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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:01 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030786

Secondary Accession Numbers

HMDB30786

Metabolite Identification

Common Name

Marmesin

Description

Nodakenetin 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. Nodakenetin has been detected, but not quantified in, wild celeries (Apium graveolens). This could make nodakenetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nodakenetin.

Structure

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

HMDB0030786
     RDKit          3D
Marmesin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8662    1.4445   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    0.2161   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223   -0.9719    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8828    0.0327   -1.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    0.2269    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585   -1.0144   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -0.5618   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -1.2416   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -0.5808   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462   -1.2961   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -0.6085   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1874    0.7698   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2716    1.4350   -0.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301    1.4091   -0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761    0.8076   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.4858   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.8161   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.2517   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    1.3508    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543    1.5448   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.3689   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -0.8038    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.0228    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075   -1.8632   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517    0.9382   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7265    0.2164    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426   -1.1919   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1466   -1.8868    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479   -2.3267   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -2.3770   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753   -1.1348   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6892    2.5678   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
M  END


  Mrv0541 02241215292D          

 18 20  0  0  0  0            999 V2000
   -3.2522   -0.7864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949    0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402    0.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    0.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6024   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046   -0.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265   -0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953   -0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019   -0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8237   -0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273   -0.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521    0.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2522   -0.0605    0.0000 O   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
  2 14  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030786

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3

> <INCHI_KEY>
FWYSBEAFFPBAQU-UHFFFAOYSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.2586

> <EXACT_MASS>
246.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.015733242109945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.7323936069999994

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.296805394683403

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1063773203654783

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
66.34090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
marmesin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030786
     RDKit          3D
Marmesin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8662    1.4445   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    0.2161   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223   -0.9719    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8828    0.0327   -1.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    0.2269    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585   -1.0144   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -0.5618   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -1.2416   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -0.5808   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462   -1.2961   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -0.6085   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1874    0.7698   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2716    1.4350   -0.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301    1.4091   -0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761    0.8076   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.4858   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.8161   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.2517   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    1.3508    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543    1.5448   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.3689   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -0.8038    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.0228    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075   -1.8632   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517    0.9382   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7265    0.2164    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426   -1.1919   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1466   -1.8868    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479   -2.3267   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -2.3770   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753   -1.1348   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6892    2.5678   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  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      -6.071  -1.468   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.726  -0.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.698   0.816   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.350   1.563   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.031   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.684   1.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.635   0.726   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.108   1.173   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.991  -0.085   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.062  -1.314   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.609  -0.816   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.738  -1.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.057  -0.767   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.404  -1.514   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.531  -0.113   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.324   1.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.278  -1.468   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.071  -0.113   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11    7   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13    5   12   14                                                  
CONECT   14    2   13                                                       
CONECT   15    9   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0030786
HETATM    1  C1  UNL     1      -3.866   1.444  -0.181  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.066   0.216  -0.477  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.822  -0.972   0.112  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.883   0.033  -1.846  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.706   0.227   0.171  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.959  -1.014  -0.330  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.452  -0.562  -0.288  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.653  -1.242  -0.261  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.871  -0.581  -0.223  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.046  -1.296  -0.197  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.237  -0.609  -0.159  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.187   0.770  -0.149  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.272   1.435  -0.114  1.00  0.00           O  
HETATM   14  O3  UNL     1       4.030   1.409  -0.175  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.876   0.808  -0.211  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.675   1.486  -0.238  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.448   0.816  -0.276  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.870   1.252  -0.309  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.404   1.351   0.806  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.654   1.545  -0.957  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.265   2.369  -0.099  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.913  -0.804   0.032  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.550  -1.023   1.185  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.508  -1.863  -0.449  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.752   0.938  -2.265  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.727   0.216   1.262  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.243  -1.192  -1.394  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.147  -1.887   0.307  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.648  -2.327  -0.270  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.073  -2.377  -0.205  1.00  0.00           H  
HETATM   31  H13 UNL     1       6.175  -1.135  -0.138  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.689   2.568  -0.228  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25
CONECT    5    6   18   26
CONECT    6    7   27   28
CONECT    7    8    8   17
CONECT    8    9   29
CONECT    9   10   15   15
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   32
CONECT   17   18
END

HMDB0030786
     RDKit          3D
Marmesin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8662    1.4445   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    0.2161   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223   -0.9719    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8828    0.0327   -1.8461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    0.2269    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585   -1.0144   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -0.5618   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -1.2416   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -0.5808   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462   -1.2961   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -0.6085   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1874    0.7698   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2716    1.4350   -0.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301    1.4091   -0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761    0.8076   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.4858   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.8161   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703    1.2517   -0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    1.3508    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543    1.5448   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    2.3689   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -0.8038    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.0228    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075   -1.8632   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517    0.9382   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7265    0.2164    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426   -1.1919   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1466   -1.8868    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479   -2.3267   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -2.3770   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753   -1.1348   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6892    2.5678   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  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
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  5  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Marmesin	HMDB
(S)-Marmesin	HMDB
S-(+)-Marmesin	HMDB

Chemical Formula

C₁₄H₁₄O₄

Average Molecular Weight

246.2586

Monoisotopic Molecular Weight

246.089208936

IUPAC Name

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

Traditional Name

marmesin

CAS Registry Number

13849-08-6

SMILES

CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1

InChI Identifier

InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3

InChI Key

FWYSBEAFFPBAQU-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
Coumaran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:49080 )
a coumarin (CPD-8191 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030786)
Cytoplasm (HMDB: HMDB0030786)

Source

Exogenous

Exogenous (HMDB: HMDB0030786)

Food

Herb and spice

Herb

Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)

Fruit

Other fruit

Fig (FooDB: FOOD00081)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189.5 °C	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
Water Solubility	0.37 g/L	ALOGPS
logP	1.98	ALOGPS
logP	1.73	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	26.02 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]+	157.738	31661259
DarkChem	[M-H]-	156.071	31661259
DeepCCS	[M+H]+	158.135	30932474
DeepCCS	[M-H]-	155.777	30932474
DeepCCS	[M-2H]-	188.663	30932474
DeepCCS	[M+Na]+	164.228	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.5 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0809 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.54 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marmesin	CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1	3129.6	Standard polar	33892256
Marmesin	CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1	2214.0	Standard non polar	33892256
Marmesin	CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1	2275.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Marmesin,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2437.9	Semi standard non polar	33892256
Marmesin,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2658.5	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 - Marmesin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9560000000-9c48be93f466828738ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marmesin GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9531000000-492bfcbfaad3c0574b12	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marmesin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marmesin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marmesin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marmesin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 10V, Positive-QTOF	splash10-002b-0090000000-1e79c1f020b61645f076	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 20V, Positive-QTOF	splash10-004j-0190000000-40afedd63981faa16804	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 40V, Positive-QTOF	splash10-01p9-3940000000-dbf2f2671711a438ee87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 10V, Negative-QTOF	splash10-0002-0090000000-d67ae6a47c04aa84c49b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 20V, Negative-QTOF	splash10-0002-0390000000-47033284f5fc203ed7ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 40V, Negative-QTOF	splash10-003i-1940000000-2854bff13b00322ef7e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 10V, Negative-QTOF	splash10-0002-0090000000-4a890656b917e493d11c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 20V, Negative-QTOF	splash10-0002-0390000000-fe362c9f11cb51306ecb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 40V, Negative-QTOF	splash10-001i-0940000000-12836f0c48948e3e7721	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 10V, Positive-QTOF	splash10-0002-0090000000-37e93f528798ad961b5e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 20V, Positive-QTOF	splash10-0002-0090000000-028034805bf719d92cf3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marmesin 40V, Positive-QTOF	splash10-0zgr-0930000000-c2454221b15eba87bc33	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012604

KNApSAcK ID

C00002485

Chemspider ID

525505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

604512

PDB ID

Not Available

ChEBI ID

49080

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Marmesin → 3,4,5-trihydroxy-6-[(2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propan-2-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Marmesin (HMDB0030786)

MOL for HMDB0030786 (Marmesin)

3D MOL for HMDB0030786 (Marmesin)

3D SDF for HMDB0030786 (Marmesin)

3D-SDF for HMDB0030786 (Marmesin)

PDB for HMDB0030786 (Marmesin)

3D PDB for HMDB0030786 (Marmesin)

SMILES for HMDB0030786 (Marmesin)

INCHI for HMDB0030786 (Marmesin)

Structure for HMDB0030786 (Marmesin)

3D Structure for HMDB0030786 (Marmesin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions