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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:40 UTC

Update Date

2022-03-07 02:52:14 UTC

HMDB ID

HMDB0029631

Secondary Accession Numbers

HMDB29631

Metabolite Identification

Common Name

Chalconaringenin

Description

Chalconaringenin, also known as isosalipurpol or naringenin chalcone, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, chalconaringenin is considered to be a flavonoid. Chalconaringenin has been detected, but not quantified in, several different foods, such as yautia (Xanthosoma sagittifolium), welsh onions (Allium fistulosum), dandelions (Taraxacum officinale), nectarines (Prunus persica var. nucipersica), and common chokecherries (Prunus virginiana). This could make chalconaringenin a potential biomarker for the consumption of these foods. Chalconaringenin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Chalconaringenin.

Structure

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

HMDB0029631
     RDKit          3D
Chalconaringenin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9801   -2.0749   -1.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -0.9394   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.3684   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711   -1.0037   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -0.4464   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.7520    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    1.2173    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2405    0.4786    0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5003    0.9296    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -0.7378   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.1679   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -0.3588   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.8436    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    1.6181    0.7830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.3734    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798    0.6511    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1608    1.1410    0.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7286   -0.5793   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -1.0387   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -2.2612   -1.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    0.5760    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.9827   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.3714    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1984    2.1566    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473    0.7135    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.3361   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -2.1301   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    2.5037    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9151    2.3158    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5257    1.7256   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6039   -1.1175   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0476   -2.8244   -1.6866 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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 20 32  1  0
M  END


  Mrv1652309042000372D          

 20 21  0  0  0  0            999 V2000
   -1.5319    1.3860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2464    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609    1.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609   -0.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609   -1.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898    1.3860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2464    0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -0.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -1.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030    1.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    1.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030    2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    2.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029631

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+

> <INCHI_KEY>
YQHMWTPYORBCMF-ZZXKWVIFSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.36744536621589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
3.9760640223333334

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.181889484974233

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.993338146782977

> <JCHEM_PKA_STRONGEST_BASIC>
-6.32703165501334

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
74.8006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naringenin chalcone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029631
     RDKit          3D
Chalconaringenin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9801   -2.0749   -1.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -0.9394   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.3684   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711   -1.0037   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -0.4464   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.7520    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    1.2173    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2405    0.4786    0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5003    0.9296    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -0.7378   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.1679   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -0.3588   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.8436    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    1.6181    0.7830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.3734    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798    0.6511    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1608    1.1410    0.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7286   -0.5793   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -1.0387   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -2.2612   -1.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    0.5760    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.9827   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.3714    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1984    2.1566    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473    0.7135    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.3361   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -2.1301   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    2.5037    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9151    2.3158    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5257    1.7256   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6039   -1.1175   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0476   -2.8244   -1.6866 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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      -2.860   2.587   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.193   1.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.527   2.587   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.861   1.817   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.861   0.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.527  -0.493   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.527  -2.033   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.194   2.587   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.193   0.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.860  -0.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.526   0.277   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.860  -2.033   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.526   1.817   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.192   2.587   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.141   1.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.475   2.587   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.192   4.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.141   4.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.475   4.127   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.809   4.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    2    6   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   19                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   16   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0029631
HETATM    1  O1  UNL     1      -0.980  -2.075  -1.101  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.039  -0.939  -0.516  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.236  -0.368  -0.138  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.371  -1.004  -0.395  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.657  -0.446  -0.023  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.834   0.752   0.610  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.119   1.217   0.934  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.240   0.479   0.622  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.500   0.930   0.937  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.088  -0.738  -0.018  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.826  -1.168  -0.322  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.310  -0.359  -0.296  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.508   0.844   0.314  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.463   1.618   0.783  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.797   1.373   0.506  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.880   0.651   0.062  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.161   1.141   0.234  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.729  -0.579  -0.566  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.457  -1.039  -0.723  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.295  -2.261  -1.346  1.00  0.00           O  
HETATM   21  H1  UNL     1       0.354   0.576   0.359  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.315  -1.983  -0.906  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.971   1.371   0.876  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.198   2.157   1.426  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.947   0.714   1.820  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.970  -1.336  -0.272  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.673  -2.130  -0.831  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.588   2.504   1.234  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.915   2.316   0.987  1.00  0.00           H  
HETATM   30  H10 UNL     1      -6.526   1.726  -0.530  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.604  -1.117  -0.901  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.048  -2.824  -1.687  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   11
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   11   26
CONECT   11   27
CONECT   12   13   13   19
CONECT   13   14   15
CONECT   14   28
CONECT   15   16   16   29
CONECT   16   17   18
CONECT   17   30
CONECT   18   19   19   31
CONECT   19   20
CONECT   20   32
END

HMDB0029631
     RDKit          3D
Chalconaringenin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9801   -2.0749   -1.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0390   -0.9394   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -0.3684   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3711   -1.0037   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -0.4464   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.7520    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187    1.2173    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2405    0.4786    0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5003    0.9296    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -0.7378   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.1679   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -0.3588   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    0.8436    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    1.6181    0.7830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.3734    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798    0.6511    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1608    1.1410    0.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7286   -0.5793   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4568   -1.0387   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -2.2612   -1.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    0.5760    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.9827   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.3714    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1984    2.1566    1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473    0.7135    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.3361   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -2.1301   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    2.5037    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9151    2.3158    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5257    1.7256   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6039   -1.1175   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0476   -2.8244   -1.6866 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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',6',4-Tetrahydroxychalcone	ChEBI
2'4'6'4-Tetrahydroxychalcone	ChEBI
Isosalipurpol	ChEBI
Naringenin chalcone	ChEBI
2',4,4',6'-Tetrahydroxychalcone	Kegg
Naringenin chalcone, (e)-isomer	MeSH
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

Traditional Name

naringenin chalcone

CAS Registry Number

5071-40-9

SMILES

OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+

InChI Key

YQHMWTPYORBCMF-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyphenol (CHEBI:15413 )
chalcones (CHEBI:15413 )
chalcones (C06561 )
Chalcones and dihydrochalcones (C06561 )
Chalcones and dihydrochalcones (LMPK12120264 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	184 °C	Not Available
Boiling Point	358.00 to 359.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	104.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.826 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.076 g/L	ALOGPS
logP	2.66	ALOGPS
logP	3.98	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.8 m³·mol⁻¹	ChemAxon
Polarizability	27.37 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
DeepCCS	[M+H]+	166.272	30932474
DeepCCS	[M-H]-	163.914	30932474
DeepCCS	[M-2H]-	196.863	30932474
DeepCCS	[M+Na]+	172.365	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.71 minutes	32390414
Predicted by Siyang on May 30, 2022	11.952 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2084.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	632.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	505.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1016.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	429.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1316.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	476.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	135.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chalconaringenin	OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1	4998.7	Standard polar	33892256
Chalconaringenin	OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1	2945.1	Standard non polar	33892256
Chalconaringenin	OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1	3137.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chalconaringenin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O)C=C2O)C=C1	2949.5	Semi standard non polar	33892256
Chalconaringenin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	2942.6	Semi standard non polar	33892256
Chalconaringenin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1	2964.3	Semi standard non polar	33892256
Chalconaringenin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C)C=C1	2855.8	Semi standard non polar	33892256
Chalconaringenin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O)C=C1	2871.1	Semi standard non polar	33892256
Chalconaringenin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1	2881.7	Semi standard non polar	33892256
Chalconaringenin,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	2907.4	Semi standard non polar	33892256
Chalconaringenin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O[Si](C)(C)C)C=C(O)C=C2O[Si](C)(C)C)C=C1	2851.4	Semi standard non polar	33892256
Chalconaringenin,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C1	2833.3	Semi standard non polar	33892256
Chalconaringenin,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1	2853.6	Semi standard non polar	33892256
Chalconaringenin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C1	2897.5	Semi standard non polar	33892256
Chalconaringenin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O)C=C2O)C=C1	3252.9	Semi standard non polar	33892256
Chalconaringenin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3257.1	Semi standard non polar	33892256
Chalconaringenin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1	3274.9	Semi standard non polar	33892256
Chalconaringenin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3452.4	Semi standard non polar	33892256
Chalconaringenin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C=C1	3482.4	Semi standard non polar	33892256
Chalconaringenin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1	3428.2	Semi standard non polar	33892256
Chalconaringenin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3470.9	Semi standard non polar	33892256
Chalconaringenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3682.4	Semi standard non polar	33892256
Chalconaringenin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3688.7	Semi standard non polar	33892256
Chalconaringenin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1	3632.2	Semi standard non polar	33892256
Chalconaringenin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3932.2	Semi standard non polar	33892256

Spectra

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Naringenin chalcone

METLIN ID

Not Available

PubChem Compound

5280960

PDB ID

Not Available

ChEBI ID

15413

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1416941

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. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Chalconaringenin → 3,4,5-trihydroxy-6-{4-[(1E)-3-oxo-3-(2,4,6-trihydroxyphenyl)prop-1-en-1-yl]phenoxy}oxane-2-carboxylic acid	details
Chalconaringenin → 6-{3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Chalconaringenin → {4-[(1E)-3-oxo-3-(2,4,6-trihydroxyphenyl)prop-1-en-1-yl]phenyl}oxidanesulfonic acid	details

Showing metabocard for Chalconaringenin (HMDB0029631)

MOL for HMDB0029631 (Chalconaringenin)

3D MOL for HMDB0029631 (Chalconaringenin)

3D SDF for HMDB0029631 (Chalconaringenin)

3D-SDF for HMDB0029631 (Chalconaringenin)

PDB for HMDB0029631 (Chalconaringenin)

3D PDB for HMDB0029631 (Chalconaringenin)

SMILES for HMDB0029631 (Chalconaringenin)

INCHI for HMDB0029631 (Chalconaringenin)

Structure for HMDB0029631 (Chalconaringenin)

3D Structure for HMDB0029631 (Chalconaringenin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions