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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

Detected and Quantified

Creation Date

2006-05-22 15:12:02 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002670

Secondary Accession Numbers

HMDB02670

Metabolite Identification

Common Name

Naringenin

Description

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4', 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. Naringenin is a biomarker for the consumption of citrus fruits.

Structure

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

HMDB0002670
     RDKit          3D
Naringenin
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.6298   -2.9086   -1.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -1.8094   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -1.5923   -0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.0936   -0.3236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9313    0.1730   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003    0.5817   -1.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1303    0.8398   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.6782    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    0.9267    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7913    0.2719    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602    0.0243    1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423    0.4761    0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112    0.3396    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.2813    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    1.1107    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214    2.0183    1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -0.0553    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530   -1.0217   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -2.1865   -0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848   -0.8166   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.1905    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6590   -1.8583   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622    0.3532   -1.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283    0.7093   -2.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7570    1.1572   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5951    1.2254    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2287    0.1641    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.2957    2.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    2.1880    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    2.8865    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -0.2226    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610   -2.3542   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END


  Mrv1652309272007432D          

 20 22  0  0  0  0            999 V2000
 9999.6614 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.232010001.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.807810000.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.236710000.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5222 9999.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2366 9998.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.803210001.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088510000.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8030 9999.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710000.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662310000.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9999.7759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  6  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
  1 18  2  0  0  0  0
 16  5  2  0  0  0  0
  8 17  2  0  0  0  0
 20 12  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002670

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

> <INCHI_KEY>
FTVWIRXFELQLPI-ZDUSSCGKSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.31257446768327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.835108050333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.199181425928916

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.856155974915031

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950228081125502

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naringenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002670
     RDKit          3D
Naringenin
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.6298   -2.9086   -1.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -1.8094   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -1.5923   -0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.0936   -0.3236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9313    0.1730   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003    0.5817   -1.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1303    0.8398   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.6782    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    0.9267    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7913    0.2719    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602    0.0243    1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423    0.4761    0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112    0.3396    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.2813    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    1.1107    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214    2.0183    1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -0.0553    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530   -1.0217   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -2.1865   -0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848   -0.8166   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.1905    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6590   -1.8583   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622    0.3532   -1.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283    0.7093   -2.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7570    1.1572   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5951    1.2254    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2287    0.1641    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.2957    2.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    2.1880    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    2.8865    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -0.2226    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610   -2.3542   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0358662.387   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8672.7008669.332   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8663.3758662.387   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8660.7088667.026   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8663.3758667.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0418666.248   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.0418664.708   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.3758663.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.3668668.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.0338669.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.6998668.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.6998667.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.0328666.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.3668667.025   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8666.0368667.018   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8664.7038666.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.7038664.708   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0368663.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.3708664.708   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3708666.248   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2    9                                                            
CONECT    3    8                                                            
CONECT    4    6                                                            
CONECT    5    6   16                                                       
CONECT    6    5    7    4                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3   17                                                  
CONECT    9   10   14    2                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   17   15    5                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   19    1                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   12                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0002670
HETATM    1  O1  UNL     1       1.630  -2.909  -1.001  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.211  -1.809  -0.535  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.244  -1.592  -0.481  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.509  -0.094  -0.324  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.931   0.173  -0.050  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.800   0.582  -1.043  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.130   0.840  -0.828  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.615   0.678   0.457  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.960   0.927   0.734  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.791   0.272   1.489  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.460   0.024   1.223  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.342   0.476   0.656  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.711   0.340   0.526  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.615   1.281   0.961  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.973   1.111   0.814  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.921   2.018   1.230  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.400  -0.055   0.207  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.553  -1.022  -0.242  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.970  -2.186  -0.848  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.185  -0.817  -0.078  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.770  -2.190   0.266  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.659  -1.858  -1.496  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.262   0.353  -1.309  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.428   0.709  -2.048  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.757   1.157  -1.652  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.595   1.225   0.008  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.229   0.164   2.470  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.807  -0.296   2.031  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.271   2.188   1.433  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.739   2.887   1.676  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.467  -0.223   0.076  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.961  -2.354  -0.977  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   12   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   29
CONECT   15   16   17   17
CONECT   16   30
CONECT   17   18   31
CONECT   18   19   20   20
CONECT   19   32
END

HMDB0002670
     RDKit          3D
Naringenin
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.6298   -2.9086   -1.0011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -1.8094   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -1.5923   -0.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5092   -0.0936   -0.3236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9313    0.1730   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003    0.5817   -1.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1303    0.8398   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.6782    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    0.9267    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7913    0.2719    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602    0.0243    1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423    0.4761    0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112    0.3396    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.2813    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730    1.1107    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214    2.0183    1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -0.0553    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530   -1.0217   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -2.1865   -0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848   -0.8166   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.1905    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6590   -1.8583   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622    0.3532   -1.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283    0.7093   -2.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7570    1.1572   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5951    1.2254    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2287    0.1641    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.2957    2.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    2.1880    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    2.8865    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -0.2226    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610   -2.3542   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(2S)-Naringenin	ChEBI
(2S)-Naringenin	ChEBI
(S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
4',5,7-Trihydroxyflavanone	ChEBI
Naringetol	ChEBI
Pelargidanon	ChEBI
Salipurpol	ChEBI
(-)-Naringenin	HMDB
Asahina	HMDB
Naringenine	HMDB
Salipurol	HMDB
(2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
(2S)-4',5,7-Trihydroxyflavanone	PhytoBank
(2S)-4’,5,7-Trihydroxyflavanone	PhytoBank
(S)-Naringenin	PhytoBank
S-Dihydrogenistein	PhytoBank
5,7,4'-Trihydroxyflavanone	PhytoBank
5,7,4’-Trihydroxyflavanone	PhytoBank

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

naringenin

CAS Registry Number

480-41-1

SMILES

OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naringenin (CHEBI:17846 )
flavanones (C00509 )
Flavanones (LMPK12140001 )

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cell membrane (HMDB: HMDB0002670)

Biofluid or Excreta

Cell

Fibroblast

Fibroblast (HMDB: HMDB0002670)

Fibroblasts (HMDB: HMDB0002670)

Organ

Liver (HMDB: HMDB0002670)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12421849)

Excreta

Biofluid or Excreta

Urine (PMID: 16197573)
Feces (PMID: 20809621)

Cellular substructure

Membrane (HMDB: HMDB0002670)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002670)

Source

Exogenous

Food

Food (HMDB: HMDB0002670)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)
Tomato (HMDB: HMDB0002670)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (HMDB: HMDB0002670)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Bilberry (FooDB: FOOD00193)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Ground meat

Sausage (FooDB: FOOD00652)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0002670)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavonoid Biosynthesis (PathBank: SMP0012021)

Role

Biological role

Modulator

anti aflatoxin (HMDB: HMDB0002670)
anti aggregant (HMDB: HMDB0002670)
anti Alzheimeran (HMDB: HMDB0002670)
anti amnesic (HMDB: HMDB0002670)
anti amyloid-beta (HMDB: HMDB0002670)
anti bacterial (HMDB: HMDB0002670)
anti cancer (HMDB: HMDB0002670)
anti escherichic (HMDB: HMDB0002670)
anti estrogenic (HMDB: HMDB0002670)
anti fibrotic (HMDB: HMDB0002670)
anti hepatotoxic (HMDB: HMDB0002670)
anti herpetic (HMDB: HMDB0002670)
anti HIV (HMDB: HMDB0002670)
anti inflammatory (HMDB: HMDB0002670)
anti leukemic (HMDB: HMDB0002670)
anti mutagenic (HMDB: HMDB0002670)
Antioxidant (HMDB: HMDB0002670)
anti peristaltic (HMDB: HMDB0002670)
anti peroxidative (HMDB: HMDB0002670)
anti radicular (HMDB: HMDB0002670)
anti sindhis (HMDB: HMDB0002670)
anti spasmodic (HMDB: HMDB0002670)
anti staphylococcic (HMDB: HMDB0002670)
antitumor (HMDB: HMDB0002670)
antitumor promoter (HMDB: HMDB0002670)
anti ulcer (HMDB: HMDB0002670)
antiviral agent (HMDB: HMDB0002670)
aphidifuge (HMDB: HMDB0002670)
cancer preventive (HMDB: HMDB0002670)
candidicide (HMDB: HMDB0002670)
choleretic (HMDB: HMDB0002670)
embryotoxic (HMDB: HMDB0002670)
estrogenic (HMDB: HMDB0002670)
fungicide (HMDB: HMDB0002670)
fungistat (HMDB: HMDB0002670)
hepatoprotective (HMDB: HMDB0002670)
serotonergic antagonist (HMDB: HMDB0002670)
teratogenic agent (HMDB: HMDB0002670)
utero trophic (HMDB: HMDB0002670)
Pro-oxidant (HMDB: HMDB0002670)

Indirect biological role

antioxidant (HMDB: HMDB0002670)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antiviral agent (HMDB: HMDB0002670)
fungicide (HMDB: HMDB0002670)
neuroprotective agent (HMDB: HMDB0002670)
serotonergic antagonist (HMDB: HMDB0002670)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0002670)

Pharmaceutical industry

Anti-allergic (HMDB: HMDB0002670)

Biomarker

Fruits Consumption (MarkerDB: MDB00000396)
Vegetables Consumption (MarkerDB: MDB00000396)
Fruits + Vegetables Consumption (MarkerDB: MDB00000396)
Fruit Juices Consumption (MarkerDB: MDB00000396)
Citrus Fruits Consumption (MarkerDB: MDB00000396)
Grapefruit Consumption (MarkerDB: MDB00000396)
Grapefruit Juice Consumption (MarkerDB: MDB00000396)
Orange Consumption (MarkerDB: MDB00000396)
Orange Juice Consumption (MarkerDB: MDB00000396)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	251 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.52	PERRISSOUD,D & TESTA,B (1986)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	167.328	30932474
[M+H]+	Baker	167.965	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.31 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
DarkChem	[M+H]+	163.881	31661259
DarkChem	[M-H]-	164.153	31661259
DeepCCS	[M+H]+	163.691	30932474
DeepCCS	[M-H]-	161.333	30932474
DeepCCS	[M-2H]-	194.54	30932474
DeepCCS	[M+Na]+	169.784	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naringenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O	3915.8	Standard polar	33892256
Naringenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O	2952.4	Standard non polar	33892256
Naringenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O	2843.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naringenin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	2812.2	Semi standard non polar	33892256
Naringenin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	2777.2	Semi standard non polar	33892256
Naringenin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	2792.7	Semi standard non polar	33892256
Naringenin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1	2786.0	Semi standard non polar	33892256
Naringenin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	2847.9	Semi standard non polar	33892256
Naringenin,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2746.9	Semi standard non polar	33892256
Naringenin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	2821.6	Semi standard non polar	33892256
Naringenin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3094.8	Semi standard non polar	33892256
Naringenin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	3057.8	Semi standard non polar	33892256
Naringenin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	3052.9	Semi standard non polar	33892256
Naringenin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3298.3	Semi standard non polar	33892256
Naringenin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3330.6	Semi standard non polar	33892256
Naringenin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3268.5	Semi standard non polar	33892256
Naringenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3502.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4r-2961300000-725a9d843a4286e86b06	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)	splash10-0a4r-2961300000-725a9d843a4286e86b06	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)	splash10-00fs-1951400000-44c9c035aeffcacf4e8c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)	splash10-004l-1931100000-ec4d00bbd2895d4d5f9c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)	splash10-0a4r-2961300000-6cd5d798a9dad326f771	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1290000000-3182db290eb43c661919	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-2531900000-0583af94457df8aad759	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-00di-0190000000-ba73aef4d7cf20a2777d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-066r-3900000000-98ba56d82461a2dc7f6f	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-02t9-9600000000-005d5eb55c1f6f3b893d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-00di-0090000000-87dba9fe511299bf27e8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-00di-0090000000-52282430f89f3cfd51ff	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0g4i-1960000000-74e384d175dd4f05938c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-1900000000-702ce5f0315e56bb08a0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0udi-2900000000-aeb81b324d8162537df3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0fk9-1960000000-b4a541e5476f88624522	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOF	splash10-000i-0090000000-cfa015b97699d9b8d3a9	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 25V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 40V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 10V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 30V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 20V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOF	splash10-00di-0090000000-dae76236c5699dabc079	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF 25V, Negative-QTOF	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOF	splash10-00di-0090010000-5e9a02398f13b71eccfb	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 10V, Positive-QTOF	splash10-00di-0290000000-32844ab19a143b70951b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 20V, Positive-QTOF	splash10-0fk9-0980000000-93073e4c39e23c3099c5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 40V, Positive-QTOF	splash10-0uki-4900000000-8d2daa4eb7a40b866718	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 10V, Negative-QTOF	splash10-00di-0090000000-b29e35ecf9be0aa440c2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 20V, Negative-QTOF	splash10-00di-1390000000-e9112df7c7b29664a011	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 40V, Negative-QTOF	splash10-014l-6920000000-3b7e4e282dc4008e8c8e	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00815 +/- 0.0154 uM	Adult (>18 years old)	Female	Normal	12395214	details
Blood	Detected and Quantified	0.02 +/- 0.05 uM	Adult (>18 years old)	Both	Normal	12421849	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	20100371	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	16197573	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	20441150	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	21820093	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	18710603	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	10637051	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	15969493	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	15309458	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0171 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.0176 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.0514 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.0542 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Detected and Quantified	0.0553 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.137 +/- 0.0979 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17538531	details
Urine	Detected and Quantified	0.560 +/- 1.330 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.660 +/- 1.593 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	20100371	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	20441150	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	21820093	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	18710603	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	10637051	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	15969493	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 201	15309458	details
Urine	Detected and Quantified	0.273 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.373 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.0065 +/- 0.013 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.032 +/- 0.032 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.019 +/- 0.013 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.019 +/- 0.026 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.0 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	1.62 +/- 0.82 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.55 +/- 0.20 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.109 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.234 +/- 0.368 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB03467

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Naringenin

METLIN ID

3401

PubChem Compound

439246

PDB ID

Not Available

ChEBI ID

17846

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000396

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG: Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther. 1992 Jun;261(3):1195-9. [PubMed:1602384 ]
Walker D, Flinois JP, Monkman SC, Beloc C, Boddy AV, Cholerton S, Daly AK, Lind MJ, Pearson AD, Beaune PH, et al.: Identification of the major human hepatic cytochrome P450 involved in activation and N-dechloroethylation of ifosfamide. Biochem Pharmacol. 1994 Mar 29;47(7):1157-63. [PubMed:8161344 ]
Ameer B, Weintraub RA, Johnson JV, Yost RA, Rouseff RL: Flavanone absorption after naringin, hesperidin, and citrus administration. Clin Pharmacol Ther. 1996 Jul;60(1):34-40. [PubMed:8689809 ]
Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Mar 5;801(2):363-7. [PubMed:14751808 ]
Guengerich FP, Kim DH: In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis. 1990 Dec;11(12):2275-9. [PubMed:2265479 ]
Ishii K, Furuta T, Kasuya Y: Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Aug 30;683(2):225-9. [PubMed:8891919 ]
Matsuo M, Sasaki N, Saga K, Kaneko T: Cytotoxicity of flavonoids toward cultured normal human cells. Biol Pharm Bull. 2005 Feb;28(2):253-9. [PubMed:15684479 ]
Franke AA, Cooney RV, Henning SM, Custer LJ: Bioavailability and antioxidant effects of orange juice components in humans. J Agric Food Chem. 2005 Jun 29;53(13):5170-8. [PubMed:15969493 ]
Fuhr U, Kummert AL: The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther. 1995 Oct;58(4):365-73. [PubMed:7586927 ]
Lin YT, Hsiu SL, Hou YC, Chen HY, Chao PD: Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. Biol Pharm Bull. 2003 May;26(5):747-51. [PubMed:12736527 ]
Malaveille C, Hautefeuille A, Pignatelli B, Talaska G, Vineis P, Bartsch H: Dietary phenolics as anti-mutagens and inhibitors of tobacco-related DNA adduction in the urothelium of smokers. Carcinogenesis. 1996 Oct;17(10):2193-200. [PubMed:8895488 ]

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

Naringenin → 6-{4-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Naringenin → 3,4,5-trihydroxy-6-{[(2S)-7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic acid	details
Naringenin → 3,4,5-trihydroxy-6-{[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-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

Naringenin → {4-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}oxidanesulfonic acid	details

Showing metabocard for Naringenin (HMDB0002670)

MOL for HMDB0002670 (Naringenin)

3D MOL for HMDB0002670 (Naringenin)

3D SDF for HMDB0002670 (Naringenin)

3D-SDF for HMDB0002670 (Naringenin)

PDB for HMDB0002670 (Naringenin)

3D PDB for HMDB0002670 (Naringenin)

SMILES for HMDB0002670 (Naringenin)

INCHI for HMDB0002670 (Naringenin)

Structure for HMDB0002670 (Naringenin)

3D Structure for HMDB0002670 (Naringenin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions