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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:26:50 UTC

Update Date

2022-09-22 17:44:24 UTC

HMDB ID

HMDB0253646

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isoimperatorin

Description

Isoimperatorin belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Isoimperatorin is found, on average, in the highest concentration within parsleys (Petroselinum crispum). Isoimperatorin has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), limes (Citrus aurantiifolia), parsnips (Pastinaca sativa), and wild celeries (Apium graveolens). This could make isoimperatorin a potential biomarker for the consumption of these foods. Isoimperatorin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Isoimperatorin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isoimperatorin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isoimperatorin 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

HMDB0253646
     RDKit          3D
Isoimperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2866   -1.1661   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701   -0.4426    0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -0.7079    1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4324    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.6966    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1266    0.3706    0.8106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374    0.4925    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8612    1.6624    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5684    2.8644    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720    3.6693    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    2.9981    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    1.8004   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    0.7480   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.4315   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.4338   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -2.5606   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -3.5058   -2.3901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -2.7695   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.7294   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291   -0.5470   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246   -1.8469   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -1.6961   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702   -0.4347   -1.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9379   -1.7026    1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.7975    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    0.0975    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618    0.9898    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4051    0.1238   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.7747   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    3.1462    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    4.6848    1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    0.8345   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -3.7219   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530   -1.8919   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 12  8  1  0
 20 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv0541 02241204312D          

 20 22  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    2.1434    1.2375    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
    3.6425    1.0799    0.0000 C   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   -0.2549    0.0000 O   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
    2.1434   -0.4125    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
    1.4289    0.8250    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  7 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253646

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3

> <INCHI_KEY>
IGWDEVSBEKYORK-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.255766570828797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.14605784

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.825419758055636

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
75.9711

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(3-methylbut-2-en-1-yl)oxy]furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253646
     RDKit          3D
Isoimperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2866   -1.1661   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701   -0.4426    0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -0.7079    1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4324    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.6966    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1266    0.3706    0.8106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374    0.4925    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8612    1.6624    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5684    2.8644    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720    3.6693    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    2.9981    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    1.8004   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    0.7480   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.4315   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.4338   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -2.5606   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -3.5058   -2.3901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -2.7695   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.7294   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291   -0.5470   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246   -1.8469   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -1.6961   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702   -0.4347   -1.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9379   -1.7026    1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.7975    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    0.0975    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618    0.9898    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4051    0.1238   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.7747   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    3.1462    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    4.6848    1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    0.8345   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -3.7219   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530   -1.8919   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 12  8  1  0
 20 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  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       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   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       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.704   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   14                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0253646
HETATM    1  C1  UNL     1       3.287  -1.166  -0.587  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.370  -0.443   0.698  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.500  -0.708   1.611  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.449   0.432   1.031  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.313   0.697   0.109  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.127   0.371   0.811  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.137   0.492   0.260  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.861   1.662   0.375  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.568   2.864   0.982  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.672   3.669   0.774  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.578   2.998   0.084  1.00  0.00           O  
HETATM   12  C10 UNL     1      -3.127   1.800  -0.170  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.710   0.748  -0.856  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.007  -0.432  -0.984  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.547  -1.434  -1.631  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.891  -2.561  -1.760  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.443  -3.506  -2.390  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.628  -2.770  -1.244  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.039  -1.729  -0.560  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.729  -0.547  -0.425  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.125  -1.847  -0.759  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.297  -1.696  -0.602  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.270  -0.435  -1.445  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.938  -1.703   1.370  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.157  -0.798   2.681  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.262   0.098   1.610  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.462   0.990   1.959  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.405   0.124  -0.837  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.280   1.775  -0.183  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.671   3.146   1.516  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.739   4.685   1.138  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.705   0.834  -1.293  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.134  -3.722  -1.382  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.053  -1.892  -0.157  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7
CONECT    7    8    8   20
CONECT    8    9   12
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12
CONECT   12   13   13
CONECT   13   14   32
CONECT   14   15   20   20
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   19   33
CONECT   19   20   34
END

HMDB0253646
     RDKit          3D
Isoimperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2866   -1.1661   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701   -0.4426    0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -0.7079    1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.4324    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.6966    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1266    0.3706    0.8106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374    0.4925    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8612    1.6624    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5684    2.8644    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720    3.6693    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    2.9981    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    1.8004   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    0.7480   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.4315   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.4338   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -2.5606   -1.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -3.5058   -2.3901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -2.7695   -1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.7294   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291   -0.5470   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246   -1.8469   -0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -1.6961   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702   -0.4347   -1.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9379   -1.7026    1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565   -0.7975    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623    0.0975    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618    0.9898    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4051    0.1238   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.7747   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    3.1462    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    4.6848    1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    0.8345   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343   -3.7219   -1.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530   -1.8919   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  7  1  0
 12  8  1  0
 20 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,4-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-one	ChEBI
iso-Imperatorin	MeSH

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

4-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

Traditional Name

4-[(3-methylbut-2-en-1-yl)oxy]furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2

InChI Identifier

InChI=1S/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3

InChI Key

IGWDEVSBEKYORK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:66071 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0253646)

Source

Exogenous

Exogenous (HMDB: HMDB0253646)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Parsley (FooDB: FOOD00131)

Fruit

Citrus

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

Vegetable

Root vegetable

Parsnip (FooDB: FOOD00129)

Process

Not Available

Role

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	3.67	ALOGPS
logP	3.15	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.97 m³·mol⁻¹	ChemAxon
Polarizability	28.26 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
DeepCCS	[M+H]+	158.131	30932474
DeepCCS	[M-H]-	155.773	30932474
DeepCCS	[M-2H]-	188.693	30932474
DeepCCS	[M+Na]+	164.224	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.8127 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2303.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	507.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	270.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	133.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	533.0 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	629.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1316.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	488.4 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	1344.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	372.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	453.9 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoimperatorin	CC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2	3188.9	Standard polar	33892256
Isoimperatorin	CC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2	2358.0	Standard non polar	33892256
Isoimperatorin	CC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2	2405.0	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 - Isoimperatorin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-5390000000-1bf0c24c340b994423c5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoimperatorin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0uxr-8290000000-27260c39496d6e0b6251	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 - Isoimperatorin 20V, Positive-QTOF	splash10-0udi-0290000000-6fc9699eb703287cc20c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoimperatorin 10V, Positive-QTOF	splash10-0udi-0090000000-91b67568346d3505ed84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoimperatorin 40V, Positive-QTOF	splash10-0005-5900000000-456019d3d6f24671b66c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoimperatorin 10V, Negative-QTOF	splash10-014i-0090000000-b0c02d050a925e7d5577	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoimperatorin 20V, Negative-QTOF	splash10-014i-3590000000-9f0a858c5257f0f68341	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoimperatorin 40V, Negative-QTOF	splash10-0wos-5960000000-45ec8597e6a51c9b31ac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 10V, Positive-QTOF	splash10-00di-1090000000-8ac6c0a5fb70291a1eaa	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 20V, Positive-QTOF	splash10-014i-9080000000-6df3f42b8b7e78aa7f2d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 40V, Positive-QTOF	splash10-0gb9-9530000000-fb7bbc5a1973fd1a795d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 10V, Negative-QTOF	splash10-014i-0090000000-300965788bf7c4527eb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 20V, Negative-QTOF	splash10-0udi-0290000000-9161a37ce9657cf9058e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 40V, Negative-QTOF	splash10-0a4i-0910000000-ff19b981b89111d7fcb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 10V, Positive-QTOF	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 20V, Positive-QTOF	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 40V, Positive-QTOF	splash10-0fb9-1940000000-e7dafddba6e1b2584175	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 10V, Negative-QTOF	splash10-014i-0090000000-d3eedc6d74870144d16f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 20V, Negative-QTOF	splash10-0udi-0190000000-55d1bfdb46af46eb4117	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoimperatorin 40V, Negative-QTOF	splash10-0pb9-2930000000-85deed983716c2656d62	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66071

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028021

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 Isoimperatorin (HMDB0253646)

MOL for HMDB0253646 (Isoimperatorin)

3D MOL for HMDB0253646 (Isoimperatorin)

3D SDF for HMDB0253646 (Isoimperatorin)

3D-SDF for HMDB0253646 (Isoimperatorin)

PDB for HMDB0253646 (Isoimperatorin)

3D PDB for HMDB0253646 (Isoimperatorin)

SMILES for HMDB0253646 (Isoimperatorin)

INCHI for HMDB0253646 (Isoimperatorin)

Structure for HMDB0253646 (Isoimperatorin)

3D Structure for HMDB0253646 (Isoimperatorin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra