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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:12:04 UTC

Update Date

2022-03-07 02:54:04 UTC

HMDB ID

HMDB0034376

Secondary Accession Numbers

HMDB34376

Metabolite Identification

Common Name

Imperatorin

Description

Imperatorin, also known as ammidin or marmelosin, 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. Imperatorin is found, on average, in the highest concentration within a few different foods, such as parsnips (Pastinaca sativa), lovages (Levisticum officinale), and parsleys (Petroselinum crispum) and in a lower concentration in fennels (Foeniculum vulgare). Imperatorin has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), root vegetables, anises (Pimpinella anisum), lambsquarters (Chenopodium album), and wild celeries (Apium graveolens). This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin 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 Imperatorin.

Structure

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

HMDB0034376
     RDKit          3D
Imperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.7711    1.0400    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -0.4070    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -1.0797   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447   -1.1031    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067   -0.4115    0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.5606   -0.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.1153   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795    1.1371   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    2.0140   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    3.0779   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    2.9123   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.6718   -0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.9588   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.2828    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -0.9863    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332   -2.2350    1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -2.7062    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -3.8408    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -1.9556    0.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.7854    0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165    1.6210   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.4563    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.2756    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -1.8272   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.3670   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767   -1.6569    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -2.1856    0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -0.7779    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6404    0.6649    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4138    3.9189   -2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    3.6111   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.4075   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3210   -0.6218    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.8616    1.5378 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  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
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv0541 09051417012D          

 20 22  0  0  0  0            999 V2000
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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 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
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    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
    2.8579   -4.1250    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
    3.5724   -0.4125    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
    3.5724   -1.2375    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  4  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 13  2  0  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 19  7  1  0  0  0  0
 19 16  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034376

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2

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

> <INCHI_KEY>
OLOOJGVNMBJLLR-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.325859943816432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.14605784

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9261466917215975

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
75.97109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
imperatorin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034376
     RDKit          3D
Imperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.7711    1.0400    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -0.4070    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -1.0797   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447   -1.1031    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067   -0.4115    0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.5606   -0.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.1153   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795    1.1371   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    2.0140   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    3.0779   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    2.9123   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.6718   -0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.9588   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.2828    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -0.9863    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332   -2.2350    1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -2.7062    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -3.8408    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -1.9556    0.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.7854    0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165    1.6210   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.4563    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.2756    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -1.8272   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.3670   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767   -1.6569    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -2.1856    0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -0.7779    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6404    0.6649    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4138    3.9189   -2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    3.6111   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.4075   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3210   -0.6218    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.8616    1.5378 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  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
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    7   10                                                       
CONECT    6    8   12                                                       
CONECT    7    5   19                                                       
CONECT    8    6   18                                                       
CONECT    9   11   12                                                       
CONECT   10    1    2    5                                                  
CONECT   11    3    9   15                                                  
CONECT   12    6    9   14                                                  
CONECT   13    4   17   20                                                  
CONECT   14   12   16   18                                                  
CONECT   15   11   16   20                                                  
CONECT   16   14   15   19                                                  
CONECT   17   13                                                            
CONECT   18    8   14                                                       
CONECT   19    7   16                                                       
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0034376
HETATM    1  C1  UNL     1       3.771   1.040   0.416  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.749  -0.407   0.137  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.982  -1.080  -0.314  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.645  -1.103   0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.407  -0.412   0.741  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.437  -0.561  -0.227  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.845  -0.115  -0.274  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.079   1.137  -0.838  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.270   2.014  -1.358  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.912   3.078  -1.780  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.272   2.912  -1.528  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.355   1.672  -0.928  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.432   0.959  -0.452  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.228  -0.283   0.111  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.317  -0.986   0.584  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.033  -2.235   1.140  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.735  -2.706   1.197  1.00  0.00           C  
HETATM   18  O3  UNL     1      -2.508  -3.841   1.706  1.00  0.00           O  
HETATM   19  O4  UNL     1      -1.786  -1.956   0.720  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.949  -0.785   0.185  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.116   1.621  -0.264  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.800   1.456   0.297  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.485   1.276   1.471  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.819  -1.827  -1.108  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.753  -0.367  -0.695  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.377  -1.657   0.569  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.638  -2.186   0.074  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.140  -0.778   1.747  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.640   0.665   0.849  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.414   3.919  -2.243  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.065   3.611  -1.758  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.418   1.408  -0.539  1.00  0.00           H  
HETATM   33  H13 UNL     1      -5.321  -0.622   0.540  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.819  -2.862   1.538  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
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13
CONECT   13   14   32
CONECT   14   15   20   20
CONECT   15   16   16   33
CONECT   16   17   34
CONECT   17   18   18   19
CONECT   19   20
END

HMDB0034376
     RDKit          3D
Imperatorin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.7711    1.0400    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -0.4070    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -1.0797   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447   -1.1031    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067   -0.4115    0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.5606   -0.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.1153   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795    1.1371   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    2.0140   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    3.0779   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    2.9123   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.6718   -0.9285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.9588   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.2828    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -0.9863    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332   -2.2350    1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -2.7062    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084   -3.8408    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -1.9556    0.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.7854    0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165    1.6210   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.4563    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.2756    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -1.8272   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.3670   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767   -1.6569    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -2.1856    0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -0.7779    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6404    0.6649    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4138    3.9189   -2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    3.6111   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.4075   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3210   -0.6218    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.8616    1.5378 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  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
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Isoamylenoxypsoralen	ChEBI
8-Isopentenyloxypsoralene	ChEBI
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-one	ChEBI
Ammidin	ChEBI
Marmelosin	ChEBI
Pentosalen	ChEBI
5-Hydroxy-8-(1,1-dimethylallyl)psoralen	HMDB
9-(3-Methyl-2-butenyloxy)-7-oxofuro[3,2-g]chromene	HMDB
9-(3-Methylbut-2-enyloxy)-7H-furo(3,2-g)chromen-7-one	HMDB
9-(3-Methylbut-2-enyloxy)furo[3,2-g]chromen-7-one	HMDB
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ci	HMDB
9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one	HMDB
Marmelide	HMDB
Pentasalen, ban	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

Traditional Name

imperatorin

CAS Registry Number

482-44-0

SMILES

CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2

InChI Identifier

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

InChI Key

OLOOJGVNMBJLLR-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:5885 )
Furanocoumarins (C09269 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0034376)
Hypotension (HMDB: HMDB0034376)

Nervous system disorder

Headache (HMDB: HMDB0034376)
Tremor (HMDB: HMDB0034376)

Central nervous system disorder

Psychiatric disorder

Depression (HMDB: HMDB0034376)
Anxiety (HMDB: HMDB0034376)

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0034376)
Nausea (HMDB: HMDB0034376)

Skin and subcutaneous tissue disorder

Erythema (HMDB: HMDB0034376)

Disposition

Biological location

Cell membrane (HMDB: HMDB0034376)

Cellular substructure

Membrane (HMDB: HMDB0034376)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034376)

Source

Exogenous

Food

Food (HMDB: HMDB0034376)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Dill (FooDB: FOOD00013)
Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)
Anise (FooDB: FOOD00137)
Lovage (FooDB: FOOD00100)

Fruit

Citrus

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

Fruits (FooDB: FOOD00871)

Vegetable

Root vegetable

Parsnip (FooDB: FOOD00129)
Root vegetables (FooDB: FOOD00873)

Leaf vegetable

Lambsquarters (FooDB: FOOD00394)

Endogenous

Plant

Plant (HMDB: HMDB0034376)

Not Available

acetylcholinesterase inhibitor (HMDB: HMDB0034376)
cytochrome-P450 inhibitor (HMDB: HMDB0034376)
diabetic-macular-edema inhibitor (HMDB: HMDB0034376)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0034376)

Nutrient

Nutrient (HMDB: HMDB0034376)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

molluscicide (HMDB: HMDB0034376)
sedative (HMDB: HMDB0034376)

Pharmaceutical industry

Anticonvulsant (HMDB: HMDB0034376)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 °C	Not Available
Boiling Point	448.00 to 449.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	635.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.983 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.15	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.9	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	28.33 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]+	164.084	31661259
DarkChem	[M-H]-	162.304	31661259
DeepCCS	[M+H]+	160.289	30932474
DeepCCS	[M-H]-	157.931	30932474
DeepCCS	[M-2H]-	190.816	30932474
DeepCCS	[M+Na]+	166.382	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imperatorin	CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2	3266.4	Standard polar	33892256
Imperatorin	CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2	2327.3	Standard non polar	33892256
Imperatorin	CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2	2358.1	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 - Imperatorin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0q4l-5490000000-8addd2b7e7d5a89c1657	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imperatorin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-3290000000-ccce724ec532a9b1c7ae	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 - Imperatorin 40V, Positive-QTOF	splash10-0002-2900000000-a48f50b827aed0c2c74e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOF	splash10-0udi-1390000000-a4331e3b6e6ab9ba18c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOF	splash10-0udi-1090000000-25f99a63f2c9348d2805	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOF	splash10-00di-1090000000-205792cde142f77aa94f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOF	splash10-014i-9080000000-7795cfce5b3fcd729d41	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 40V, Positive-QTOF	splash10-0uxu-9540000000-7130c7ebffd168204435	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 10V, Negative-QTOF	splash10-014i-0090000000-6f0805a46d8f54b963d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 20V, Negative-QTOF	splash10-0udi-0290000000-cdea20e125d3564dc0ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 40V, Negative-QTOF	splash10-0a4i-1920000000-a1c90224178c9971284d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOF	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOF	splash10-0udi-0190000000-58ef289697c902aee31e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 40V, Positive-QTOF	splash10-004i-2950000000-6ffc6c72bc8380498c4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 10V, Negative-QTOF	splash10-0gb9-0090000000-e4734d549fe36cc62202	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 20V, Negative-QTOF	splash10-0udi-0090000000-3a57f1382615518fb5d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imperatorin 40V, Negative-QTOF	splash10-0uk9-0790000000-eef12a3af90025252e5c	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imperatorin

METLIN ID

Not Available

PubChem Compound

10212

PDB ID

Not Available

ChEBI ID

5885

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027431

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Luszczki JJ, Andres-Mach M, Glensk M, Skalicka-Wozniak K: Anticonvulsant effects of four linear furanocoumarins, bergapten, imperatorin, oxypeucedanin, and xanthotoxin, in the mouse maximal electroshock-induced seizure model: a comparative study. Pharmacol Rep. 2010 Nov-Dec;62(6):1231-6. [PubMed:21273683 ]
Zhang Y, Cao Y, Zhan Y, Duan H, He L: Furanocoumarins-imperatorin inhibits myocardial hypertrophy both in vitro and in vivo. Fitoterapia. 2010 Dec;81(8):1188-95. doi: 10.1016/j.fitote.2010.07.023. Epub 2010 Aug 4. [PubMed:20691250 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Imperatorin (HMDB0034376)

MOL for HMDB0034376 (Imperatorin)

3D MOL for HMDB0034376 (Imperatorin)

3D SDF for HMDB0034376 (Imperatorin)

3D-SDF for HMDB0034376 (Imperatorin)

PDB for HMDB0034376 (Imperatorin)

3D PDB for HMDB0034376 (Imperatorin)

SMILES for HMDB0034376 (Imperatorin)

INCHI for HMDB0034376 (Imperatorin)

Structure for HMDB0034376 (Imperatorin)

3D Structure for HMDB0034376 (Imperatorin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra