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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:01:58 UTC

Update Date

2021-09-23 03:01:58 UTC

HMDB ID

HMDB0301849

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Peucedanin

Description

Peucedanin, also known as 2-isopropyl-3-methoxy-7h-furo[3,2-g]chromen-7-one or 4-methoxy-5-isopropylfuro(2,3:6,7)coumarin, is a member of the class of compounds known as psoralens. Psoralens 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. Peucedanin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Peucedanin can be found in carrot, chervil, and wild carrot, which makes peucedanin a potential biomarker for the consumption of these food products.

Structure

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

HMDB0301849
     RDKit          3D
Peucedanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8342    2.8687    1.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    1.7818    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.7044    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -0.3546   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.3131   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067   -0.0669   -1.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8634   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -1.2849   -0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4348   -0.9496   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.6054   -0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -1.0721   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832   -1.6943   -0.3608 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -1.1664   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1799   -1.8672   -0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2429    0.0516    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562    0.7675    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056    0.1731    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6923    0.8232    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941    0.2795    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1734    3.7698    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    2.7003    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.2598    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705    0.1983    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934    0.0212   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.8990   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034   -0.8783   -2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939   -1.9921   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.1848    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407   -2.4127   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -2.6001   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1699    0.4960    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.7326    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417    1.7790    1.1912 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  1  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19  9  1  0
 17 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv0541 02241221262D          

 19 21  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   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
    1.4289    0.0000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   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
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -2.8902    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
    2.8579   -1.6500    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
    1.4289   -1.6500    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
    5.6669   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301849

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC2=CC3=C(C=CC(=O)O3)C=C12)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3

> <INCHI_KEY>
YQBNJPACAUPNLV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.5537132756696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-2-(propan-2-yl)-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.8718682946666663

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2570871709816775

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
70.99820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
peucedanin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301849
     RDKit          3D
Peucedanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8342    2.8687    1.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    1.7818    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.7044    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -0.3546   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.3131   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067   -0.0669   -1.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8634   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -1.2849   -0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4348   -0.9496   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.6054   -0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -1.0721   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832   -1.6943   -0.3608 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -1.1664   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1799   -1.8672   -0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2429    0.0516    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562    0.7675    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056    0.1731    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6923    0.8232    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941    0.2795    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1734    3.7698    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    2.7003    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.2598    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705    0.1983    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934    0.0212   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.8990   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034   -0.8783   -2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939   -1.9921   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.1848    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407   -2.4127   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -2.6001   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1699    0.4960    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.7326    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417    1.7790    1.1912 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  1  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19  9  1  0
 17 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.578  -5.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.578  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.348  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.348  -0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0301849
HETATM    1  C1  UNL     1      -1.834   2.869   1.459  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.342   1.782   0.950  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.856   0.704   0.454  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.581  -0.355  -0.139  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.030  -0.313  -0.205  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.607  -0.067  -1.609  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.443  -1.863  -0.023  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.790  -1.285  -0.549  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.435  -0.950  -0.278  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.650  -1.605  -0.507  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.851  -1.072  -0.145  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.983  -1.694  -0.361  1.00  0.00           O  
HETATM   13  C10 UNL     1       5.143  -1.166  -0.012  1.00  0.00           C  
HETATM   14  O4  UNL     1       6.180  -1.867  -0.290  1.00  0.00           O  
HETATM   15  C11 UNL     1       5.243   0.052   0.596  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.056   0.767   0.864  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.906   0.173   0.480  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.692   0.823   0.711  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.494   0.280   0.347  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.173   3.770   1.525  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.411   2.700   2.404  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.672   3.260   0.775  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.570   0.198   0.576  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.693   0.021  -1.490  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.252   0.899  -2.021  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.403  -0.878  -2.325  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.494  -1.992  -0.271  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.186  -2.185   0.971  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.841  -2.413  -0.819  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.604  -2.600  -0.978  1.00  0.00           H  
HETATM   31  H12 UNL     1       6.170   0.496   0.879  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.130   1.733   1.333  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.642   1.779   1.191  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    8
CONECT    5    6    7   23
CONECT    6   24   25   26
CONECT    7   27   28   29
CONECT    8    9
CONECT    9   10   10   19
CONECT   10   11   30
CONECT   11   12   17   17
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16   31
CONECT   16   17   32
CONECT   17   18
CONECT   18   19   19   33
END

HMDB0301849
     RDKit          3D
Peucedanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8342    2.8687    1.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    1.7818    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.7044    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -0.3546   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.3131   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067   -0.0669   -1.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4425   -1.8634   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -1.2849   -0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4348   -0.9496   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.6054   -0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -1.0721   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832   -1.6943   -0.3608 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -1.1664   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1799   -1.8672   -0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2429    0.0516    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562    0.7675    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056    0.1731    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6923    0.8232    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941    0.2795    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1734    3.7698    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    2.7003    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.2598    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705    0.1983    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934    0.0212   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.8990   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034   -0.8783   -2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939   -1.9921   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.1848    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407   -2.4127   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -2.6001   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1699    0.4960    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.7326    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417    1.7790    1.1912 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  1  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19  9  1  0
 17 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Isopropyl-3-methoxy-7H-furo[3,2-g]chromen-7-one	ChEBI
3-Methoxy-2-(1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one	ChEBI
4-Methoxy-5-isopropylfuro(2,3:6,7)coumarin	ChEBI
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid delta-lactone	ChEBI
Oreoselone methyl ether	ChEBI
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylate delta-lactone	Generator
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylate δ-lactone	Generator
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid δ-lactone	Generator

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

3-methoxy-2-(propan-2-yl)-7H-furo[3,2-g]chromen-7-one

Traditional Name

peucedanin

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC3=C(C=CC(=O)O3)C=C12)C(C)C

InChI Identifier

InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3

InChI Key

YQBNJPACAUPNLV-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

aromatic ether (CHEBI:8034 )
lactone (CHEBI:8034 )
furanocoumarin (CHEBI:8034 )
Furanocoumarins (C09283 )

Ontology

Not Available

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

Herb and spice

Spice

Chervil (FooDB: FOOD00327)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.41	ALOGPS
logP	2.87	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.3	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	2	ChemAxon
Refractivity	71 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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
AllCCS	[M+H]+	156.924	32859911
AllCCS	[M+H-H2O]+	152.988	32859911
AllCCS	[M+Na]+	161.637	32859911
AllCCS	[M+NH4]+	160.584	32859911
AllCCS	[M-H]-	162.995	32859911
AllCCS	[M+Na-2H]-	162.459	32859911
AllCCS	[M+HCOO]-	161.994	32859911
DeepCCS	[M-2H]-	192.515	30932474
DeepCCS	[M+Na]+	167.856	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 10V, Positive-QTOF	splash10-0a4i-0090000000-840f9375378175876525	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 20V, Positive-QTOF	splash10-0a4i-1090000000-1610572ae983994cfd56	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 40V, Positive-QTOF	splash10-00kg-2590000000-76a33abba9da863c58b3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 10V, Negative-QTOF	splash10-0a4i-0090000000-1425ce6d2826de62fe94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 20V, Negative-QTOF	splash10-0a4i-0090000000-04e86ab6aade04b343b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 40V, Negative-QTOF	splash10-01ow-1980000000-1b80f19aa04ee24e5cb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 10V, Positive-QTOF	splash10-0a4i-0090000000-5899da0eda98839d58ad	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 20V, Positive-QTOF	splash10-0a4i-0090000000-2fc269f07cae4269b7ba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 40V, Positive-QTOF	splash10-02ta-1930000000-9823a6bf623df44eebac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 10V, Negative-QTOF	splash10-0a4i-0090000000-c2a50a42dfada53572a9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 20V, Negative-QTOF	splash10-0a6r-0090000000-137f72438991a2f4a37a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peucedanin 40V, Negative-QTOF	splash10-0670-2930000000-ecf1d6028eb043a1dbf5	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8034

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1567831

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Peucedanin (HMDB0301849)

MOL for HMDB0301849 (Peucedanin)

3D MOL for HMDB0301849 (Peucedanin)

3D SDF for HMDB0301849 (Peucedanin)

3D-SDF for HMDB0301849 (Peucedanin)

PDB for HMDB0301849 (Peucedanin)

3D PDB for HMDB0301849 (Peucedanin)

SMILES for HMDB0301849 (Peucedanin)

INCHI for HMDB0301849 (Peucedanin)

Structure for HMDB0301849 (Peucedanin)

3D Structure for HMDB0301849 (Peucedanin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra