2.136   0.803  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.000   1.043   0.128  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.715   0.382   0.016  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.398   0.884   0.646  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.642   0.249   0.541  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.701   0.800   1.190  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.745   1.934   1.968  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.683  -0.893  -0.220  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.887  -1.557  -0.355  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.027  -2.736  -1.114  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.586  -1.416  -0.859  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.626  -0.773  -0.741  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.736  -1.273  -1.369  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.775  -2.424  -2.157  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.525   3.791   0.548  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.058   2.664   1.860  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.270   2.232   0.155  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.461   2.623   1.336  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.884   0.620  -0.389  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.343   1.787   1.242  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.985   2.871   1.432  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.580   1.806   2.717  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.845   2.136   2.577  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.430  -3.538  -0.621  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.625  -2.522  -2.136  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.083  -3.029  -1.160  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.712  -2.318  -1.436  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.694  -2.387  -2.790  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.783  -3.321  -1.492  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.897  -2.507  -2.849  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   19
CONECT    3    4   20
CONECT    4    5    5   13
CONECT    5    6   21
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   22   23   24
CONECT    9   10   12
CONECT   10   11
CONECT   11   25   26   27
CONECT   12   13   13   28
CONECT   13   14
CONECT   14   15
CONECT   15   29   30   31
END

HMDB0031469
     RDKit          3D
trans-Isoasarone
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.6042    2.7396    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.1361    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9999    1.0428    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    0.3815    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    0.8845    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416    0.2487    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    0.7997    1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9341    1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8932   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868   -1.5574   -0.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -2.7355   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -1.4161   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -0.7734   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -1.2734   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748   -2.4240   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    3.7913    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0576    2.6636    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    2.2324    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609    2.6226    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8838    0.6202   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3433    1.7867    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    2.8707    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804    1.8064    2.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451    2.1359    2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -3.5383   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -2.5222   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -3.0292   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.3182   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -2.3874   -2.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -3.3213   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -2.5071   -2.8490 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
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Asarone	ChEBI
trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene	ChEBI
trans-Isoasaron	ChEBI
Asarone, (e)-isomer	MeSH
Asarone, (Z)-isomer	MeSH
cis-Isoelemicin	MeSH
gamma-Asarone	MeSH
(e)-Asarone	MeSH
(Z)-Asarone	MeSH
Isoasarone	MeSH
2,4,5-Trimethoxypropen-1-ylbenzene	MeSH
beta-Asarone	MeSH
cis-beta-Asarone	MeSH
cis-Isoasarone	MeSH
trans-Asarone	MeSH
trans-Isoasarone	ChEBI
a-Asaron	Generator, HMDB
α-asaron	Generator, HMDB
(e)-2,4,5-Trimethoxypropenylbenzene	HMDB
1,2,4-Trimethoxy-5-(1-propenyl)-(e)-benzene	HMDB
1,2,4-Trimethoxy-5-propenyl-(e)-benzene	HMDB
1,2,4-Trimethoxy-5-propenyl-trans-benzene	HMDB
1,2,4-Trimethoxy-5-[(1E)-1-propenyl]benzene	HMDB
alpha-Asarone	HMDB
Isoasaron (6ci)	HMDB
trans-(alpha )-Asarone	HMDB
trans-2,4,5-Trimethoxypropenylbenzene	HMDB
a-Asarone	Generator
Α-asarone	Generator

Chemical Formula

C₁₂H₁₆O₃

Average Molecular Weight

208.2536

Monoisotopic Molecular Weight

208.109944378

IUPAC Name

1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

Traditional Name

asarone

CAS Registry Number

2883-98-9

SMILES

COC1=CC(OC)=C(\C=C\C)C=C1OC

InChI Identifier

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

InChI Key

RKFAZBXYICVSKP-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Styrene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

asarone (CHEBI:78309 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031469)
Cell membrane (HMDB: HMDB0031469)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031469)

Source

Endogenous

Endogenous (HMDB: HMDB0031469)

Plant

Plant (HMDB: HMDB0031469)

Exogenous

Food

Food (HMDB: HMDB0031469)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Exogenous (HMDB: HMDB0031469)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0031469)

Pesticide (HMDB: HMDB0031469)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antipsychotic (HMDB: HMDB0031469)
Sedative (HMDB: HMDB0031469)

Antipyretic (HMDB: HMDB0031469)
Central nervous system depressant (HMDB: HMDB0031469)

Biological role

Anti bacterial (HMDB: HMDB0031469)
Anti convulsant (HMDB: HMDB0031469)
Anti elleptic (HMDB: HMDB0031469)
Anti spasmodic (HMDB: HMDB0031469)
Bronchospasmolytic (HMDB: HMDB0031469)
Cardiodepressant (HMDB: HMDB0031469)
Emetic (HMDB: HMDB0031469)
Hypothalmic depressant (HMDB: HMDB0031469)
Mutagenic (HMDB: HMDB0031469)
Myorelaxant (HMDB: HMDB0031469)
Psychoactive (HMDB: HMDB0031469)
Secretolytic (HMDB: HMDB0031469)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62 - 63 °C	Not Available
Boiling Point	296.00 to 297.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	101.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.406 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	3.35	ALOGPS
logP	2.62	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.81 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.514	31661259
DarkChem	[M-H]-	150.217	31661259
DeepCCS	[M+H]+	147.231	30932474
DeepCCS	[M-H]-	144.873	30932474
DeepCCS	[M-2H]-	179.686	30932474
DeepCCS	[M+Na]+	154.731	30932474
AllCCS	[M+H]+	146.4	32859911
AllCCS	[M+H-H2O]+	142.3	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.4	32859911
AllCCS	[M-H]-	149.2	32859911
AllCCS	[M+Na-2H]-	149.9	32859911
AllCCS	[M+HCOO]-	150.7	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.	6.61 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0807 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2122.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	419.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	125.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	556.9 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	555.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	451.0 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	1134.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	371.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	492.5 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-Isoasarone	COC1=CC(OC)=C(\C=C\C)C=C1OC	2454.7	Standard polar	33892256
trans-Isoasarone	COC1=CC(OC)=C(\C=C\C)C=C1OC	1622.9	Standard non polar	33892256
trans-Isoasarone	COC1=CC(OC)=C(\C=C\C)C=C1OC	1702.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Isoasarone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mo-1910000000-311a6eeb6d6e7b8cbd71	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Isoasarone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Isoasarone 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 - trans-Isoasarone 10V, Positive-QTOF	splash10-0a4i-0190000000-43c2db0c78cd2c38866d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Positive-QTOF	splash10-0a4i-3890000000-8a310f43dfa83a6852fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Positive-QTOF	splash10-0gvo-5900000000-d8dec13738907307ac30	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Negative-QTOF	splash10-0a4i-0090000000-3260fe63f5df8a57e501	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Negative-QTOF	splash10-0a4m-0930000000-d48f45f13f4ba95211b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Negative-QTOF	splash10-0bt9-3900000000-ee6124b2b2fd1c4c5dc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Positive-QTOF	splash10-0a4i-0090000000-48e778bb33693fbfbece	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Positive-QTOF	splash10-0a4i-0390000000-20df49cd5d736b546ff7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Positive-QTOF	splash10-014i-9500000000-cb4f4e739e22509440dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 10V, Negative-QTOF	splash10-0a4i-0090000000-65fdf834be31e8e78310	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 20V, Negative-QTOF	splash10-0a4i-0980000000-1b5b7322afb6d52db845	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Isoasarone 40V, Negative-QTOF	splash10-0a4i-8900000000-4428ce94cd47e6a5c986	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Asarone

METLIN ID

Not Available

PubChem Compound

636822

PDB ID

Not Available

ChEBI ID

78309

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1290501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gracza L: [Constituents of Asarum europeum L. Communication No. 18. Dynamics of the synthesis of flavonoids]. Acta Pharm Hung. 1991 Mar;61(2):86-90. [PubMed:1887803 ]
(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for trans-Isoasarone (HMDB0031469)

MOL for HMDB0031469 (trans-Isoasarone)

3D MOL for HMDB0031469 (trans-Isoasarone)

3D SDF for HMDB0031469 (trans-Isoasarone)

3D-SDF for HMDB0031469 (trans-Isoasarone)

PDB for HMDB0031469 (trans-Isoasarone)

3D PDB for HMDB0031469 (trans-Isoasarone)

SMILES for HMDB0031469 (trans-Isoasarone)

INCHI for HMDB0031469 (trans-Isoasarone)

Structure for HMDB0031469 (trans-Isoasarone)

3D Structure for HMDB0031469 (trans-Isoasarone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra