Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:30:51 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039146

Secondary Accession Numbers

HMDB39146

Metabolite Identification

Common Name

Citrubuntin

Description

Citrubuntin 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). Citrubuntin has been detected, but not quantified in, citrus. This could make citrubuntin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citrubuntin.

Structure

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

HMDB0039146
     RDKit          3D
Citrubuntin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.6895   -1.2282   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -0.2730   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    1.1324   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3466   -0.5583   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4674    0.3847   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.2739   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.4442   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162    1.3588   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801    2.5070   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536    2.4156    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8741    1.1911    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    1.0758    0.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1101    0.1246    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    0.1644    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -0.9696    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192   -0.9117   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596   -2.1080   -0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -3.3192    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7304   -0.9850   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.2816   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    1.6756    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913    1.2476   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    1.6348   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5849   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891    1.4099   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206    2.3847   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    3.4702   -0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    3.3132    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.9368    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -4.2020   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -3.4352   -0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -3.4147    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END


  Mrv0541 05061310532D          

 18 19  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    3.5724    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
    0.0000    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
    1.4289    0.8250    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
    4.2868    0.8250    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
    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
   -0.7145    2.0625    0.0000 C   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
    2.8579    2.4750    0.0000 O   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
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 16 15  2  0  0  0  0
 17  3  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039146

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=CC(=O)O2)C=C1\C=C\C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4-9H,1H2,2-3H3/b5-4+

> <INCHI_KEY>
GHVNFLHFOPJJNP-SNAWJCMRSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.2699

> <EXACT_MASS>
242.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.37480277576074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-6-[(1E)-3-methylbuta-1,3-dien-1-yl]-2H-chromen-2-one

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.1329673626666668

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.847001465487572

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
72.29870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-6-[(1E)-3-methylbuta-1,3-dien-1-yl]chromen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0039146
     RDKit          3D
Citrubuntin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.6895   -1.2282   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -0.2730   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    1.1324   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3466   -0.5583   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4674    0.3847   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.2739   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.4442   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162    1.3588   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801    2.5070   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536    2.4156    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8741    1.1911    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    1.0758    0.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1101    0.1246    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    0.1644    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -0.9696    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192   -0.9117   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596   -2.1080   -0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -3.3192    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7304   -0.9850   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.2816   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    1.6756    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913    1.2476   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    1.6348   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5849   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891    1.4099   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206    2.3847   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    3.4702   -0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    3.3132    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.9368    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -4.2020   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -3.4352   -0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -3.4147    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   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       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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   17                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   15                                                       
CONECT    8   11   12                                                       
CONECT    9   13   14                                                       
CONECT   10    1    2    4                                                  
CONECT   11    5    8   13                                                  
CONECT   12    6    8   14                                                  
CONECT   13    9   11   17                                                  
CONECT   14    9   12   18                                                  
CONECT   15    7   16   18                                                  
CONECT   16   15                                                            
CONECT   17    3   13                                                       
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0039146
HETATM    1  C1  UNL     1       4.689  -1.228  -0.410  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.791  -0.273  -0.385  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.218   1.132  -0.464  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.347  -0.558  -0.280  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.467   0.385  -0.256  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.046   0.274  -0.158  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.751   1.444  -0.148  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.116   1.359  -0.055  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.880   2.507  -0.046  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.254   2.416   0.048  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.874   1.191   0.133  1.00  0.00           C  
HETATM   12  O1  UNL     1      -6.133   1.076   0.220  1.00  0.00           O  
HETATM   13  O2  UNL     1      -4.110   0.125   0.121  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.792   0.164   0.033  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.024  -0.970   0.023  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.619  -0.912  -0.072  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.060  -2.108  -0.073  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.645  -3.319   0.017  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.730  -0.985  -0.487  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.440  -2.282  -0.355  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.053   1.676   0.510  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.291   1.248  -0.690  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.670   1.635  -1.288  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.058  -1.585  -0.224  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.889   1.410  -0.320  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.221   2.385  -0.217  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.366   3.470  -0.115  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.851   3.313   0.055  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.513  -1.937   0.090  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.018  -4.202  -0.085  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.424  -3.435  -0.770  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.194  -3.415   0.991  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    4
CONECT    3   21   22   23
CONECT    4    5    5   24
CONECT    5    6   25
CONECT    6    7    7   16
CONECT    7    8   26
CONECT    8    9   14   14
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   29
CONECT   16   17
CONECT   17   18
CONECT   18   30   31   32
END

HMDB0039146
     RDKit          3D
Citrubuntin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.6895   -1.2282   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -0.2730   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177    1.1324   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3466   -0.5583   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4674    0.3847   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.2739   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.4442   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162    1.3588   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801    2.5070   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536    2.4156    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8741    1.1911    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    1.0758    0.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1101    0.1246    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    0.1644    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -0.9696    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192   -0.9117   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596   -2.1080   -0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -3.3192    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7304   -0.9850   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.2816   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    1.6756    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913    1.2476   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    1.6348   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582   -1.5849   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891    1.4099   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206    2.3847   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    3.4702   -0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    3.3132    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.9368    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -4.2020   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -3.4352   -0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -3.4147    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  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  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methoxy-6-(3-methyl-1,3-butadienyl)-2H-1-benzopyran-2-one, 9ci	HMDB
Dehydrosuberosin	HMDB
Suberodiene	HMDB

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.2699

Monoisotopic Molecular Weight

242.094294314

IUPAC Name

7-methoxy-6-[(1E)-3-methylbuta-1,3-dien-1-yl]-2H-chromen-2-one

Traditional Name

7-methoxy-6-[(1E)-3-methylbuta-1,3-dien-1-yl]chromen-2-one

CAS Registry Number

74794-83-5

SMILES

COC1=CC2=C(C=CC(=O)O2)C=C1\C=C\C(C)=C

InChI Identifier

InChI=1S/C15H14O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4-9H,1H2,2-3H3/b5-4+

InChI Key

GHVNFLHFOPJJNP-SNAWJCMRSA-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
Styrene
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039146)

Cellular substructure

Membrane (HMDB: HMDB0039146)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039146)

Source

Exogenous

Food

Food (HMDB: HMDB0039146)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0039146)

Not Available

Nutrient (HMDB: HMDB0039146)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 120 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	14.54 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.3 m³·mol⁻¹	ChemAxon
Polarizability	26.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.566	31661259
DarkChem	[M-H]-	160.142	31661259
DeepCCS	[M+H]+	160.3	30932474
DeepCCS	[M-H]-	157.942	30932474
DeepCCS	[M-2H]-	190.828	30932474
DeepCCS	[M+Na]+	166.393	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.6	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.5	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	156.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrubuntin	COC1=CC2=C(C=CC(=O)O2)C=C1\C=C\C(C)=C	3031.9	Standard polar	33892256
Citrubuntin	COC1=CC2=C(C=CC(=O)O2)C=C1\C=C\C(C)=C	2197.4	Standard non polar	33892256
Citrubuntin	COC1=CC2=C(C=CC(=O)O2)C=C1\C=C\C(C)=C	2393.2	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 - Citrubuntin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0970000000-efd11e7904b6b82f3687	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrubuntin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrubuntin 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 - Citrubuntin 10V, Positive-QTOF	splash10-0006-0090000000-b723f38a9af0d9dc6071	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 20V, Positive-QTOF	splash10-0006-2290000000-bd90d278be209b145d42	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 40V, Positive-QTOF	splash10-0gi3-5940000000-af1ab49dcb9a3ee10516	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 10V, Negative-QTOF	splash10-0006-0190000000-e477207588c12b95e668	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 20V, Negative-QTOF	splash10-0006-0490000000-3d30c3a378d9d9965dc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 40V, Negative-QTOF	splash10-003r-1920000000-26477ee6b08e64f12a60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 10V, Negative-QTOF	splash10-0006-0090000000-b72122e63043a3d3aeba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 20V, Negative-QTOF	splash10-002o-0190000000-04cbe7c75a653b5af31a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 40V, Negative-QTOF	splash10-000i-0950000000-4008bbe194fb9515bc05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 10V, Positive-QTOF	splash10-0006-0090000000-a810a7788942d2c00b91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 20V, Positive-QTOF	splash10-0006-0090000000-93d7d82a198be67026af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrubuntin 40V, Positive-QTOF	splash10-0005-2910000000-a096bbe461b97acd7ec7	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

FDB018666

KNApSAcK ID

C00019813

Chemspider ID

30777330

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14077807

PDB ID

Not Available

ChEBI ID

173747

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1874661

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 Citrubuntin (HMDB0039146)

MOL for HMDB0039146 (Citrubuntin)

3D MOL for HMDB0039146 (Citrubuntin)

3D SDF for HMDB0039146 (Citrubuntin)

3D-SDF for HMDB0039146 (Citrubuntin)

PDB for HMDB0039146 (Citrubuntin)

3D PDB for HMDB0039146 (Citrubuntin)

SMILES for HMDB0039146 (Citrubuntin)

INCHI for HMDB0039146 (Citrubuntin)

Structure for HMDB0039146 (Citrubuntin)

3D Structure for HMDB0039146 (Citrubuntin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra