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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:25 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030853

Secondary Accession Numbers

HMDB30853

Metabolite Identification

Common Name

(R)-Meranzin

Description

(R)-Meranzin 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) (R)-Meranzin is a bitter tasting compound (R)-Meranzin has been detected, but not quantified in, sweet oranges (Citrus sinensis). This could make (R)-meranzin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-Meranzin.

Structure

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

HMDB0030853
     RDKit          3D
(R)-Meranzin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.2598    3.2934    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    2.0191    0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    1.1367    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.4963    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    0.6238    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -0.6164    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664   -1.4843    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -2.7216   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -3.0165   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079   -4.1626   -1.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -2.1573   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -0.9633   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -0.1046   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.5139   -1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -0.8930   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -1.2878   -1.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8796   -0.1849   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400   -0.6303    1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    1.0860   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    3.8676    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    3.1725    1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    3.8484    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    2.4858    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.9299    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -1.2175    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -3.4150   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -1.4012   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    0.2861   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -1.7430    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.2732    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368    0.2984    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -1.0625    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    1.1734   -1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4703    1.1357   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939    1.9958   -0.2342 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
 17 18  1  0
 17 19  1  0
 13  3  1  0
 17 15  1  0
 12  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

  Mrv0541 05061305332D          

 19 21  0  0  0  0            999 V2000
   -0.4950    4.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    4.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   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
    1.4289    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17  3  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030853

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-15(2)12(19-15)8-10-11(17-3)6-4-9-5-7-13(16)18-14(9)10/h4-7,12H,8H2,1-3H3

> <INCHI_KEY>
LSZONYLDFHGRDP-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.329896674473765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.375520110666667

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.128831262558024

> <JCHEM_POLAR_SURFACE_AREA>
48.06

> <JCHEM_REFRACTIVITY>
71.09210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030853
     RDKit          3D
(R)-Meranzin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.2598    3.2934    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    2.0191    0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    1.1367    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.4963    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    0.6238    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -0.6164    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664   -1.4843    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -2.7216   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -3.0165   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079   -4.1626   -1.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -2.1573   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -0.9633   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -0.1046   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.5139   -1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -0.8930   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -1.2878   -1.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8796   -0.1849   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400   -0.6303    1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    1.0860   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    3.8676    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    3.1725    1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    3.8484    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    2.4858    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.9299    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -1.2175    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -3.4150   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -1.4012   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    0.2861   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -1.7430    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.2732    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368    0.2984    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -1.0625    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    1.1734   -1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4703    1.1357   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939    1.9958   -0.2342 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
 17 18  1  0
 17 19  1  0
 13  3  1  0
 17 15  1  0
 12  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 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      -0.924   9.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.283   9.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.104   8.264   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.874   6.930   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   17                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8   10   12                                                       
CONECT    9    4    5   14                                                  
CONECT   10    8   11   14                                                  
CONECT   11    6   10   17                                                  
CONECT   12    8   15   19                                                  
CONECT   13    7   16   18                                                  
CONECT   14    9   10   18                                                  
CONECT   15    1    2   12   19                                             
CONECT   16   13                                                            
CONECT   17    3   11                                                       
CONECT   18   13   14                                                       
CONECT   19   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0254460
HETATM    1  C1  UNL     1      -0.351  -3.494  -1.132  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.079  -2.419  -0.267  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.835  -1.287  -0.114  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.994  -1.176  -0.887  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.782  -0.061  -0.768  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.435   0.935   0.101  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.262   2.037   0.183  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.901   3.032   1.063  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.745   2.856   1.794  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.441   3.787   2.592  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.990   1.773   1.671  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.288   0.800   0.852  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.469  -0.292   0.770  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.732  -0.415   1.564  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.046  -0.141   0.947  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.084   1.283   0.468  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.471   0.109  -0.352  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.746   0.113  -1.653  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.996   0.210  -0.579  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.609  -4.086  -1.185  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.626  -3.183  -2.158  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.143  -4.175  -0.722  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.242  -1.979  -1.566  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.691   0.041  -1.365  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.172   2.131  -0.418  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.508   3.928   1.177  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.664   0.250   2.486  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.825  -1.441   2.048  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.852  -0.208   1.748  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.305   0.802  -2.369  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.732   0.525  -1.651  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.810  -0.918  -2.083  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.538  -0.221   0.297  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.293   1.265  -0.739  1.00  0.00           H  
HETATM   35  H16 UNL     1       4.251  -0.381  -1.479  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   12
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   27   28
CONECT   15   16   17   29
CONECT   16   17
CONECT   17   18   19
CONECT   18   30   31   32
CONECT   19   33   34   35
END

HMDB0030853
     RDKit          3D
(R)-Meranzin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -0.2598    3.2934    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    2.0191    0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    1.1367    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.4963    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    0.6238    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -0.6164    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664   -1.4843    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -2.7216   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -3.0165   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079   -4.1626   -1.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -2.1573   -0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -0.9633   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -0.1046   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.5139   -1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -0.8930   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -1.2878   -1.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8796   -0.1849   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400   -0.6303    1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    1.0860   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    3.8676    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    3.1725    1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    3.8484    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    2.4858    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.9299    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -1.2175    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -3.4150   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -1.4012   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    0.2861   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -1.7430    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.2732    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368    0.2984    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -1.0625    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    1.1734   -1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4703    1.1357   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939    1.9958   -0.2342 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
 17 18  1  0
 17 19  1  0
 13  3  1  0
 17 15  1  0
 12  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxy-2H-chromen-2-one

Traditional Name

8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C15H16O4/c1-15(2)12(19-15)8-10-11(17-3)6-4-9-5-7-13(16)18-14(9)10/h4-7,12H,8H2,1-3H3

InChI Key

LSZONYLDFHGRDP-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
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254460)

Food

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	98 °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	0.048 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.38	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.09 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.425	31661259
DarkChem	[M-H]-	158.731	31661259
DeepCCS	[M+H]+	166.856	30932474
DeepCCS	[M-H]-	164.498	30932474
DeepCCS	[M-2H]-	197.384	30932474
DeepCCS	[M+Na]+	172.949	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.1	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Meranzin	COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1	2885.9	Standard polar	33892256
(R)-Meranzin	COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1	2173.5	Standard non polar	33892256
(R)-Meranzin	COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1	2255.7	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 - (R)-Meranzin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdp-8490000000-04e17c594e4c44333143	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Meranzin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Meranzin 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 - (R)-Meranzin 10V, Positive-QTOF	splash10-03di-0090000000-ec2f14610581d133c66a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Positive-QTOF	splash10-0udi-5090000000-9814add42d4e72ab456e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Positive-QTOF	splash10-0079-1940000000-a23745f83dfd6d817275	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Negative-QTOF	splash10-0a4i-1090000000-c98d2fb299f4b1663942	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Negative-QTOF	splash10-056r-2890000000-5ce8f7cb7117f22853a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Negative-QTOF	splash10-00l7-9640000000-4e7acc3b4e57d93babdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Positive-QTOF	splash10-000i-0940000000-3f58cc96dd132eb95dcd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Positive-QTOF	splash10-0f79-1790000000-c1bbe0507dcee5edb49a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Positive-QTOF	splash10-0udi-4980000000-e2988a7762a591c4fd11	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Negative-QTOF	splash10-0a4i-0090000000-0647274cebfb179dc5a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Negative-QTOF	splash10-056r-1490000000-8fec533c8ebbc7ca97d0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Negative-QTOF	splash10-05o3-9560000000-3b216d03b9c037da1b7e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021654

KNApSAcK ID

Not Available

Chemspider ID

3045741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3819217

PDB ID

Not Available

ChEBI ID

174412

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. Glutathione S-transferase P

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:: GSTP1
Uniprot ID:: P09211
Molecular weight:: 23355.625

Reactions

(R)-Meranzin → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[3-hydroxy-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbutan-2-yl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic acid	details

Showing metabocard for (R)-Meranzin (HMDB0030853)

MOL for HMDB0030853 ((R)-Meranzin)

3D MOL for HMDB0030853 ((R)-Meranzin)

3D SDF for HMDB0030853 ((R)-Meranzin)

3D-SDF for HMDB0030853 ((R)-Meranzin)

PDB for HMDB0030853 ((R)-Meranzin)

3D PDB for HMDB0030853 ((R)-Meranzin)

SMILES for HMDB0030853 ((R)-Meranzin)

INCHI for HMDB0030853 ((R)-Meranzin)

Structure for HMDB0030853 ((R)-Meranzin)

3D Structure for HMDB0030853 ((R)-Meranzin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions