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Showing metabocard for Citropten (HMDB0032952)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:53 UTC
Update Date2023-02-21 17:22:51 UTC
HMDB IDHMDB0032952
Secondary Accession Numbers
  • HMDB32952
Metabolite Identification
Common NameCitropten
DescriptionCitropten 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). Citropten has been detected, but not quantified in, a few different foods, such as citrus, lemons (Citrus limon), and limes (Citrus aurantiifolia). This could make citropten a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Citropten.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032952 (Citropten)

  Mrv0541 05061306492D          

 15 16  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.5724    1.2375    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
  4  3  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032952 (Citropten)

HMDB0032952
     RDKit          3D
Citropten
 25 26  0  0  0  0  0  0  0  0999 V2000
    3.9235   -0.0993    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8121   -0.9532    0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -0.4692    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -1.3445   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -0.8746   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220   -1.7107   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -3.0931   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223    0.4795    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2941    1.0156    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653    2.3766    0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676    3.1858    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664    4.4172    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669    2.6509    0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342    1.3569    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    0.8838    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8564   -0.6844    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458    0.3910    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664    0.6793   -0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -2.3857   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -3.2813   -1.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -3.6319   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710   -3.5600    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166    0.3256   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    2.7394    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    1.5863    0.4126 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15  3  1  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 15 25  1  0
M  END
Download

3D SDF for HMDB0032952 (Citropten)

  Mrv0541 05061306492D          

 15 16  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.5724    1.2375    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
  4  3  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032952

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

> <INCHI_KEY>
NXJCRELRQHZBQA-UHFFFAOYSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.1947

> <EXACT_MASS>
206.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.36190716820778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.4680170839999995

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5508691816281095

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
54.475000000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
limettin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0032952 (Citropten)

HMDB0032952
     RDKit          3D
Citropten
 25 26  0  0  0  0  0  0  0  0999 V2000
    3.9235   -0.0993    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8121   -0.9532    0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -0.4692    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -1.3445   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -0.8746   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220   -1.7107   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -3.0931   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223    0.4795    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2941    1.0156    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653    2.3766    0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676    3.1858    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664    4.4172    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669    2.6509    0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342    1.3569    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    0.8838    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8564   -0.6844    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458    0.3910    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664    0.6793   -0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -2.3857   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -3.2813   -1.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -3.6319   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710   -3.5600    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166    0.3256   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    2.7394    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    1.5863    0.4126 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15  3  1  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 15 25  1  0
M  END
Download

PDB for HMDB0032952 (Citropten)

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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   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  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    7    9                                                       
CONECT    6    7   10                                                       
CONECT    7    5    6   13                                                  
CONECT    8    3    9   10                                                  
CONECT    9    5    8   14                                                  
CONECT   10    6    8   15                                                  
CONECT   11    4   12   15                                                  
CONECT   12   11                                                            
CONECT   13    1    7                                                       
CONECT   14    2    9                                                       
CONECT   15   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for HMDB0032952 (Citropten)

COMPND    HMDB0032952
HETATM    1  C1  UNL     1       3.923  -0.099   0.304  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.812  -0.953   0.117  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.519  -0.469   0.098  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.470  -1.345  -0.087  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.837  -0.875  -0.110  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.922  -1.711  -0.292  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.834  -3.093  -0.470  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.022   0.479   0.059  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.294   1.016   0.047  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.465   2.377   0.218  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.368   3.186   0.397  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.566   4.417   0.548  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.167   2.651   0.404  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.034   1.357   0.244  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.325   0.884   0.265  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.856  -0.684   0.283  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.846   0.391   1.305  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.966   0.679  -0.489  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.676  -2.386  -0.213  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.790  -3.281  -1.578  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.737  -3.632  -0.061  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.971  -3.560   0.048  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.117   0.326  -0.098  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.484   2.739   0.200  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.146   1.586   0.413  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   19
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   20   21   22
CONECT    8    9   14
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   15
CONECT   15   25
END
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SMILES for HMDB0032952 (Citropten)

COC1=CC(OC)=C2C=CC(=O)OC2=C1
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INCHI for HMDB0032952 (Citropten)

InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
57-DimethoxycoumarinChEMBL, HMDB
5, 7-DimethoxycoumarinHMDB
5,7-Dimethoxy-2-benzopyroneHMDB
5,7-Dimethoxy-2H-1-benzo-pyran-2-oneHMDB
5,7-Dimethoxy-2H-1-benzopyran-2-oneHMDB
5,7-Dimethoxy-2H-chromen-2-oneHMDB
5,7-Dimethoxy-coumarinHMDB
5,7-DimethoxycoumarinHMDB
5,7-Dimethyloxy-2H-1-benzopyran-2-oneHMDB
CitrapteneHMDB
CitropteneHMDB
LimetinHMDB
LimettinHMDB, MeSH
OmphamurrayinMeSH, HMDB
CitroptenMeSH
Chemical FormulaC11H10O4
Average Molecular Weight206.1947
Monoisotopic Molecular Weight206.057908808
IUPAC Name5,7-dimethoxy-2H-chromen-2-one
Traditional Namelimettin
CAS Registry Number487-06-9
SMILES
COC1=CC(OC)=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3
InChI KeyNXJCRELRQHZBQA-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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling Point388.14 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1510 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.891 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.276http://allccs.zhulab.cn/database/detail?ID=AllCCS00001435
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010938
KNApSAcK IDNot Available
Chemspider ID2673
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitropten
METLIN IDNot Available
PubChem Compound2775
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1208211
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .