NP-MRD: Showing NP-Card for Naringin (NP0001395)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:20 UTC

Updated at

2024-09-03 04:21:46 UTC

NP-MRD ID

NP0001395

Natural Product DOI

https://doi.org/10.57994/2604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Naringin

Description

Naringin, also known as naringoside or naringin hydrate, is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. Naringin belongs to the flavonoid family. Flavonoids consist of 15 carbon atoms in 3 rings, 2 of which must be benzene rings connected by a 3 carbon chain. Naringin contains the basic flavonoid structure along with one rhamnose and one glucose unit attached to its aglycone portion, called naringenin, at the 7-carbon position. The steric hindrance provided by the two sugar units makes naringin less potent than its aglycone counterpart, naringenin. Naringin is a bitter tasting compound. Naringin is found, on average, in the highest concentration within a few different foods, such as rosemaries, grapefruit/pummelo hybrids, and grapefruits and in a lower concentration in grape wines, pummelo, and beers. Naringin has also been detected, but not quantified in several different foods, such as citrus, limes, herbs and spices, common oregano, and mandarin orange (clementine, tangerine). Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.

Structure

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

  Mrv1652305271900232D          

 41 45  0  0  1  0            999 V2000
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   20.3420  -13.8956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4965  -16.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6192  -11.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1999  -13.8846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1871  -10.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8721  -16.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8572  -12.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0612  -15.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1967  -13.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4296  -13.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4296  -16.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6256  -13.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0006  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 31  1  0  0  0  0
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 34 41  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
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   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652305271900232D          

 41 45  0  0  1  0            999 V2000
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   18.8815  -15.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -14.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1441  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0006  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1441  -15.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -15.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8815  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -12.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0006  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
 21  1  1  6  0  0  0
 17  2  1  1  0  0  0
  2 31  1  0  0  0  0
  3 15  1  0  0  0  0
 22  4  1  6  0  0  0
 23  5  1  6  0  0  0
 24  6  1  1  0  0  0
 25  7  1  1  0  0  0
 26  8  1  6  0  0  0
  9 30  1  0  0  0  0
 10 32  1  0  0  0  0
 11 17  1  0  0  0  0
 11 19  1  0  0  0  0
 12 18  1  0  0  0  0
 12 20  1  0  0  0  0
 13 27  1  0  0  0  0
 13 33  1  0  0  0  0
 14 29  2  0  0  0  0
 19 15  1  1  0  0  0
 20 16  1  6  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  1  1  0  0  0
 28 29  1  0  0  0  0
 29 35  1  0  0  0  0
 30 35  2  0  0  0  0
 30 36  1  0  0  0  0
 31 36  2  0  0  0  0
 31 37  1  0  0  0  0
 32 38  2  0  0  0  0
 32 39  1  0  0  0  0
 33 35  1  0  0  0  0
 33 37  2  0  0  0  0
 34 40  2  0  0  0  0
 34 41  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
DFPMSGMNTNDNHN-ZPHOTFPESA-N

> <FORMULA>
C27H32O14

> <MOLECULAR_WEIGHT>
580.5346

> <EXACT_MASS>
580.179205732

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.192538149282456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.15688572199999937

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.530202112756454

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.579343377607254

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294490695

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999995

> <JCHEM_REFRACTIVITY>
134.30379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naringin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
   -3.6432    3.0484    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.3187    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3652    1.1083    1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7094   -0.9007    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3905    2.1854   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2314    1.1821   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0607    0.9797   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3590   -1.0567    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -2.1130    1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7639   -3.0363   -2.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0249   -4.1955   -2.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7144   -2.2992   -1.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821   -0.0121    1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6086   -0.2840    0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    2.0329    2.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0800    1.6532    3.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6586    0.8405   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -0.2322   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -2.2647   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -2.6612   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278   -4.0266    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.5601   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    2.1633    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388    2.8714    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    3.2158    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1021    2.7819   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3483    0.6937   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    0.3394   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7728   -0.0199    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117    0.0407    3.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716   -2.7886   -4.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403   -2.4583   -5.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -1.1806   -5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    0.2504   -4.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -3.4181   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -4.3962   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -3.0928   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.6704   -2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.9748    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2272   -0.8113    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.5669    3.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6745    1.8818    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    3.0122    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020    0.8773    4.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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 19 20  1  0
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 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
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 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 15  9  1  0
 24 18  1  0
 26 13  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  6
  6 47  1  6
  7 48  1  6
 10 49  1  0
 12 50  1  0
 15 51  1  0
 17 52  1  1
 19 53  1  0
 20 54  1  0
 22 55  1  0
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 24 57  1  0
 25 58  1  0
 25 59  1  0
 29 60  1  6
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 30 62  1  0
 31 63  1  0
 32 64  1  6
 33 65  1  0
 34 66  1  1
 35 67  1  0
 36 68  1  1
 37 69  1  0
 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      40.633 -24.388   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.972 -25.938   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.993 -31.313   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.621 -21.308   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      43.318 -28.998   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      45.956 -21.287   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      43.306 -25.918   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      43.283 -19.758   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      35.228 -30.649   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      25.867 -23.666   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      39.314 -28.243   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      43.301 -24.378   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      32.535 -25.976   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      32.535 -30.596   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      40.657 -30.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.968 -24.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.308 -26.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.964 -23.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.651 -29.008   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.631 -23.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.639 -25.928   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.958 -22.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.982 -28.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.625 -22.063   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.976 -26.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      43.289 -21.298   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.202 -26.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.202 -28.286   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.535 -29.056   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      35.245 -29.109   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.641 -26.714   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.201 -24.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.869 -26.746   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.868 -25.976   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.869 -28.286   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.641 -28.318   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      35.245 -25.922   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      27.201 -25.976   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      28.534 -23.666   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.534 -26.746   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      29.868 -24.436   0.000  0.00  0.00           C+0
CONECT    1   18   21                                                       
CONECT    2   17   31                                                       
CONECT    3   15                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8   26                                                            
CONECT    9   30                                                            
CONECT   10   32                                                            
CONECT   11   17   19                                                       
CONECT   12   18   20                                                       
CONECT   13   27   33                                                       
CONECT   14   29                                                            
CONECT   15    3   19                                                       
CONECT   16   20                                                            
CONECT   17    2   11   21                                                  
CONECT   18    1   12   22                                                  
CONECT   19   11   15   23                                                  
CONECT   20   12   16   24                                                  
CONECT   21    1   17   25                                                  
CONECT   22    4   18   26                                                  
CONECT   23    5   19   25                                                  
CONECT   24    6   20   26                                                  
CONECT   25    7   21   23                                                  
CONECT   26    8   22   24                                                  
CONECT   27   13   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   14   28   35                                                  
CONECT   30    9   35   36                                                  
CONECT   31    2   36   37                                                  
CONECT   32   10   38   39                                                  
CONECT   33   13   35   37                                                  
CONECT   34   27   40   41                                                  
CONECT   35   29   30   33                                                  
CONECT   36   30   31                                                       
CONECT   37   31   33                                                       
CONECT   38   32   40                                                       
CONECT   39   32   41                                                       
CONECT   40   34   38                                                       
CONECT   41   34   39                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

COMPND    HMDB0002927
HETATM    1  C1  UNL     1      -3.643   3.048   0.457  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.865   2.319   1.524  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.365   1.108   1.084  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.335   0.314   0.506  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.709  -0.901   0.164  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.674  -1.093  -1.213  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.217  -1.232  -1.695  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.399  -0.258  -1.182  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.752  -0.503  -0.458  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.229  -1.757  -0.157  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.385  -1.924   0.570  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.853  -3.219   0.865  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.126  -0.877   1.034  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.677   0.392   0.751  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.523   0.566   0.025  1.00  0.00           C  
HETATM   16  O5  UNL     1       3.432   1.457   1.224  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.596   1.365   1.982  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.829   1.558   1.197  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.824   2.369   1.705  1.00  0.00           C  
HETATM   20  C15 UNL     1       8.000   2.582   1.006  1.00  0.00           C  
HETATM   21  C16 UNL     1       8.223   1.992  -0.224  1.00  0.00           C  
HETATM   22  O6  UNL     1       9.391   2.185  -0.950  1.00  0.00           O  
HETATM   23  C17 UNL     1       7.231   1.182  -0.733  1.00  0.00           C  
HETATM   24  C18 UNL     1       6.061   0.980  -0.021  1.00  0.00           C  
HETATM   25  C19 UNL     1       4.743   0.044   2.722  1.00  0.00           C  
HETATM   26  C20 UNL     1       4.359  -1.057   1.809  1.00  0.00           C  
HETATM   27  O7  UNL     1       5.000  -2.113   1.653  1.00  0.00           O  
HETATM   28  O8  UNL     1      -1.309  -1.116  -3.080  1.00  0.00           O  
HETATM   29  C21 UNL     1      -1.942  -2.161  -3.688  1.00  0.00           C  
HETATM   30  C22 UNL     1      -2.794  -1.589  -4.820  1.00  0.00           C  
HETATM   31  O9  UNL     1      -3.739  -0.697  -4.368  1.00  0.00           O  
HETATM   32  C23 UNL     1      -2.764  -3.036  -2.809  1.00  0.00           C  
HETATM   33  O10 UNL     1      -2.025  -4.195  -2.474  1.00  0.00           O  
HETATM   34  C24 UNL     1      -3.306  -2.418  -1.581  1.00  0.00           C  
HETATM   35  O11 UNL     1      -4.714  -2.299  -1.628  1.00  0.00           O  
HETATM   36  C25 UNL     1      -4.482  -0.012   1.399  1.00  0.00           C  
HETATM   37  O12 UNL     1      -5.609  -0.284   0.588  1.00  0.00           O  
HETATM   38  C26 UNL     1      -4.873   1.067   2.345  1.00  0.00           C  
HETATM   39  O13 UNL     1      -6.041   1.737   1.918  1.00  0.00           O  
HETATM   40  C27 UNL     1      -3.791   2.033   2.686  1.00  0.00           C  
HETATM   41  O14 UNL     1      -3.080   1.653   3.830  1.00  0.00           O  
HETATM   42  H1  UNL     1      -3.801   4.086   0.762  1.00  0.00           H  
HETATM   43  H2  UNL     1      -3.018   3.056  -0.464  1.00  0.00           H  
HETATM   44  H3  UNL     1      -4.630   2.597   0.263  1.00  0.00           H  
HETATM   45  H4  UNL     1      -2.045   2.952   1.876  1.00  0.00           H  
HETATM   46  H5  UNL     1      -3.659   0.840  -0.436  1.00  0.00           H  
HETATM   47  H6  UNL     1      -3.154  -0.232  -1.722  1.00  0.00           H  
HETATM   48  H7  UNL     1      -0.897  -2.265  -1.495  1.00  0.00           H  
HETATM   49  H8  UNL     1       0.734  -2.661  -0.467  1.00  0.00           H  
HETATM   50  H9  UNL     1       2.328  -4.027   0.535  1.00  0.00           H  
HETATM   51  H10 UNL     1       1.176   1.560  -0.194  1.00  0.00           H  
HETATM   52  H11 UNL     1       4.532   2.163   2.770  1.00  0.00           H  
HETATM   53  H12 UNL     1       6.739   2.871   2.658  1.00  0.00           H  
HETATM   54  H13 UNL     1       8.792   3.216   1.390  1.00  0.00           H  
HETATM   55  H14 UNL     1      10.102   2.782  -0.558  1.00  0.00           H  
HETATM   56  H15 UNL     1       7.348   0.694  -1.690  1.00  0.00           H  
HETATM   57  H16 UNL     1       5.300   0.339  -0.444  1.00  0.00           H  
HETATM   58  H17 UNL     1       5.773  -0.020   3.074  1.00  0.00           H  
HETATM   59  H18 UNL     1       4.012   0.041   3.567  1.00  0.00           H  
HETATM   60  H19 UNL     1      -1.172  -2.789  -4.188  1.00  0.00           H  
HETATM   61  H20 UNL     1      -3.340  -2.458  -5.262  1.00  0.00           H  
HETATM   62  H21 UNL     1      -2.156  -1.181  -5.632  1.00  0.00           H  
HETATM   63  H22 UNL     1      -3.482   0.250  -4.459  1.00  0.00           H  
HETATM   64  H23 UNL     1      -3.621  -3.418  -3.417  1.00  0.00           H  
HETATM   65  H24 UNL     1      -2.073  -4.396  -1.521  1.00  0.00           H  
HETATM   66  H25 UNL     1      -3.122  -3.093  -0.693  1.00  0.00           H  
HETATM   67  H26 UNL     1      -5.075  -2.670  -2.472  1.00  0.00           H  
HETATM   68  H27 UNL     1      -4.275  -0.975   1.936  1.00  0.00           H  
HETATM   69  H28 UNL     1      -6.227  -0.811   1.155  1.00  0.00           H  
HETATM   70  H29 UNL     1      -5.182   0.567   3.309  1.00  0.00           H  
HETATM   71  H30 UNL     1      -6.674   1.882   2.640  1.00  0.00           H  
HETATM   72  H31 UNL     1      -4.284   3.012   2.944  1.00  0.00           H  
HETATM   73  H32 UNL     1      -3.502   0.877   4.271  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   40   45
CONECT    3    4
CONECT    4    5   36   46
CONECT    5    6
CONECT    6    7   34   47
CONECT    7    8   28   48
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   49
CONECT   11   12   13   13
CONECT   12   50
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   15   51
CONECT   16   17
CONECT   17   18   25   52
CONECT   18   19   19   24
CONECT   19   20   53
CONECT   20   21   21   54
CONECT   21   22   23
CONECT   22   55
CONECT   23   24   24   56
CONECT   24   57
CONECT   25   26   58   59
CONECT   26   27   27
CONECT   28   29
CONECT   29   30   32   60
CONECT   30   31   61   62
CONECT   31   63
CONECT   32   33   34   64
CONECT   33   65
CONECT   34   35   66
CONECT   35   67
CONECT   36   37   38   68
CONECT   37   69
CONECT   38   39   40   70
CONECT   39   71
CONECT   40   41   72
CONECT   41   73
END

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
   -3.6432    3.0484    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.3187    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3652    1.1083    1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.3141    0.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7094   -0.9007    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0926   -1.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2166   -1.2325   -1.6946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -0.2578   -1.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -0.5031   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.7569   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -1.9242    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -3.2195    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.8771    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766    0.3921    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226    0.5659    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320    1.4571    1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5962    1.3647    1.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8295    1.5581    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    2.3687    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000    2.5818    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226    1.9919   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.1854   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2314    1.1821   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0607    0.9797   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    0.0438    2.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -1.0567    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -2.1130    1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -1.1158   -3.0796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -2.1611   -3.6882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7944   -1.5890   -4.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.6967   -4.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -3.0363   -2.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0249   -4.1955   -2.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -2.4182   -1.5811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7144   -2.2992   -1.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821   -0.0121    1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6086   -0.2840    0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    2.0329    2.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0800    1.6532    3.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014    4.0863    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175    3.0557   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.5971    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.9523    1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    0.8405   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -0.2322   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -2.2647   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -2.6612   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278   -4.0266    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.5601   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    2.1633    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388    2.8714    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    3.2158    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1021    2.7819   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3483    0.6937   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    0.3394   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7728   -0.0199    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117    0.0407    3.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716   -2.7886   -4.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403   -2.4583   -5.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -1.1806   -5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    0.2504   -4.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -3.4181   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -4.3962   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -3.0928   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.6704   -2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.9748    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2272   -0.8113    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.5669    3.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6745    1.8818    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    3.0122    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020    0.8773    4.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 15  9  1  0
 24 18  1  0
 26 13  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  6
  6 47  1  6
  7 48  1  6
 10 49  1  0
 12 50  1  0
 15 51  1  0
 17 52  1  1
 19 53  1  0
 20 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 29 60  1  6
 30 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  6
 33 65  1  0
 34 66  1  1
 35 67  1  0
 36 68  1  1
 37 69  1  0
 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
M  END

View in JSmol

Synonyms

Value	Source
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]	ChEBI
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside	ChEBI
Naringenin 7-O-neohesperidoside	ChEBI
Naringoside	ChEBI
Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside]	Generator
Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside]	Generator
Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucoside	Generator
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucoside	Generator
4',5,7-Trihydroxyflavanone 7-rhamnoglucoside	HMDB
Cyclorel	HMDB
Aurantiin	HMDB
Naringenin-7-hesperidoside	HMDB
Naringin dihydrochalcone	HMDB
Naringin sodium	HMDB
4'5-DiOH-flavone-7-rhgluc	HMDB
Naringin hydrate	HMDB
Nobiletin	HMDB

Chemical Formula

C₂₇H₃₂O₁₄

Average Mass

580.5346 Da

Monoisotopic Mass

580.17921 Da

IUPAC Name

(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

naringin

CAS Registry Number

10236-47-2

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI Key

DFPMSGMNTNDNHN-ZPHOTFPESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
MLEV NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	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, 125 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, 500 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
Adiantum spp.	KNApSAcK Database	22123792
Aglaomorpha quercifolia	LOTUS Database	35616633
Ailanthus integrifolia	KNApSAcK Database	22123792
Centaurea spp.	KNApSAcK Database	22123792
Ceterach officinarum	KNApSAcK Database	22123792
Ceterach sp.	KNApSAcK Database	22123792
Cicer arietinum	LOTUS Database	35616633
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	KNAPSACK
Citrus aurantiifolia	FooDB	PHENOL EXPLORER
Citrus aurantium	KNApSAcK Database	22123792
Citrus decumana	KNApSAcK Database	22123792
Citrus grandis	KNApSAcK Database	22123792
Citrus grandis var.tomentosa	KNApSAcK Database	22123792
Citrus latipes	LOTUS Database	35616633
Citrus limon	KNApSAcK Database	22123792
Citrus maxima	FooDB	PHENOL EXPLORER
Citrus natsudaidai	KNApSAcK Database	22123792
Citrus paradisi	KNApSAcK Database	22123792
Citrus reticulata	KNApSAcK Database	22123792
Citrus sinensis	LOTUS Database	35616633
Citrus spp.	KNApSAcK Database	22123792
Citrus sudachi	KNApSAcK Database	22123792
Citrus trifoliata	Plant	KNApSAcK
Citrus unshiu	KNApSAcK Database	22123792
Citrus x microcarpa	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clymenia polyandra	-	KNApSAcK
Coriandrum sativum	LOTUS Database	35616633
Crocus sativus	Plant	KNApSAcK
Daphniphyllum angustifolium	LOTUS Database	35616633
Drynaria fortunei	KNApSAcK Database	22123792
Dryopteris crassirhizoma	KNApSAcK Database	22123792
Euphorbia condylocarpa	LOTUS Database	35616633
Evodiopanax spp.	KNApSAcK Database	22123792
Flemingia strobilifera	KNApSAcK Database	22123792
Fortunella sp.	KNApSAcK Database	22123792
Glandularia bipinnatifida	Plant	KNApSAcK
Glycyrrhiza glabra	KNApSAcK Database	22123792
Glycyrrhiza inflata	KNApSAcK Database	22123792
Glycyrrhiza uralensis	KNApSAcK Database	22123792
Holarrhena pubescens	LOTUS Database	35616633
Leptoshaeria maculans	-	KNApSAcK
Leptosphaeria maculans	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Musa acuminata	LOTUS Database	35616633
Neocheiropteris fortunei	Plant	KNApSAcK
Onopordum illyricum	LOTUS Database	35616633
Origanum majoricum	LOTUS Database	35616633
Origanum vulgare	KNApSAcK Database	22123792
Origanum X majoricum	FooDB	PHENOL EXPLORER
Podocarpus fasciculus	KNApSAcK Database	22123792
Poncirus trifoliata	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrrosia serpens	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Salvia officinalis	FooDB	PHENOL EXPLORER
Salvia rosmarinus	FooDB	PHENOL EXPLORER
Solanum tuberosum	KNApSAcK Database	22123792
Syzygium jambos	LOTUS Database	35616633
Taxus fuana	KNApSAcK Database	22123792
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Taxus yunnanensis	KNApSAcK Database	22123792
Thymus vulgaris	FooDB	PHENOL EXPLORER
Verbena hybrida	Plant	KNApSAcK
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:28819 )
dihydroxyflavanone (CHEBI:28819 )
neohesperidoside (CHEBI:28819 )
flavanones (C09789 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	83 °C	Not Available
Boiling Point	922.00 to 926.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1 mg/mL at 40 °C	Not Available
LogP	-0.44	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	4.06 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.16	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.3 m³·mol⁻¹	ChemAxon
Polarizability	56.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0002927

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Naringin

METLIN ID

3604

PubChem Compound

442428

PDB ID

Not Available

ChEBI ID

28819

Good Scents ID

rw1400021

References

General References

Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
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 ]
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 ]
Tanaka S, Sato T, Akimoto N, Yano M, Ito A: Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Biochem Pharmacol. 2004 Aug 1;68(3):433-9. [PubMed:15242810 ]
Zhang J, Brodbelt JS: Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. [PubMed:15565223 ]
Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M: The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Jpn J Cancer Res. 2001 Dec;92(12):1322-8. [PubMed:11749698 ]
Ishii K, Furuta T, Kasuya Y: Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine. J Agric Food Chem. 2000 Jan;48(1):56-9. [PubMed:10637051 ]
Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81. [PubMed:15351063 ]

Showing NP-Card for Naringin (NP0001395)

MOL for NP0001395 (Naringin)

3D MOL for NP0001395 (Naringin)

3D SDF for NP0001395 (Naringin)

3D-SDF for NP0001395 (Naringin)

PDB for NP0001395 (Naringin)

3D PDB for NP0001395 (Naringin)

SMILES for NP0001395 (Naringin)

INCHI for NP0001395 (Naringin)

Structure for NP0001395 (Naringin)

3D Structure for NP0001395 (Naringin)