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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:56:45 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034150

Secondary Accession Numbers

HMDB34150

Metabolite Identification

Common Name

Cernuine

Description

Cernuine belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Cernuine has been detected, but not quantified in, citrus and lemons (Citrus limon). This could make cernuine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cernuine.

Structure

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

HMDB0034150
     RDKit          3D
Cernuine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0871   -0.4041   -1.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.0860   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916    0.5141    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.8500    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    0.6553    0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    1.1587   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    0.9159   -1.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032    0.1408   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.1033   -1.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996   -0.3807    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -1.1657    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -0.1305    1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    0.6796    1.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.2182    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0297    0.1575    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.3651    0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -0.4257    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -0.8446   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.7824   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999   -1.2469   -2.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722   -0.2552   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060    1.2907    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901    1.7953   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    1.3358   -2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.2994   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0470   -1.3229    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5508    2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910    0.5352    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7253    0.3888   -0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0122   -1.2448   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.6263   -3.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  1  0
 10 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END


  Mrv0541 05061307372D          

 21 23  0  0  0  0            999 V2000
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  4  2  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 15  2  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034150

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4+

> <INCHI_KEY>
WBEFUVAYFSOUEA-YIXHJXPBSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.028014564623305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.6380130296666664

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.713611901859752

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.669575429612994

> <JCHEM_PKA_STRONGEST_BASIC>
-5.19380312967336

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
74.96990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034150
     RDKit          3D
Cernuine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0871   -0.4041   -1.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.0860   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916    0.5141    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.8500    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    0.6553    0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    1.1587   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    0.9159   -1.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032    0.1408   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.1033   -1.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996   -0.3807    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -1.1657    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -0.1305    1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    0.6796    1.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.2182    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0297    0.1575    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.3651    0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -0.4257    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -0.8446   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.7824   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999   -1.2469   -2.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722   -0.2552   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060    1.2907    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901    1.7953   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    1.3358   -2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.2994   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0470   -1.3229    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5508    2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910    0.5352    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7253    0.3888   -0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0122   -1.2448   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.6263   -3.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  1  0
 10 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  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      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.400   0.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.320   0.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.630  -1.158   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.090  -1.158   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.400  -2.492   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.320  -2.492   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   10                                                       
CONECT    4    7   13                                                       
CONECT    5    8   11                                                       
CONECT    6    8   12                                                       
CONECT    7    1    3    4                                                  
CONECT    8    5    6   16                                                  
CONECT    9    2   10   17                                                  
CONECT   10    3    9   18                                                  
CONECT   11    5   14   19                                                  
CONECT   12    6   14   21                                                  
CONECT   13    4   15   21                                                  
CONECT   14   11   12   15                                                  
CONECT   15   13   14   20                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   15                                                            
CONECT   21   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034150
HETATM    1  O1  UNL     1       0.087  -0.404  -1.207  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.715  -0.086  -0.297  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.392   0.514   0.978  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.798   0.850   1.433  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.004   0.655   0.666  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.237   1.159  -0.592  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.403   0.916  -1.302  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.403   0.141  -0.763  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.573  -0.103  -1.475  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.200  -0.381   0.504  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.217  -1.166   1.047  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.035  -0.131   1.196  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.611   0.680   1.655  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.659   0.218   0.871  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.030   0.157   1.074  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.820  -0.365   0.088  1.00  0.00           C  
HETATM   17  O5  UNL     1      -6.189  -0.426   0.290  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.332  -0.845  -1.118  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.965  -0.782  -1.316  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.400  -1.247  -2.507  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.172  -0.255  -0.320  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.806   1.291   2.443  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.490   1.795  -1.043  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.554   1.336  -2.308  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.677   0.299  -2.396  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.047  -1.323   0.511  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.895  -0.551   2.192  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.391   0.535   2.018  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.725   0.389  -0.013  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.012  -1.245  -1.856  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.014  -1.626  -3.215  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   13
CONECT    4    5   22
CONECT    5    6    6   12
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   27
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   28
CONECT   16   17   18   18
CONECT   17   29
CONECT   18   19   30
CONECT   19   20   21   21
CONECT   20   31
END

HMDB0034150
     RDKit          3D
Cernuine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0871   -0.4041   -1.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.0860   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916    0.5141    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.8500    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    0.6553    0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    1.1587   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    0.9159   -1.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032    0.1408   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.1033   -1.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996   -0.3807    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -1.1657    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -0.1305    1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    0.6796    1.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.2182    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0297    0.1575    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.3651    0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -0.4257    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -0.8446   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.7824   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999   -1.2469   -2.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722   -0.2552   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060    1.2907    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901    1.7953   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    1.3358   -2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    0.2994   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0470   -1.3229    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949   -0.5508    2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910    0.5352    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7253    0.3888   -0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0122   -1.2448   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.6263   -3.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  1  0
 10 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,6-Dihydroxy-2-[(3,4-dihydroxyphenyl)methylene]-3(2H)-benzofuranone, 9ci	HMDB
Aureusidin	HMDB

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one

CAS Registry Number

480-70-6

SMILES

OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4+

InChI Key

WBEFUVAYFSOUEA-YIXHJXPBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzofuran
Coumaran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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: HMDB0034150)

Cellular substructure

Membrane (HMDB: HMDB0034150)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034150)

Source

Exogenous

Food

Food (HMDB: HMDB0034150)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0034150)

Process

Not Available

Role

Biological role

pigment (HMDB: HMDB0034150)
biological pigment (HMDB: HMDB0034150)

Modulator

Inhibitor

Enzyme inhibitor

iodothyronine-deiodinase inhibitor (HMDB: HMDB0034150)

Nutrient

Nutrient (HMDB: HMDB0034150)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	295 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.64	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.97 m³·mol⁻¹	ChemAxon
Polarizability	28.03 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
DeepCCS	[M+H]+	168.163	30932474
DeepCCS	[M-H]-	165.805	30932474
DeepCCS	[M-2H]-	199.72	30932474
DeepCCS	[M+Na]+	174.947	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	169.0	32859911
AllCCS	[M+Na]+	170.0	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cernuine	OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1	5165.1	Standard polar	33892256
Cernuine	OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1	3089.4	Standard non polar	33892256
Cernuine	OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1	3038.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cernuine,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O)=C3)OC2=C1	3030.3	Semi standard non polar	33892256
Cernuine,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)/C(=C\C1=CC=C(O)C(O)=C1)O2	3012.4	Semi standard non polar	33892256
Cernuine,1TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)=CC=C1O	3012.9	Semi standard non polar	33892256
Cernuine,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O	3028.9	Semi standard non polar	33892256
Cernuine,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	2964.9	Semi standard non polar	33892256
Cernuine,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3081.6	Semi standard non polar	33892256
Cernuine,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3075.1	Semi standard non polar	33892256
Cernuine,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3010.3	Semi standard non polar	33892256
Cernuine,2TMS,isomer #5	C[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O	2990.6	Semi standard non polar	33892256
Cernuine,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	2979.4	Semi standard non polar	33892256
Cernuine,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	3051.0	Semi standard non polar	33892256
Cernuine,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	3021.7	Semi standard non polar	33892256
Cernuine,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3027.4	Semi standard non polar	33892256
Cernuine,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	2945.0	Semi standard non polar	33892256
Cernuine,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	3029.8	Semi standard non polar	33892256
Cernuine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O)=C3)OC2=C1	3291.3	Semi standard non polar	33892256
Cernuine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)/C(=C\C1=CC=C(O)C(O)=C1)O2	3292.4	Semi standard non polar	33892256
Cernuine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)=CC=C1O	3285.3	Semi standard non polar	33892256
Cernuine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O	3296.2	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3498.2	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3561.4	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3561.4	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3542.9	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O	3527.6	Semi standard non polar	33892256
Cernuine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3491.2	Semi standard non polar	33892256
Cernuine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3825.8	Semi standard non polar	33892256
Cernuine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3814.7	Semi standard non polar	33892256
Cernuine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3759.0	Semi standard non polar	33892256
Cernuine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3726.0	Semi standard non polar	33892256
Cernuine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	4022.2	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 - Cernuine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-0590000000-60fdd1319931a92de30e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cernuine GC-MS (4 TMS) - 70eV, Positive	splash10-0nt9-3340190000-3606f26744a113b986b8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cernuine 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 - Cernuine 10V, Positive-QTOF	splash10-000i-0190000000-3224cb2e84a595e2b340	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 20V, Positive-QTOF	splash10-0udr-0890000000-c05de1376c18f593bf58	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 40V, Positive-QTOF	splash10-0k9i-3910000000-e8808b7a3e9006b5469c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 10V, Negative-QTOF	splash10-000i-0090000000-fdb1d3719d99503795db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 20V, Negative-QTOF	splash10-000i-0190000000-610762391e234975806c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 40V, Negative-QTOF	splash10-014u-4980000000-43383fa8b2882e1be447	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 10V, Negative-QTOF	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 20V, Negative-QTOF	splash10-000i-0190000000-f58ff6de88c9e453912e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 40V, Negative-QTOF	splash10-0uxr-1290000000-99b520f618454ff3673c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 10V, Positive-QTOF	splash10-000i-0090000000-ad6070afb384abda8f3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 20V, Positive-QTOF	splash10-000i-0490000000-67faeaa5bc025bc62ebb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cernuine 40V, Positive-QTOF	splash10-016r-2390000000-5c2e59ba741b86d4337b	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

FDB012432

KNApSAcK ID

C00008027

Chemspider ID

11284214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6123196

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cernuine (HMDB0034150)

MOL for HMDB0034150 (Cernuine)

3D MOL for HMDB0034150 (Cernuine)

3D SDF for HMDB0034150 (Cernuine)

3D-SDF for HMDB0034150 (Cernuine)

PDB for HMDB0034150 (Cernuine)

3D PDB for HMDB0034150 (Cernuine)

SMILES for HMDB0034150 (Cernuine)

INCHI for HMDB0034150 (Cernuine)

Structure for HMDB0034150 (Cernuine)

3D Structure for HMDB0034150 (Cernuine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra