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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:02 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030788

Secondary Accession Numbers

HMDB30788

Metabolite Identification

Common Name

Citrusal

Description

Citrusal 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). Based on a literature review very few articles have been published on Citrusal.

Structure

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

HMDB0030788
     RDKit          3D
Citrusal
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.0986    4.2020   -0.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1713    2.8709   -0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.8126   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354    2.0384   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9446    1.0082   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591   -0.2683   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278   -1.3467   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402   -2.6099    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -2.7333    0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -3.9095    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.6847    0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -0.4769    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949    0.5299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    0.4589    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -0.8107    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -1.7938   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459   -0.4814    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -1.4877    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9688   -2.6486    1.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316    4.7118   -1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    4.3712   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    4.7326    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    3.0363   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943    1.1696   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3913   -1.1358   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -3.4265    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0966    1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    1.0497   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -2.8375   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -1.9331   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -1.4545   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.0305   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.4027    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6548    0.2418    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -0.9193    2.4157 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
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  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
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
M  END

  Mrv0541 05061305302D          

 19 20  0  0  0  0            999 V2000
    1.1270    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.4270    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
    1.4289    4.1250    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
    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
   -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
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030788

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
VCYVDHAWDPDCKW-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.914291157986383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanal

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.648389632

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.83744461903377

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
72.07050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(7-methoxy-2-oxochromen-8-yl)-2,2-dimethylpropanal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030788
     RDKit          3D
Citrusal
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.0986    4.2020   -0.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1713    2.8709   -0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.8126   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354    2.0384   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9446    1.0082   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591   -0.2683   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278   -1.3467   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402   -2.6099    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -2.7333    0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -3.9095    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.6847    0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -0.4769    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949    0.5299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    0.4589    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -0.8107    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -1.7938   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459   -0.4814    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -1.4877    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9688   -2.6486    1.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316    4.7118   -1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    4.3712   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    4.7326    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    3.0363   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943    1.1696   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3913   -1.1358   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -3.4265    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0966    1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    1.0497   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -2.8375   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -1.9331   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -1.4545   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.0305   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.4027    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6548    0.2418    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -0.9193    2.4157 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
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  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
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 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       2.104   5.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564   8.264   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       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   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   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   9.240   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      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   18                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   12                                                       
CONECT    7    5   13                                                       
CONECT    8   11   15                                                       
CONECT    9   15   16                                                       
CONECT   10    4    5   14                                                  
CONECT   11    8   12   14                                                  
CONECT   12    6   11   18                                                  
CONECT   13    7   17   19                                                  
CONECT   14   10   11   19                                                  
CONECT   15    1    2    8    9                                             
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18    3   12                                                       
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0030788
HETATM    1  C1  UNL     1       0.099   4.202  -0.609  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.171   2.871  -0.362  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.715   1.813  -0.287  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.035   2.038  -0.469  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.945   1.008  -0.400  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.459  -0.268  -0.137  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.328  -1.347  -0.055  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.840  -2.610   0.207  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.470  -2.733   0.378  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.056  -3.910   0.617  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.714  -1.685   0.288  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.104  -0.477   0.046  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.195   0.530  -0.020  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.240   0.459   0.155  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.936  -0.811   0.313  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.825  -1.794  -0.826  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.446  -0.481   0.413  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.681  -1.488   1.635  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.969  -2.649   1.784  1.00  0.00           O  
HETATM   20  H1  UNL     1      -0.732   4.712  -1.184  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.059   4.371  -1.120  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.067   4.733   0.388  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.463   3.036  -0.678  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.994   1.170  -0.544  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.391  -1.136  -0.208  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.517  -3.427   0.266  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.469   1.097   1.069  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.779   1.050  -0.659  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.601  -2.837  -0.480  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.821  -1.933  -1.359  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.165  -1.454  -1.653  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.667   0.031  -0.560  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.047  -1.403   0.441  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.655   0.242   1.197  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.249  -0.919   2.416  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   18
CONECT   16   29   30   31
CONECT   17   32   33   34
CONECT   18   19   19   35
END

HMDB0030788
     RDKit          3D
Citrusal
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.0986    4.2020   -0.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1713    2.8709   -0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.8126   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354    2.0384   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9446    1.0082   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591   -0.2683   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278   -1.3467   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402   -2.6099    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -2.7333    0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -3.9095    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.6847    0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -0.4769    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949    0.5299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    0.4589    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -0.8107    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -1.7938   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459   -0.4814    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -1.4877    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9688   -2.6486    1.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316    4.7118   -1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    4.3712   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    4.7326    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    3.0363   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943    1.1696   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3913   -1.1358   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -3.4265    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.0966    1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    1.0497   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -2.8375   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -1.9331   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -1.4545   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.0305   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.4027    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6548    0.2418    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -0.9193    2.4157 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
 15 17  1  0
 15 18  1  0
 18 19  2  0
 13  3  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
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methoxy-8-(2-formyl-2-methylpropyl)coumarin	HMDB
8-(2,2-Dimethyl-3-oxopropyl)-7-methoxy-2H-1-benzopyran-2-one, 9ci	HMDB
Morphine sulfate (anhydrous)	HMDB
Morphine sulphate (anhydrous)	HMDB

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanal

Traditional Name

3-(7-methoxy-2-oxochromen-8-yl)-2,2-dimethylpropanal

CAS Registry Number

5980-07-4

SMILES

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

InChI Identifier

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

InChI Key

VCYVDHAWDPDCKW-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
Ether
Organoheterocyclic compound
Aldehyde
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030788)
Cell membrane (HMDB: HMDB0030788)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030788)

Source

Endogenous

Endogenous (HMDB: HMDB0030788)

Plant

Plant (HMDB: HMDB0030788)

Exogenous

Food

Food (HMDB: HMDB0030788)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0030788)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	137 - 138 °C	Not Available
Boiling Point	418.65 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	150.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.228 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.07 m³·mol⁻¹	ChemAxon
Polarizability	26.91 Å³	ChemAxon
Number of Rings	2	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]+	160.036	31661259
DarkChem	[M-H]-	160.84	31661259
DeepCCS	[M+H]+	168.334	30932474
DeepCCS	[M-H]-	165.976	30932474
DeepCCS	[M-2H]-	198.862	30932474
DeepCCS	[M+Na]+	174.427	30932474
AllCCS	[M+H]+	157.1	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.7	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrusal	COC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C1	2864.9	Standard polar	33892256
Citrusal	COC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C1	2179.9	Standard non polar	33892256
Citrusal	COC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C1	2173.9	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 - Citrusal GC-MS (Non-derivatized) - 70eV, Positive	splash10-003s-3590000000-b8baf4c20c82d8071831	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusal 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 - Citrusal 10V, Positive-QTOF	splash10-03di-0090000000-81a5d4c2650e11b1303a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 20V, Positive-QTOF	splash10-03di-1090000000-b068b8d4c13be2af4497	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 40V, Positive-QTOF	splash10-0g5c-5980000000-ed70c534a6372c60f306	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 10V, Negative-QTOF	splash10-0a4i-0090000000-a61e29c0a847fdab8698	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 20V, Negative-QTOF	splash10-0a4i-0090000000-b57d2d806e3f0cc265f2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 40V, Negative-QTOF	splash10-014j-9760000000-ee2a06d185d10f8b2d79	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 10V, Negative-QTOF	splash10-0a4i-0090000000-1048deeca0eebbf13448	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 20V, Negative-QTOF	splash10-0a4i-0490000000-93582fca3e3c14b5999b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 40V, Negative-QTOF	splash10-0229-0910000000-a7409ba6abb70a6dcf25	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 10V, Positive-QTOF	splash10-03du-0950000000-6208d893a59d744e9de3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 20V, Positive-QTOF	splash10-000i-0910000000-c71eb85b8e8edfaeb923	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusal 40V, Positive-QTOF	splash10-06y6-3910000000-d5da9e4f0a5a55a8d169	2021-09-25	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

FDB002726

KNApSAcK ID

C00054444

Chemspider ID

4477732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319433

PDB ID

Not Available

ChEBI ID

174411

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637241

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. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

Reactions

Citrusal → 8-(3-hydroxy-2,2-dimethylpropyl)-7-methoxy-2H-chromen-2-one	details

Enzyme Details

2. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Reactions

Citrusal → 3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanoic acid	details

Showing metabocard for Citrusal (HMDB0030788)

MOL for HMDB0030788 (Citrusal)

3D MOL for HMDB0030788 (Citrusal)

3D SDF for HMDB0030788 (Citrusal)

3D-SDF for HMDB0030788 (Citrusal)

PDB for HMDB0030788 (Citrusal)

3D PDB for HMDB0030788 (Citrusal)

SMILES for HMDB0030788 (Citrusal)

INCHI for HMDB0030788 (Citrusal)

Structure for HMDB0030788 (Citrusal)

3D Structure for HMDB0030788 (Citrusal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions