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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:32:42 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033783

Secondary Accession Numbers

HMDB33783

Metabolite Identification

Common Name

Marshrin

Description

Marshrin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Marshrin has been detected, but not quantified in, citrus. This could make marshrin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Marshrin.

Structure

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

HMDB0033783
     RDKit          3D
Marshrin
 35 38  0  0  0  0  0  0  0  0999 V2000
    0.7489    4.0846   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    2.7474   -0.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    1.6405   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4793    1.7676    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859    0.6142    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161   -0.6293    0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -1.7573    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -3.0018    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -3.0317    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9524   -4.1666   -0.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401   -1.9069   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -0.7191   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    0.3999   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102    0.3892   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.9565   -1.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.4258   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -2.5882   -0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.3543    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.2595    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    0.0151    1.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823    0.7212    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    4.5604   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    4.3125    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    4.6214    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422    2.7468    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.7109    0.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3392   -1.6606    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -3.8996    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.9638   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -1.6589   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -3.3719   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5463    0.1851    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -1.2537    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493    0.3901   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    1.7710    0.0379 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 13  3  1  0
 21 14  1  0
 12  6  1  0
 21 18  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
M  END

  Mrv0541 05061307212D          

 21 24  0  0  0  0            999 V2000
    2.5382    1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174    2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232    5.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0642    5.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    4.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    5.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162    5.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    3.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    4.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    1.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    4.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2723    3.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    4.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15  1  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033783

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-15-13(21-15)12(20-14(15)17)10-8(18-2)5-3-7-4-6-9(16)19-11(7)10/h3-6,12-14,17H,1-2H3

> <INCHI_KEY>
VUIRVFUCVWAGFV-UHFFFAOYSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.88626989245251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.2070936276666668

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.161791599547911

> <JCHEM_PKA_STRONGEST_BASIC>
-3.978864589409231

> <JCHEM_POLAR_SURFACE_AREA>
77.52000000000001

> <JCHEM_REFRACTIVITY>
71.36310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033783
     RDKit          3D
Marshrin
 35 38  0  0  0  0  0  0  0  0999 V2000
    0.7489    4.0846   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    2.7474   -0.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    1.6405   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4793    1.7676    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859    0.6142    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161   -0.6293    0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -1.7573    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -3.0018    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -3.0317    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9524   -4.1666   -0.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401   -1.9069   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -0.7191   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    0.3999   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102    0.3892   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.9565   -1.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.4258   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -2.5882   -0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.3543    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.2595    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    0.0151    1.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823    0.7212    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    4.5604   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    4.3125    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    4.6214    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422    2.7468    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.7109    0.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3392   -1.6606    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -3.8996    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.9638   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -1.6589   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -3.3719   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5463    0.1851    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -1.2537    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493    0.3901   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    1.7710    0.0379 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 13  3  1  0
 21 14  1  0
 12  6  1  0
 21 18  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.738   2.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.366   4.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.257   9.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.720  10.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.287   8.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.213  10.412   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.750   9.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.811   7.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.738   8.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.305   6.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.274   8.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.829   5.514   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.364   5.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.829   3.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.364   3.498   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.231   8.627   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.305   1.558   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.842   6.155   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.768   7.803   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.734   4.268   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.031   4.268   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   18                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3    4   11                                                  
CONECT    8    5   10   18                                                  
CONECT    9    6   16   19                                                  
CONECT   10    8   11   12                                                  
CONECT   11    7   10   19                                                  
CONECT   12   10   13   20                                                  
CONECT   13   12   15   21                                                  
CONECT   14   15   17   20                                                  
CONECT   15    1   13   14   21                                             
CONECT   16    9                                                            
CONECT   17   14                                                            
CONECT   18    2    8                                                       
CONECT   19    9   11                                                       
CONECT   20   12   14                                                       
CONECT   21   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0033783
HETATM    1  C1  UNL     1       0.749   4.085  -0.251  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.411   2.747  -0.364  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.189   1.640  -0.086  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.479   1.768   0.361  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.186   0.614   0.617  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.616  -0.629   0.430  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.344  -1.757   0.679  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.792  -3.002   0.485  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.496  -3.032   0.037  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.952  -4.167  -0.151  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.840  -1.907  -0.185  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.294  -0.719  -0.027  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.553   0.400  -0.295  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.810   0.389  -0.911  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.026  -0.957  -1.289  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.190  -1.426  -0.788  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.979  -2.588  -0.029  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.784  -0.354   0.109  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.247  -0.259   0.310  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.000   0.015   1.229  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.882   0.721   0.052  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.516   4.560  -1.253  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.778   4.312   0.004  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.127   4.621   0.528  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.942   2.747   0.511  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.207   0.711   0.980  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.339  -1.661   1.040  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.359  -3.900   0.666  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.824   0.964  -1.830  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.934  -1.659  -1.567  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.174  -3.372  -0.559  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.546   0.185   1.277  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.720  -1.254   0.243  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.749   0.390  -0.454  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.302   1.771   0.038  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   12
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   21   29
CONECT   15   16
CONECT   16   17   18   30
CONECT   17   31
CONECT   18   19   20   21
CONECT   19   32   33   34
CONECT   20   21
CONECT   21   35
END

HMDB0033783
     RDKit          3D
Marshrin
 35 38  0  0  0  0  0  0  0  0999 V2000
    0.7489    4.0846   -0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    2.7474   -0.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    1.6405   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4793    1.7676    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859    0.6142    0.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161   -0.6293    0.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -1.7573    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -3.0018    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -3.0317    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9524   -4.1666   -0.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401   -1.9069   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -0.7191   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    0.3999   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102    0.3892   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.9565   -1.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.4258   -0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -2.5882   -0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.3543    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.2595    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    0.0151    1.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823    0.7212    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    4.5604   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    4.3125    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    4.6214    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422    2.7468    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.7109    0.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3392   -1.6606    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -3.8996    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.9638   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -1.6589   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -3.3719   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5463    0.1851    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -1.2537    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493    0.3901   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    1.7710    0.0379 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 13  3  1  0
 21 14  1  0
 12  6  1  0
 21 18  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₆

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

IUPAC Name

8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxy-2H-chromen-2-one

Traditional Name

8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C15H14O6/c1-15-13(21-15)12(20-14(15)17)10-8(18-2)5-3-7-4-6-9(16)19-11(7)10/h3-6,12-14,17H,1-2H3

InChI Key

VUIRVFUCVWAGFV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Para-dioxane
Benzenoid
Pyran
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Hemiacetal
Lactone
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033783)
Cytoplasm (HMDB: HMDB0033783)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033783)

Source

Exogenous

Exogenous (HMDB: HMDB0033783)

Food

Food (HMDB: HMDB0033783)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0033783)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033783)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 203 °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	1.65 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.21	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.16	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.36 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	4	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]+	165.53	31661259
DarkChem	[M-H]-	164.033	31661259
DeepCCS	[M-2H]-	205.918	30932474
DeepCCS	[M+Na]+	181.783	30932474
AllCCS	[M+H]+	165.7	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	169.1	32859911
AllCCS	[M+Na]+	170.1	32859911
AllCCS	[M-H]-	170.0	32859911
AllCCS	[M+Na-2H]-	169.4	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marshrin	COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1	3468.7	Standard polar	33892256
Marshrin	COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1	2381.8	Standard non polar	33892256
Marshrin	COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1	2582.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Marshrin,1TMS,isomer #1	COC1=CC=C2C=CC(=O)OC2=C1C1OC(O[Si](C)(C)C)C2(C)OC12	2427.2	Semi standard non polar	33892256
Marshrin,1TBDMS,isomer #1	COC1=CC=C2C=CC(=O)OC2=C1C1OC(O[Si](C)(C)C(C)(C)C)C2(C)OC12	2676.4	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 - Marshrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbc-5090000000-0643767d56d6942fa0c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marshrin GC-MS (1 TMS) - 70eV, Positive	splash10-0fgc-9153000000-953d329774dfd34420f1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marshrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marshrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Marshrin 10V, Positive-QTOF	splash10-0006-0090000000-615f8ce217d9d2c4c9b3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 20V, Positive-QTOF	splash10-00r6-0390000000-ea6b58f1e71cc0fa2a1a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 40V, Positive-QTOF	splash10-0a4l-1890000000-4af2a6dc5ff6aabfa699	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 10V, Negative-QTOF	splash10-000i-0190000000-de921fd7bee682ec65e8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 20V, Negative-QTOF	splash10-0079-0290000000-1db0c4afb5e3727a0ea2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 40V, Negative-QTOF	splash10-0arr-4960000000-d509d7206901cccacaa8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 10V, Negative-QTOF	splash10-000i-0190000000-95912fc4e8a2868727f8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 20V, Negative-QTOF	splash10-000i-0090000000-e2151ad40a991fb233bc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 40V, Negative-QTOF	splash10-000i-1790000000-9911b60df75e4e924e98	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 10V, Positive-QTOF	splash10-0006-0190000000-eeb99073b090db72bbe0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 20V, Positive-QTOF	splash10-0006-0390000000-ba74e75da0070996f981	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marshrin 40V, Positive-QTOF	splash10-009f-1690000000-a128887864ac98f36861	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

FDB011941

KNApSAcK ID

Not Available

Chemspider ID

35013666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73193397

PDB ID

Not Available

ChEBI ID

Not Available

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.. .

Showing metabocard for Marshrin (HMDB0033783)

MOL for HMDB0033783 (Marshrin)

3D MOL for HMDB0033783 (Marshrin)

3D SDF for HMDB0033783 (Marshrin)

3D-SDF for HMDB0033783 (Marshrin)

PDB for HMDB0033783 (Marshrin)

3D PDB for HMDB0033783 (Marshrin)

SMILES for HMDB0033783 (Marshrin)

INCHI for HMDB0033783 (Marshrin)

Structure for HMDB0033783 (Marshrin)

3D Structure for HMDB0033783 (Marshrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra