NP-MRD: Showing NP-Card for Naringenin (NP0001313)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:02 UTC

Updated at

2024-09-03 04:15:59 UTC

NP-MRD ID

NP0001313

Natural Product DOI

https://doi.org/10.57994/0482

Secondary Accession Numbers

None

Natural Product 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>
NP0001313

> <DATABASE_NAME>
NP-MRD

> <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

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	HMDB
(2S)-4',5,7-Trihydroxyflavanone	HMDB
(2S)-4’,5,7-trihydroxyflavanone	HMDB
(S)-Naringenin	HMDB
S-Dihydrogenistein	HMDB
5,7,4'-Trihydroxyflavanone	HMDB
5,7,4’-trihydroxyflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

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

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

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Acacia dealbata	KNApSAcK Database	22123792
Acacia longifolia	KNApSAcK Database	22123792
Acer pictum subsp. Mono	LOTUS Database	35616633
Achyrocline flaccida	LOTUS Database	35616633
Acritopappus confertus	LOTUS Database	35616633
Actinidia chinensis	FooDB	USDA
Adenothamnus validus	LOTUS Database	35616633
Aeonium lindleyi	LOTUS Database	35616633
Aeschynanthus bracteatus	KNApSAcK Database	22123792
Afzelia bipindensis	LOTUS Database	35616633
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Aglaia rubiginosa	LOTUS Database	35616633
Allagopappus viscosissimus	LOTUS Database	35616633
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	PHENOL EXPLORER
Allium cepa L.	FooDB	USDA
Allium fistulosum	FooDB	FooDB
Allium sativum	KNApSAcK Database	22123792
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Alpinia zerumbet	LOTUS Database	35616633
Amaranthus	FooDB	FooDB
Ambrosia bidentata	LOTUS Database	35616633
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	KNApSAcK Database	22123792
Ananas comosus	FooDB	USDA
Anastatica hierochuntica	LOTUS Database	35616633
Anethum graveolens	FooDB	PHENOL EXPLORER
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Antiphiona pinnatisecta	LOTUS Database	35616633
Antirrhinum majus	KNApSAcK Database	22123792
Apium graveolens	FooDB	USDA
Apium graveolens var. dulce	FooDB	PHENOL EXPLORER
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	PHENOL EXPLORER
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	USDA
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia argyi	LOTUS Database	35616633
Artemisia barrelieri	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Artemisia campestris ssp.maritima	KNApSAcK Database	22123792
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia glutinosa	KNApSAcK Database	22123792
Artemisia spp.	KNApSAcK Database	22123792
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	KNApSAcK Database	22123792
Aster koraiensis	LOTUS Database	35616633
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa	LOTUS Database	35616633
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis linearifolia	LOTUS Database	35616633
Baccharis spp.	KNApSAcK Database	22123792
Bahiopsis laciniata	LOTUS Database	35616633
Basella alba	FooDB	FooDB
Bauhinia guianensis	KNApSAcK Database	22123792
Benincasa hispida	FooDB	FooDB
Berchemia formosana	LOTUS Database	35616633
Berchemia racemosa	LOTUS Database	35616633
Bertholletia excelsa	FooDB	USDA
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Betula maximowicziana	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Borago officinalis	FooDB	FooDB
Bracteantha viscosa	LOTUS Database	35616633
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	KNApSAcK Database	22123792
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	PHENOL EXPLORER
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	PHENOL EXPLORER
Brassica oleracea var. sabauda	FooDB	PHENOL EXPLORER
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	USDA
Brosimum acutifolium	LOTUS Database	35616633
Brosimum alicastrum	FooDB	FooDB
Broussonetia papyrifera	KNApSAcK Database	22123792
Brucea javanica	LOTUS Database	35616633
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Camellia sinensis	LOTUS Database	35616633
Camellia sinensis var.assamica	KNApSAcK Database	22123792
Canarium ovatum	FooDB	FooDB
Cannabis indica	KNApSAcK Database	22123792
Cannabis inflorescences	KNApSAcK Database	22123792
Cannabis sativa	KNApSAcK Database	22123792
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capsicum annuum	KNApSAcK Database	22123792
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carapa guianensis	LOTUS Database	35616633
Carduus tenuiflorus	LOTUS Database	35616633
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	USDA
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Cedrus deodara	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea spp.	KNApSAcK Database	22123792
Ceratonia siliqua	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysothamnus humilis	KNApSAcK Database	22123792
Chrysothamnus viscidiflorus	KNApSAcK Database	22123792
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Cistus laurifolius	LOTUS Database	35616633
Citrullus lanatus	FooDB	USDA
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	USDA
Citrus aurantiifolia	FooDB	PHENOL EXPLORER
Citrus aurantium	LOTUS Database	35616633
Citrus aurantium L. var. amara	KNApSAcK Database	22123792
Citrus grandis	KNApSAcK Database	22123792
Citrus grandis var.tomentosa	KNApSAcK Database	22123792
Citrus latifolia	FooDB	USDA
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	FooDB	USDA
Citrus medica	LOTUS Database	35616633
Citrus paradisi	FooDB	PHENOL EXPLORER
Citrus reticulata	FooDB	USDA
Citrus sinensis	LOTUS Database	35616633
Citrus spp.	KNApSAcK Database	22123792
Citrus trifoliata	LOTUS Database	35616633
Citrus unshiu	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cochlospermum gillivraei	KNApSAcK Database	22123792
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Combretum imberbe	LOTUS Database	35616633
Commiphora wightii	LOTUS Database	35616633
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	PHENOL EXPLORER
Coriaria intermedia	LOTUS Database	35616633
Corylus	FooDB	USDA
Corylus avellana	FooDB	FooDB
Corymbia maculata	LOTUS Database	35616633
Cota palaestina	LOTUS Database	35616633
Cotoneaster orbicularis	LOTUS Database	35616633
Couepia paraensis	LOTUS Database	35616633
Craspedolobium schochii	LOTUS Database	35616633
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Crotalaria assamica	KNApSAcK Database	22123792
Crotalaria pallida	KNApSAcK Database	22123792
Cryptomeria japonica	LOTUS Database	35616633
Cucumis melo	FooDB	USDA
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cudrania cochinchinensis var. gerontogea	KNApSAcK Database	22123792
Cuminum cyminum	FooDB	PHENOL EXPLORER
Curcuma longa	FooDB	FooDB
Curcuma mangga	KNApSAcK Database	22123792
Cycas circinalis	LOTUS Database	35616633
Cyclopia intermedia	LOTUS Database	35616633
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	USDA
Dahlia spp.	KNApSAcK Database	22123792
Dalbergia odorifera	KNApSAcK Database	22123792
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia stevensonii	KNApSAcK Database	22123792
Daucus carota	KNApSAcK Database	22123792
Daucus carota ssp. sativus	FooDB	USDA
Deinandra minthornii	LOTUS Database	35616633
Dendrobium densiflorum	LOTUS Database	35616633
Dendrobium densiflorum Lindl.ex.Wall.	KNApSAcK Database	22123792
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea alata	KNApSAcK Database	22123792
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Diplostephium cinereum	LOTUS Database	35616633
Dracocephalum tanguticum	LOTUS Database	35616633
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Elaeodendron croceum	LOTUS Database	35616633
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Entada phaseoloides	LOTUS Database	35616633
Ephedra sinica	KNApSAcK Database	22123792
Equisetum arvense	LOTUS Database	35616633
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eriodictyon angustifolium	LOTUS Database	35616633
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Euchresta japonica	LOTUS Database	35616633
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Euphorbia helioscopia	Plant	KNApSAcK
Euscaphis konishii	KNApSAcK Database	22123792
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	USDA
Ficus nervosa	LOTUS Database	35616633
Ficus pumila	LOTUS Database	35616633
Flammulina velutipes	FooDB	FooDB
Flemingia philippinensis	LOTUS Database	35616633
Flemingia stricta	KNApSAcK Database	22123792
Foeniculum vulgare	FooDB	PHENOL EXPLORER
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Garcinia mangostana	FooDB	FooDB
Garcinia multiflora	KNApSAcK Database	22123792
Garcinia neglecta	KNApSAcK Database	22123792
Gaylussacia baccata	FooDB	FooDB
Gentiana lutea L. var. aurantiaca	KNApSAcK Database	22123792
Gentiana triflora	KNApSAcK Database	22123792
Ginkgo biloba	KNApSAcK Database	22123792
Glycine max	KNApSAcK Database	22123792
Glycyrrhiza echinata	LOTUS Database	35616633
Glycyrrhiza glabra	KNApSAcK Database	22123792
Glycyrrhiza uralensis	KNApSAcK Database	22123792
Gossypium	FooDB	FooDB
Goyazianthus tetrastichus	LOTUS Database	35616633
Grifola frondosa	FooDB	FooDB
Gynerium sagittatum	KNApSAcK Database	22123792
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Helichrysum arenarium	KNApSAcK Database	22123792
Helichrysum armenium	LOTUS Database	35616633
Helichrysum bracteatum (Vent.)Andr.	KNApSAcK Database	22123792
Helichrysum graveolen	KNApSAcK Database	22123792
Heliotropium chenopodiaceum	LOTUS Database	35616633
Heliotropium sclerocarpum	LOTUS Database	35616633
Heliotropium sinuatum	LOTUS Database	35616633
Heliotropium taltalense	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Hymenoclea monogyra	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	PHENOL EXPLORER
Illicium verum	FooDB	FooDB
Intsia bijuga	KNApSAcK Database	22123792
Inula salsoloides	LOTUS Database	35616633
Inulanthera calva	LOTUS Database	35616633
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	USDA
Juniperus chinensis	LOTUS Database	35616633
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	PHENOL EXPLORER
Lagenaria siceraria	FooDB	FooDB
Laguncularia racemosa	LOTUS Database	35616633
Lamyropsis cynaroides	LOTUS Database	35616633
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Leiocarpa semicalva	LOTUS Database	35616633
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Lespedeza cyrtobotrya	KNApSAcK Database	22123792
Levisticum officinale	FooDB	FooDB
Limonium aureum	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Linum usitatissimum	FooDB	FooDB
Lippia graveolens	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Litchi chinensis	FooDB	FooDB
Lonicera japonica	KNApSAcK Database	22123792
Lotus uliginosus	LOTUS Database	35616633
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Lupinus subcarnosus	KNApSAcK Database	22123792
Lupinus texensis	KNApSAcK Database	22123792
Lychnophora ericoides	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Macadamia	FooDB	USDA
Macadamia tetraphylla	FooDB	FooDB
Maclura cochinchinensis	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Maclura tinctoria	KNApSAcK Database	22123792
Maclura tricuspidata	LOTUS Database	35616633
Magnolia denudata	KNApSAcK Database	22123792
Magnolia liliiflora	KNApSAcK Database	22123792
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	PHENOL EXPLORER
Mammea americana	FooDB	FooDB
Mandevilla hirsuta	LOTUS Database	35616633
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria chamomilla	LOTUS Database	35616633
Matricaria recutita	FooDB	PHENOL EXPLORER
Matteuccia struthiopteris	FooDB	FooDB
Matthiola incana	LOTUS Database	35616633
Medicago arabica	KNApSAcK Database	22123792
Medicago sativa	KNApSAcK Database	22123792
Medicago truncatula	KNApSAcK Database	22123792
Melissa officinalis L.	FooDB	PHENOL EXPLORER
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	PHENOL EXPLORER
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Millettia brandisiana	KNApSAcK Database	22123792
Mimosa hostilis	KNApSAcK Database	22123792
Mimosa tenuiflora	LOTUS Database	35616633
Momordica charantia	KNApSAcK Database	22123792
Monopteryx inpae	LOTUS Database	35616633
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Musa acuminata	KNApSAcK Database	22123792
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Nymphaea caerulea	KNApSAcK Database	22123792
Ocimum basilicum	FooDB	PHENOL EXPLORER
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum dictamnus	LOTUS Database	35616633
Origanum majorana	FooDB	PHENOL EXPLORER
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	FooDB
Ormosia henryi	LOTUS Database	35616633
Ormosia monosperma	LOTUS Database	35616633
Oryza rufipogon	FooDB	FooDB
Oryza sativa	KNApSAcK Database	22123792
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Paulownia coreana	LOTUS Database	35616633
Paulownia tomentosa	LOTUS Database	35616633
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	USDA
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petunia hybrida	KNApSAcK Database	22123792
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Phlomis aurea	LOTUS Database	35616633
Phlomis caucasica	KNApSAcK Database	22123792
Phoenix dactylifera	FooDB	USDA
Photinia melanocarpa	FooDB	FooDB
Phyllanthus emblica	KNApSAcK Database	22123792
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Picea jezoensis	LOTUS Database	35616633
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	PHENOL EXPLORER
Pinus	FooDB	FooDB
Pinus edulis	FooDB	USDA
Pinus sibirica	KNApSAcK Database	22123792
Piper crassinervium	LOTUS Database	35616633
Piper crassinervium Kunth	KNApSAcK Database	22123792
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	PHENOL EXPLORER
Pisum sativum	FooDB	FooDB
Pittocaulon praecox	LOTUS Database	35616633
Pittocaulon velatum	LOTUS Database	35616633
Plazia daphnoides	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	FooDB
Podocarpus fasciculus	KNApSAcK Database	22123792
Polygonum alpinum	FooDB	FooDB
Polygonum minus	KNApSAcK Database	22123792
Polymnia fruticosa	KNApSAcK Database	22123792
Populus balsamifera	LOTUS Database	35616633
Populus davidiana	LOTUS Database	35616633
Populus deltoides	LOTUS Database	35616633
Populus szechuanica	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Premna fulva	LOTUS Database	35616633
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	KNApSAcK Database	22123792
Prunus avium L.	FooDB	USDA
Prunus campanulata	LOTUS Database	35616633
Prunus cerasus	KNApSAcK Database	22123792
Prunus cornuta	LOTUS Database	35616633
Prunus davidiana	KNApSAcK Database	22123792
Prunus domestica	FooDB	PHENOL EXPLORER
Prunus dulcis	FooDB	PHENOL EXPLORER
Prunus mume	KNApSAcK Database	22123792
Prunus persica	KNApSAcK Database	22123792
Prunus persica var. nucipersica	FooDB	USDA
Prunus persica var. persica	FooDB	FooDB
Prunus serrulata	LOTUS Database	35616633
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Prunus yedoensis	KNApSAcK Database	22123792
Pseudotsuga wilsoniana	KNApSAcK Database	22123792
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Pterocarpus marsupium	KNApSAcK Database	22123792
Punica granatum	FooDB	FooDB
Punica granatum L.	KNApSAcK Database	22123792
Pyracantha coccinea	LOTUS Database	35616633
Pyrus communis	FooDB	USDA
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	KNApSAcK Database	22123792
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Retama raetam	LOTUS Database	35616633
Rheum rhabarbarum	FooDB	FooDB
Rhynchosia beddomei	KNApSAcK Database	22123792
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	PHENOL EXPLORER
Ribes rubrum	FooDB	PHENOL EXPLORER
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	PHENOL EXPLORER
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix caprea	LOTUS Database	35616633
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia mexicana	LOTUS Database	35616633
Salvia officinalis	FooDB	PHENOL EXPLORER
Salvia rosmarinus	FooDB	PHENOL EXPLORER
Salvia xalapensis	LOTUS Database	35616633
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Sarcophyte sanguinea	LOTUS Database	35616633
Satureja cuneifolia	LOTUS Database	35616633
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Satureja subspicata	KNApSAcK Database	22123792
Scalesia baurii	LOTUS Database	35616633
Scorzonera hispanica	FooDB	FooDB
Scutellaria strigillosa	LOTUS Database	35616633
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Senna tora	LOTUS Database	35616633
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Shuteria involucrata	LOTUS Database	35616633
Sinapis alba	FooDB	FooDB
Sinningia cardinalis	LOTUS Database	35616633
Sisymbrium	FooDB	FooDB
Smallanthus fruticosus	LOTUS Database	35616633
Smilax bracteata	Plant	KNApSAcK
Smilax corbularia	LOTUS Database	35616633
Smilax excelsa	LOTUS Database	35616633
Smilax perfoliata	LOTUS Database	35616633
Solanum lycopersicum	FooDB	USDA
Solanum lycopersicum var. cerasiforme	FooDB	PHENOL EXPLORER
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	USDA
Sophora flavescens	KNApSAcK Database	22123792
Sophora japonica	KNApSAcK Database	22123792
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	USDA
Spinacia oleracea	FooDB	FooDB
Stachys aegyptiaca	LOTUS Database	35616633
Steiractinia sodiroi	LOTUS Database	35616633
Streptomyces graminofaciens	LOTUS Database	35616633
Swartzia polyphylla	KNApSAcK Database	22123792
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Taxus chinensis	KNApSAcK Database	22123792
Taxus fuana	KNApSAcK Database	22123792
Taxus wallichiana	LOTUS Database	35616633
Taxus yunnanensis	KNApSAcK Database	22123792
Tetragonia tetragonioides	FooDB	FooDB
Teucrium chamaedrys	LOTUS Database	35616633
Thelesperma	FooDB	FooDB
Theobroma cacao L.	KNApSAcK Database	22123792
Thymus herba-barona	LOTUS Database	35616633
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	KNApSAcK Database	22123792
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Typha angustifolia	KNApSAcK Database	22123792
Urospermum dalechampii	LOTUS Database	35616633
Vaccinium	FooDB	USDA
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	USDA
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	PHENOL EXPLORER
Vachellia nilotica	LOTUS Database	35616633
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum cotinifolium	LOTUS Database	35616633
Viburnum edule	FooDB	FooDB
Vicia faba	KNApSAcK Database	22123792
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Viscum angulatum	KNApSAcK Database	22123792
Viscum coloratum	KNApSAcK Database	22123792
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	PHENOL EXPLORER
Wyethia angustifolia	LOTUS Database	35616633
Xanthoceras sorbifolia	KNApSAcK Database	22123792
Xanthoceras sorbifolium	LOTUS Database	35616633
Xanthorrhoea fulva	LOTUS Database	35616633
Xanthosoma sagittifolium	FooDB	FooDB
Xerochrysum bracteatum	LOTUS Database	35616633
Xylopia poilanei	KNApSAcK Database	22123792
Zea mays	KNApSAcK Database	22123792
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	251 °C	Not Available
Boiling Point	577.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	475.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.52	Perrissoud, D., & Testa, B. (1986). Inhibiting or potentiating effects of flavonoids on carbon tetrachloride-induced toxicity in isolated rat hepatocytes. Arzneimittel-forschung, 36(8), 1249-1253.

Predicted 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

External Links

HMDB ID

HMDB0002670

DrugBank ID

DB03467

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

rw1193531

References

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 ]
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 ]

Showing NP-Card for Naringenin (NP0001313)

MOL for NP0001313 (Naringenin)

3D MOL for NP0001313 (Naringenin)

3D SDF for NP0001313 (Naringenin)

3D-SDF for NP0001313 (Naringenin)

PDB for NP0001313 (Naringenin)

3D PDB for NP0001313 (Naringenin)

SMILES for NP0001313 (Naringenin)

INCHI for NP0001313 (Naringenin)

Structure for NP0001313 (Naringenin)

3D Structure for NP0001313 (Naringenin)