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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:47:06 UTC

Update Date

2021-09-26 23:12:00 UTC

HMDB ID

HMDB0256386

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phellopterin

Description

Phellopterin belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Phellopterin has been detected, but not quantified in, a few different foods, such as lemons (Citrus limon), limes (Citrus aurantiifolia), and wild celeries (Apium graveolens). This could make phellopterin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phellopterin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phellopterin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phellopterin 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

HMDB0256386
     RDKit          3D
Phellopterin
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.1809   -0.9520    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0962   -0.4250    1.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886   -0.4819    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.5904    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751   -2.7294    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -3.4801    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -2.8137    1.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -1.6907    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121   -0.6488   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.7238   -0.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934   -0.2222    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -0.4515   -0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    0.5238   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606    1.9279   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5044    0.2876   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    0.4525   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.4373   -1.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    2.4961   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    3.4167   -2.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    2.6756   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    1.6502   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724    0.5437   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517   -1.2923   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.1479    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328   -1.8252    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -3.0146    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -4.4546    2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002    0.8529    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -0.7065    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -1.4695   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    2.2480   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472    1.9848    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749    2.6448   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -0.5848   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3891    0.1523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645    1.1689   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    3.5434   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0328    1.6986   -0.0571 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22  3  1  0
  8  4  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 20 37  1  0
 21 38  1  0
M  END

  Mrv0541 02241204592D          

 22 24  0  0  0  0            999 V2000
    1.4289    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
    2.1434   -1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
  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
  4  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  9 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 22  2  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256386

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3

> <INCHI_KEY>
BMLZFLQMBMYVHG-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.247790218114417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.988386574333333

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.069325039518298

> <JCHEM_POLAR_SURFACE_AREA>
57.9

> <JCHEM_REFRACTIVITY>
82.4343

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256386
     RDKit          3D
Phellopterin
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.1809   -0.9520    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0962   -0.4250    1.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886   -0.4819    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.5904    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751   -2.7294    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -3.4801    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -2.8137    1.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -1.6907    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121   -0.6488   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.7238   -0.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934   -0.2222    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -0.4515   -0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    0.5238   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606    1.9279   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5044    0.2876   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    0.4525   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.4373   -1.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    2.4961   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    3.4167   -2.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    2.6756   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    1.6502   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724    0.5437   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517   -1.2923   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.1479    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328   -1.8252    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -3.0146    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -4.4546    2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002    0.8529    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -0.7065    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -1.4695   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    2.2480   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472    1.9848    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749    2.6448   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -0.5848   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3891    0.1523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645    1.1689   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    3.5434   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0328    1.6986   -0.0571 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22  3  1  0
  8  4  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 20 37  1  0
 21 38  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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.704   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   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   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
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   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0256386
HETATM    1  C1  UNL     1       5.181  -0.952   0.419  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.096  -0.425   1.162  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.789  -0.482   0.708  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.030  -1.590   1.051  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.275  -2.729   1.783  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.121  -3.480   1.777  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.239  -2.814   1.073  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.713  -1.691   0.617  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.212  -0.649  -0.155  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.079  -0.724  -0.593  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.193  -0.222   0.120  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.456  -0.451  -0.608  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.249   0.524  -0.991  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.861   1.928  -0.679  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.504   0.288  -1.716  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.967   0.452  -0.495  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.472   1.437  -1.233  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.168   2.496  -1.571  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.648   3.417  -2.282  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.483   2.676  -1.183  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.017   1.650  -0.407  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.272   0.544  -0.061  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.852  -1.292  -0.602  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.944  -0.148   0.360  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.633  -1.825   0.943  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.186  -3.015   2.282  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.953  -4.455   2.263  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.000   0.853   0.314  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.296  -0.706   1.122  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.743  -1.470  -0.837  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.946   2.248  -1.214  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.747   1.985   0.428  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.675   2.645  -0.943  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.438  -0.585  -2.424  1.00  0.00           H  
HETATM   35  H13 UNL     1      -6.389   0.152  -1.042  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.764   1.169  -2.365  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.058   3.543  -1.458  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.033   1.699  -0.057  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5    8
CONECT    5    6    6   26
CONECT    6    7   27
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   16
CONECT   10   11
CONECT   11   12   28   29
CONECT   12   13   13   30
CONECT   13   14   15
CONECT   14   31   32   33
CONECT   15   34   35   36
CONECT   16   17   22   22
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   21   37
CONECT   21   22   38
END

HMDB0256386
     RDKit          3D
Phellopterin
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.1809   -0.9520    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0962   -0.4250    1.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886   -0.4819    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.5904    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751   -2.7294    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -3.4801    1.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -2.8137    1.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -1.6907    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121   -0.6488   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.7238   -0.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934   -0.2222    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -0.4515   -0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    0.5238   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606    1.9279   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5044    0.2876   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    0.4525   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.4373   -1.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    2.4961   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    3.4167   -2.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    2.6756   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    1.6502   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724    0.5437   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517   -1.2923   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.1479    0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328   -1.8252    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -3.0146    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -4.4546    2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002    0.8529    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -0.7065    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -1.4695   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    2.2480   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472    1.9848    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749    2.6448   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -0.5848   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3891    0.1523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645    1.1689   -2.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    3.5434   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0328    1.6986   -0.0571 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
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22  3  1  0
  8  4  1  0
 22 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2

InChI Identifier

InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3

InChI Key

BMLZFLQMBMYVHG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-methoxypsoralens

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:80887 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0256386)

Source

Exogenous

Exogenous (HMDB: HMDB0256386)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Fruit

Citrus

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

Process

Not Available

Role

Biological role

Calcium antagonist (HMDB: HMDB0256386)
Lipolytic (HMDB: HMDB0256386)

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	3.56	ALOGPS
logP	2.99	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-3.1	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	4	ChemAxon
Refractivity	82.43 m³·mol⁻¹	ChemAxon
Polarizability	31.25 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]+	168.401	30932474
DeepCCS	[M-H]-	166.043	30932474
DeepCCS	[M-2H]-	199.606	30932474
DeepCCS	[M+Na]+	174.833	30932474
AllCCS	[M+H]+	167.5	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.7	32859911
AllCCS	[M-H]-	173.5	32859911
AllCCS	[M+Na-2H]-	172.8	32859911
AllCCS	[M+HCOO]-	172.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phellopterin	COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2	3393.7	Standard polar	33892256
Phellopterin	COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2	2462.1	Standard non polar	33892256
Phellopterin	COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2	2562.9	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 - Phellopterin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-1290000000-afef60075ef55803aa37	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phellopterin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0159-5290000000-c6bda842d6e5e427846f	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 - Phellopterin 10V, Positive-QTOF	splash10-001i-0090000000-27b231c92641c9254a17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phellopterin 20V, Positive-QTOF	splash10-00lr-1090000000-3ff8129a0f3ae797307c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phellopterin 40V, Positive-QTOF	splash10-014i-1970000000-7c033cb0f0280e448efd	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 10V, Positive-QTOF	splash10-0udi-2039000000-32ef5805aca12f3a0de3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 20V, Positive-QTOF	splash10-014i-9062000000-8dd30f1ac063a129d47b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 40V, Positive-QTOF	splash10-014i-9170000000-3d240acaa8ebfceeaf9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 10V, Negative-QTOF	splash10-0002-0090000000-bb9f27aad8efd0e1848b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 20V, Negative-QTOF	splash10-01q9-0190000000-9dedf08f25531f236d52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phellopterin 40V, Negative-QTOF	splash10-01p9-1590000000-e8fab0a80e5aa7bb1e8f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

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

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1053021

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 Phellopterin (HMDB0256386)

MOL for HMDB0256386 (Phellopterin)

3D MOL for HMDB0256386 (Phellopterin)

3D SDF for HMDB0256386 (Phellopterin)

3D-SDF for HMDB0256386 (Phellopterin)

PDB for HMDB0256386 (Phellopterin)

3D PDB for HMDB0256386 (Phellopterin)

SMILES for HMDB0256386 (Phellopterin)

INCHI for HMDB0256386 (Phellopterin)

Structure for HMDB0256386 (Phellopterin)

3D Structure for HMDB0256386 (Phellopterin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra