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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:42:19 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033931

Secondary Accession Numbers

HMDB33931

Metabolite Identification

Common Name

Xanthoxyletin

Description

Xanthoxyletin belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthoxyletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Xanthoxyletin has also been detected, but not quantified in, a few different foods, such as herbs and spices, lemons (Citrus limon), and mandarin orange (clementine, tangerine). This could make xanthoxyletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthoxyletin.

Structure

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

HMDB0033931
     RDKit          3D
Xanthoxyletin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8019    2.9274    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    2.0995   -0.4559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    0.7820   -0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    0.4198   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868   -0.9265   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987   -1.8984   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -1.5202   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4924   -0.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -2.2023   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -3.1195   -0.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4342   -0.8918   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    0.1415   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -0.1974   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8218   -1.2606   -0.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -0.3431   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -0.6648   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -0.5549    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    1.0677   -0.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762    1.4144   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327    2.7113    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    2.7017    1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    3.9870    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.9278   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5024   -0.6453   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8046    1.1675   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194   -0.7205   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -1.6802   -1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249    0.1199   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.0360    1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460    0.4164    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.2388    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.8883   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    2.4760   -0.5067 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  1  0
 19  4  1  0
 13  7  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
 11 24  1  0
 12 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv0541 05061307272D          

 19 21  0  0  0  0            999 V2000
   -1.5269    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.4623    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    1.4289    0.8250    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
    2.1434    1.2375    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
    3.5724    1.2375    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  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  7  1  0  0  0  0
 16 13  2  0  0  0  0
 17  3  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033931

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2

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

> <INCHI_KEY>
JSJIIHRNDMLJGK-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.900058372279297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.5263117516666664

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.596255419878281

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
72.40520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthoxyletin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033931
     RDKit          3D
Xanthoxyletin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8019    2.9274    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    2.0995   -0.4559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    0.7820   -0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    0.4198   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868   -0.9265   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987   -1.8984   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -1.5202   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4924   -0.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -2.2023   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -3.1195   -0.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4342   -0.8918   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    0.1415   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -0.1974   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8218   -1.2606   -0.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -0.3431   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -0.6648   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -0.5549    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    1.0677   -0.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762    1.4144   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327    2.7113    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    2.7017    1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    3.9870    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.9278   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5024   -0.6453   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8046    1.1675   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194   -0.7205   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -1.6802   -1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249    0.1199   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.0360    1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460    0.4164    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.2388    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.8883   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    2.4760   -0.5067 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  1  0
 19  4  1  0
 13  7  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
 11 24  1  0
 12 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  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      -2.850   2.577   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.860   0.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   17                                                            
CONECT    4    5    9                                                       
CONECT    5    4   13                                                       
CONECT    6    7   10                                                       
CONECT    7    6   15                                                       
CONECT    8   11   12                                                       
CONECT    9    4   11   14                                                  
CONECT   10    6   12   14                                                  
CONECT   11    8    9   18                                                  
CONECT   12    8   10   19                                                  
CONECT   13    5   16   18                                                  
CONECT   14    9   10   17                                                  
CONECT   15    1    2    7   19                                             
CONECT   16   13                                                            
CONECT   17    3   14                                                       
CONECT   18   11   13                                                       
CONECT   19   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033931
HETATM    1  C1  UNL     1      -1.802   2.927   0.661  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.592   2.100  -0.456  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.205   0.782  -0.379  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.115   0.420  -0.371  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.487  -0.927  -0.291  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.499  -1.898  -0.220  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.829  -1.520  -0.229  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.743  -2.492  -0.159  1.00  0.00           O  
HETATM    9  C7  UNL     1      -4.014  -2.202  -0.163  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.895  -3.120  -0.096  1.00  0.00           O  
HETATM   11  C8  UNL     1      -4.434  -0.892  -0.239  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.529   0.142  -0.313  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.173  -0.197  -0.307  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.822  -1.261  -0.285  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.870  -0.343  -0.354  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.618  -0.665  -1.661  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.843  -0.555   0.795  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.437   1.068  -0.436  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.176   1.414  -0.444  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.033   2.711   1.437  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.785   2.702   1.166  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.822   3.987   0.361  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.192  -2.928  -0.160  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.502  -0.645  -0.243  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.805   1.168  -0.374  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.819  -0.720  -2.449  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.052  -1.680  -1.596  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.325   0.120  -1.930  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.330  -1.036   1.651  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.246   0.416   1.164  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.643  -1.239   0.454  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.170   1.888  -0.495  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.901   2.476  -0.507  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   19
CONECT    5    6    6   14
CONECT    6    7   23
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   14   15
CONECT   15   16   17   18
CONECT   16   26   27   28
CONECT   17   29   30   31
CONECT   18   19   19   32
CONECT   19   33
END

HMDB0033931
     RDKit          3D
Xanthoxyletin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.8019    2.9274    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    2.0995   -0.4559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    0.7820   -0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    0.4198   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868   -0.9265   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987   -1.8984   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -1.5202   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4924   -0.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -2.2023   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -3.1195   -0.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4342   -0.8918   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    0.1415   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -0.1974   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8218   -1.2606   -0.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -0.3431   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -0.6648   -1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -0.5549    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    1.0677   -0.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762    1.4144   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327    2.7113    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    2.7017    1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    3.9870    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.9278   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5024   -0.6453   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8046    1.1675   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194   -0.7205   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -1.6802   -1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249    0.1199   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.0360    1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460    0.4164    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.2388    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.8883   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    2.4760   -0.5067 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  1  0
 19  4  1  0
 13  7  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
 11 24  1  0
 12 25  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9ci	HMDB
5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one	HMDB
Xanthoxylin N	HMDB
Xanthoxyloin	HMDB
Xanthoxyletin	MeSH

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

5-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

Traditional Name

xanthoxyletin

CAS Registry Number

84-99-1

SMILES

COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2

InChI Identifier

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

InChI Key

JSJIIHRNDMLJGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:69929 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033931)

Cellular substructure

Membrane (HMDB: HMDB0033931)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033931)

Source

Exogenous

Food

Food (HMDB: HMDB0033931)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033931)

Process

Not Available

Role

Biological role

anti convulsant (HMDB: HMDB0033931)

Nutrient

Nutrient (HMDB: HMDB0033931)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	133 °C	Not Available
Boiling Point	438.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	40 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	3.640 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.53	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.41 m³·mol⁻¹	ChemAxon
Polarizability	26.9 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]+	160.609	31661259
DarkChem	[M-H]-	161.962	31661259
DeepCCS	[M+H]+	158.949	30932474
DeepCCS	[M-H]-	156.591	30932474
DeepCCS	[M-2H]-	189.477	30932474
DeepCCS	[M+Na]+	165.042	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.2	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	161.0	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthoxyletin	COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2	3028.6	Standard polar	33892256
Xanthoxyletin	COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2	2241.4	Standard non polar	33892256
Xanthoxyletin	COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2	2226.1	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 - Xanthoxyletin GC-MS (Non-derivatized) - 70eV, Positive	splash10-07ef-1190000000-78b72a1e70ea0b853ccc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthoxyletin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthoxyletin LC-ESI-qTof , Positive-QTOF	splash10-0uei-0940000000-f1e9eeeb83d8740504fc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthoxyletin , positive-QTOF	splash10-004i-0890000000-3a18d9c240e9f3626355	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthoxyletin , positive-QTOF	splash10-056r-0290000000-1de65956796614ac099e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Positive-QTOF	splash10-0a4i-0090000000-aa6d574f073513b5a829	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Positive-QTOF	splash10-0a4i-0090000000-6c6860209ee19099b43c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Positive-QTOF	splash10-0gi0-4890000000-1ab1343a5be832f0b76e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Negative-QTOF	splash10-0a4i-0090000000-573b07a2c6c0cb5cbcd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Negative-QTOF	splash10-0a4i-0090000000-fb78f7d59b6f70625682	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Negative-QTOF	splash10-01ow-0980000000-b3f729731c4334112db9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Positive-QTOF	splash10-0a4i-0090000000-5899da0eda98839d58ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Positive-QTOF	splash10-0a4i-0090000000-2cf3ccdcea338c77fa5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Positive-QTOF	splash10-0aou-1290000000-6d0938937a8c48a429ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Negative-QTOF	splash10-0a4i-0090000000-c2a50a42dfada53572a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Negative-QTOF	splash10-0aor-0090000000-bb952c86674434372ddd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Negative-QTOF	splash10-02ti-0290000000-4afb4baf58c4f7b7019a	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

FDB012133

KNApSAcK ID

C00032520

Chemspider ID

59919

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66548

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1540341

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 Xanthoxyletin (HMDB0033931)

MOL for HMDB0033931 (Xanthoxyletin)

3D MOL for HMDB0033931 (Xanthoxyletin)

3D SDF for HMDB0033931 (Xanthoxyletin)

3D-SDF for HMDB0033931 (Xanthoxyletin)

PDB for HMDB0033931 (Xanthoxyletin)

3D PDB for HMDB0033931 (Xanthoxyletin)

SMILES for HMDB0033931 (Xanthoxyletin)

INCHI for HMDB0033931 (Xanthoxyletin)

Structure for HMDB0033931 (Xanthoxyletin)

3D Structure for HMDB0033931 (Xanthoxyletin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra