Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:07:23 UTC

Update Date

2022-03-07 02:54:03 UTC

HMDB ID

HMDB0034312

Secondary Accession Numbers

HMDB34312

Metabolite Identification

Common Name

Isopimpinellin

Description

Isopimpinellin belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. Isopimpinellin is found, on average, in the highest concentration within a few different foods, such as parsleys (Petroselinum crispum), celery stalks (Apium graveolens var. dulce), and fennels (Foeniculum vulgare). Isopimpinellin has also been detected, but not quantified in, several different foods, such as parsnips (Pastinaca sativa), limes (Citrus aurantiifolia), wild carrots (Daucus carota), anises (Pimpinella anisum), and lemons (Citrus limon). This could make isopimpinellin a potential biomarker for the consumption of these foods. Isopimpinellin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Isopimpinellin.

Structure

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

HMDB0034312
     RDKit          3D
Isopimpinellin
 28 30  0  0  0  0  0  0  0  0999 V2000
    3.3520    1.1162    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.7271   -0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2284    0.1997   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -1.1507   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268   -2.2192   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -3.3483    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.9872    0.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.6806    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2954   -0.8480    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710   -1.3476    0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185   -1.7153   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1198    0.5108    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    1.3240    0.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639    2.6237    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581    3.3926    0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8276    3.1702   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    2.3837   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    1.0295   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    0.2848    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3448    1.3615    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    2.0113    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -2.1885   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -4.3532    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -1.5861   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -1.0214   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -2.7809   -0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    4.2401   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    2.8516   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18  3  1  0
  8  4  1  0
 18 12  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  END

Isopimpinellin
  Mrv1572001071617262D          

 18 20  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034312

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

> <INCHI_KEY>
DFMAXQKDIGCMTL-UHFFFAOYSA-N

> <FORMULA>
C13H10O5

> <MOLECULAR_WEIGHT>
246.218

> <EXACT_MASS>
246.052823422

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.837912622779488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.6271404846666666

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.864664323949568

> <JCHEM_POLAR_SURFACE_AREA>
57.900000000000006

> <JCHEM_REFRACTIVITY>
63.31610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopimpinellin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034312
     RDKit          3D
Isopimpinellin
 28 30  0  0  0  0  0  0  0  0999 V2000
    3.3520    1.1162    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.7271   -0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2284    0.1997   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -1.1507   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268   -2.2192   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -3.3483    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.9872    0.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.6806    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2954   -0.8480    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710   -1.3476    0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185   -1.7153   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1198    0.5108    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    1.3240    0.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639    2.6237    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581    3.3926    0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8276    3.1702   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    2.3837   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    1.0295   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    0.2848    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3448    1.3615    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    2.0113    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -2.1885   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -4.3532    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -1.5861   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -1.0214   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -2.7809   -0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    4.2401   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    2.8516   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18  3  1  0
  8  4  1  0
 18 12  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isopimpinellin                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.704   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   18                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0034312
HETATM    1  C1  UNL     1       3.352   1.116   0.677  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.492   0.727  -0.368  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.228   0.200  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.041  -1.151  -0.008  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.927  -2.219  -0.042  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.170  -3.348   0.159  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.103  -2.987   0.306  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.206  -1.681   0.210  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.295  -0.848   0.292  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.571  -1.348   0.512  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.419  -1.715  -0.585  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.120   0.511   0.153  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.146   1.324   0.228  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.064   2.624   0.107  1.00  0.00           C  
HETATM   15  O5  UNL     1      -3.058   3.393   0.181  1.00  0.00           O  
HETATM   16  C11 UNL     1      -0.828   3.170  -0.111  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.317   2.384  -0.204  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.147   1.030  -0.067  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.512   0.285   1.397  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.345   1.361   0.230  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.997   2.011   1.221  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.985  -2.189  -0.192  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.573  -4.353   0.187  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.863  -1.586  -1.560  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.292  -1.021  -0.528  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.728  -2.781  -0.456  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.678   4.240  -0.221  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.284   2.852  -0.378  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5    8
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   12
CONECT   10   11
CONECT   11   24   25   26
CONECT   12   13   18   18
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17   27
CONECT   17   18   28
END

HMDB0034312
     RDKit          3D
Isopimpinellin
 28 30  0  0  0  0  0  0  0  0999 V2000
    3.3520    1.1162    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.7271   -0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2284    0.1997   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -1.1507   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268   -2.2192   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -3.3483    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.9872    0.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.6806    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2954   -0.8480    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710   -1.3476    0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185   -1.7153   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1198    0.5108    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    1.3240    0.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639    2.6237    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581    3.3926    0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8276    3.1702   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    2.3837   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    1.0295   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    0.2848    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3448    1.3615    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    2.0113    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -2.1885   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729   -4.3532    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -1.5861   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -1.0214   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -2.7809   -0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    4.2401   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    2.8516   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18  3  1  0
  8  4  1  0
 18 12  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,8-Dimethoxypsoralen	ChEBI
5,8-Dimethoxypsoralene	ChEBI
4,9-Dimethoxy-7-oxofuro[3,2-g]chromene	HMDB
4,9-Dimethoxy-7H-furo(3,2-g) (1)benzopyran-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9ci	HMDB
4,9-Dimethoxy-furo[3,2-g]chromen-7-one	HMDB
4,9-Dimethoxypsoralen	HMDB
5, 8-Dimethoxypsoralene	HMDB
5,8-Dimethoxy-6,7-furanocoumarin	HMDB
7H-furo(3,2-g)(1)Benzopyran-7-one, 4,9-dimethoxy- (8ci)	HMDB
Dimethylpsoralen	HMDB
Isopimpinellin (4,9-dimethoxypsoralen)	HMDB

Chemical Formula

C₁₃H₁₀O₅

Average Molecular Weight

246.218

Monoisotopic Molecular Weight

246.052823422

IUPAC Name

4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

isopimpinellin

CAS Registry Number

482-27-9

SMILES

COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

InChI Key

DFMAXQKDIGCMTL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
8-methoxypsoralen
1-benzopyran
Benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:28853 )
Furanocoumarins (C02162 )

Ontology

Physiological effect

Health effect

Edema (HMDB: HMDB0034312)

Skin and subcutaneous tissue disorder

Erythema (HMDB: HMDB0034312)

Disposition

Biological location

Extracellular (HMDB: HMDB0034312)

Cellular substructure

Extracellular (HMDB: HMDB0034312)
Cytoplasm (HMDB: HMDB0034312)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034312)

Source

Exogenous

Food

Food (HMDB: HMDB0034312)

Vegetable

Root vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)
Anise (FooDB: FOOD00137)
Angelica (FooDB: FOOD00001)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)

Endogenous

Plant

Plant (HMDB: HMDB0034312)

Not Available

Nutrient (HMDB: HMDB0034312)

Industrial application

Manufacturing industry

Material processing agent

insecticide (HMDB: HMDB0034312)
pesticide (HMDB: HMDB0034312)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151 °C	Not Available
Boiling Point	448.00 to 449.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	315.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.407 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	146.461	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001428

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.32 m³·mol⁻¹	ChemAxon
Polarizability	23.84 Å³	ChemAxon
Number of Rings	3	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]+	155.487	31661259
DarkChem	[M-H]-	156.135	31661259
DeepCCS	[M+H]+	152.905	30932474
DeepCCS	[M-H]-	150.547	30932474
DeepCCS	[M-2H]-	183.437	30932474
DeepCCS	[M+Na]+	158.999	30932474
AllCCS	[M+H]+	152.2	32859911
AllCCS	[M+H-H2O]+	148.1	32859911
AllCCS	[M+NH4]+	156.0	32859911
AllCCS	[M+Na]+	157.1	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	153.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopimpinellin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2	3200.6	Standard polar	33892256
Isopimpinellin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2	2107.0	Standard non polar	33892256
Isopimpinellin	COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2	2228.7	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 - Isopimpinellin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1190000000-275fee6a0dc6bf75820a	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopimpinellin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopimpinellin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000t-7690000000-e6fa32711c30bc186816	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-001i-0090000000-a0c532fce25db07d90ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-001i-0090000000-54e2a9d485cc8bdceb6d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-001i-0090000000-1032f4d166b576b7ff20	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-001i-0090000000-9c87bfda7e5ffe9c5af4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-ea38f4e14acc089f6b51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-a3f55b3b5507de3ae999	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin , positive-QTOF	splash10-014i-0970000000-1e191da648efe9b73b12	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin , positive-QTOF	splash10-014i-0290000000-bdc222e3350bd6ef6486	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin , positive-QTOF	splash10-014j-0190000000-908c9053908baf8cf954	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOF	splash10-07vr-0920000000-5af7d91dde7af1b89547	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOF	splash10-014i-0190000000-dfa5b17d7b2df4661d05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOF	splash10-0002-0090000000-278fc8d7828591790af9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOF	splash10-0002-0090000000-49418fa141b50d6f7f71	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOF	splash10-0002-0090000000-730804c160e7a2b01bf9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOF	splash10-014i-0390000000-ee25336a941ea1bf779b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 10V, Negative-QTOF	splash10-0002-0090000000-bbb8af93a94542f5b653	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 20V, Negative-QTOF	splash10-0002-0090000000-cef1eff8d1ded6b77f3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 40V, Negative-QTOF	splash10-0fki-0960000000-d96e6099792968341c94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 10V, Negative-QTOF	splash10-0002-0090000000-f541a876b9ec3249e209	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 20V, Negative-QTOF	splash10-0002-0090000000-05d9c28202aea63dacbe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 40V, Negative-QTOF	splash10-000i-0920000000-1148e3f152ca14bca10d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOF	splash10-0002-0090000000-14343c13950e873267f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOF	splash10-0002-0090000000-14343c13950e873267f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOF	splash10-0002-0090000000-aa4ade1addb5f0cbc93a	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isopimpinellin

METLIN ID

Not Available

PubChem Compound

68079

PDB ID

Not Available

ChEBI ID

28853

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1102171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isopimpinellin (HMDB0034312)

MOL for HMDB0034312 (Isopimpinellin)

3D MOL for HMDB0034312 (Isopimpinellin)

3D SDF for HMDB0034312 (Isopimpinellin)

3D-SDF for HMDB0034312 (Isopimpinellin)

PDB for HMDB0034312 (Isopimpinellin)

3D PDB for HMDB0034312 (Isopimpinellin)

SMILES for HMDB0034312 (Isopimpinellin)

INCHI for HMDB0034312 (Isopimpinellin)

Structure for HMDB0034312 (Isopimpinellin)

3D Structure for HMDB0034312 (Isopimpinellin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra