NP-MRD: Showing NP-Card for Phlorizin (NP0001427)

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Record Information

Version

2.0

Created at

2012-09-11 21:47:48 UTC

Updated at

2025-02-11 15:44:04 UTC

NP-MRD ID

NP0001427

Natural Product DOI

https://doi.org/10.57994/2297

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phlorizin

Description

Phlorizin, also known as phlorizoside or phlorrhizen, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phlorizin (also referred to as phloridzin; chemical name phloretin-2'-‚âà√≠‚Äö√¢¬ß-D-glucopyranoside) is a glucoside of phloretin, a dihydrochalcone, a family of bicyclic flavonoids, which in turn is a subgroup in the diverse phenylpropanoid synthesis pathway in plants. In humans, phlorizin is involved in lactose degradation. Phlorizin is a bitter tasting compound. Phlorizin is found, on average, in the highest concentration in a few different foods, such as mexican oregano, european plums, and apples and in a lower concentration in pomegranates and apricots. Phlorizin has also been detected, but not quantified, in several different foods, such as epazotes, durians, chinese broccoli, sesames, and sweet potato. This could make phlorizin a potential biomarker for the consumption of these foods. It is of sweet taste and contains four molecules of water in the crystal. Phlorizin is found primarily in unripe Malus (apple), root bark of apple, trace amounts have been found in strawberry. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Closely related species, such as pear (Pyrus communis), cherry, and other fruit trees in the Rosaceae do not contain phloridzin. Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as empagliflozin, canagliflozin and dapagliflozin. Phlorizin is a competitive inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this reduces renal glucose transport, lowering the amount of glucose in the blood. Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine. Above 200 °C, it decomposes.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305271900262D          

 31 33  0  0  0  0            999 V2000
   -0.7131   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430    1.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    1.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    2.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    2.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.6567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4280   -2.4817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1430   -2.8942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8580   -2.4817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8580   -1.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1430   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -2.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -2.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -1.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -1.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  6  0  0  0
 23 24  1  0  0  0  0
 23 28  1  1  0  0  0
 24 25  1  0  0  0  0
 24 29  1  6  0  0  0
 25 26  1  0  0  0  0
 25 30  1  1  0  0  0
 30 31  1  0  0  0  0
 21  1  1  1  0  0  0
M  END

  Mrv1652305271900262D          

 31 33  0  0  0  0            999 V2000
   -0.7131   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430    1.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    1.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    2.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    2.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.6567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4280   -2.4817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1430   -2.8942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8580   -2.4817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8580   -1.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1430   -1.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -2.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -2.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -1.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -1.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  6  0  0  0
 23 24  1  0  0  0  0
 23 28  1  1  0  0  0
 24 25  1  0  0  0  0
 24 29  1  6  0  0  0
 25 26  1  0  0  0  0
 25 30  1  1  0  0  0
 30 31  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0001427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
IOUVKUPGCMBWBT-QNDFHXLGSA-N

> <FORMULA>
C21H24O10

> <MOLECULAR_WEIGHT>
436.4093

> <EXACT_MASS>
436.136946988

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35851023236527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.9774724393333329

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.353052451271898

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.869757605270291

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346304827

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
105.85169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phlorizin

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.331  -2.323   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.331  -0.783   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.666  -0.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.666   1.527   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.000   2.298   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.331   2.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   1.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001  -0.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.336  -0.783   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.336  -2.323   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.336   2.298   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.668  -0.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.668   1.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.003   2.298   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.337   1.527   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.670   2.298   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.003   3.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.337   4.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.670   3.838   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.004   4.608   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.666  -3.093   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.666  -4.633   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.000  -5.403   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -4.633   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -3.093   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.000  -2.323   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.331  -5.403   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.000  -6.943   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.670  -5.403   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.670  -2.323   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.004  -3.093   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   19                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   16   18   20                                                  
CONECT   20   19                                                            
CONECT   21   22   26    1                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   30                                                  
CONECT   26   21   25                                                       
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Floridzin	ChEBI
Phloretin 2'-glucoside	ChEBI
Phlorhizin	ChEBI
Phloridzin	ChEBI
Phlorizoside	ChEBI
Phloretin-2'-beta-glucoside	HMDB
Phloretin-2'-O-beta-glucoside	HMDB
Phloridzinum	HMDB
Phloridzosid	HMDB
Phlorizine	HMDB
Phlorrhizen	HMDB
Phlorrhizin	HMDB

Chemical Formula

C₂₁H₂₄O₁₀

Average Mass

436.4093 Da

Monoisotopic Mass

436.13695 Da

IUPAC Name

1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one

Traditional Name

phlorizin

CAS Registry Number

60-81-1

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1

InChI Key

IOUVKUPGCMBWBT-QNDFHXLGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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	2024-05-03	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	2024-05-03	View Spectrum
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	2024-05-03	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	2024-05-03	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	2024-05-03	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	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.54 MHz, DMSO-d6, 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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Cinnamomum subavenium		LOTUS database
Citrus sinensis		LOTUS database
Cynomorium songaricum		LOTUS database
Dianthus caryophyllus	Plant	KNApSAcK
Flemingia strobilifera	Plant	KNApSAcK
Fragaria x ananassa		LOTUS database
Kalmia latifolia	Plant	KNApSAcK
Lactuca sativa	FooDB	16666434
Lippia graveolens		LOTUS database
Litchi chinensis	Plant	KNApSAcK
Lithocarpus liseifolius	Plant	KNApSAcK
Lithocarpus litseifolius		LOTUS database
Lithocarpus pachyphyllus		LOTUS database
Lithocarpus polystachyus		LOTUS database
Lithophragma affine	Plant	KNApSAcK
Loiseleuria procumbens (L.) Desv.	Plant	KNApSAcK
Malus	FooDB	KNAPSACK
Malus domestica	Plant	KNApSAcK
Malus doumeri		LOTUS database
Malus doumeri varl formosana	Plant	KNApSAcK
Malus pumila	FooDB	9818410
Malus spp.	Plant	KNApSAcK
Malus sylvestris		LOTUS database
Micromelum minutum		LOTUS database
Pieris japonica	Plant	KNApSAcK
Posidonia oceanica	Plant	KNApSAcK
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	Plant	KNApSAcK
Prunus domestica	FooDB	PHENOL EXPLORER
Punica granatum	FooDB	PHENOL EXPLORER
Pyrus communis	FooDB	PHENOL EXPLORER
Rhododendron spp.	Plant	KNApSAcK
Symplocos lancifolia	Plant	KNApSAcK
Symplocos spicata	Plant	KNApSAcK
Vaccinium macrocarpon		LOTUS database
Vitis vinifera		LOTUS database

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Phenolic glycoside
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Butyrophenone
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Resorcinol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:8113 )
dihydrochalcones (CHEBI:8113 )
aryl beta-D-glucoside (CHEBI:8113 )
dihydrochalcones (C01604 )
Chalcones and dihydrochalcones (C01604 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	110.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/mL at 22 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.98	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.85 m³·mol⁻¹	ChemAxon
Polarizability	42.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0036634

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Phlorizin

METLIN ID

Not Available

PubChem Compound

6072

PDB ID

Not Available

ChEBI ID

8113

Good Scents ID

Not Available

References

General References

Jugde H, Nguy D, Moller I, Cooney JM, Atkinson RG: Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple. FEBS J. 2008 Aug;275(15):3804-14. doi: 10.1111/j.1742-4658.2008.06526.x. [PubMed:18573104 ]
Li N, Shi J, Wang K: Profile and antioxidant activity of phenolic extracts from 10 crabapples (Malus wild species). J Agric Food Chem. 2014 Jan 22;62(3):574-81. doi: 10.1021/jf404542d. Epub 2014 Jan 13. [PubMed:24392851 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Phlorizin (NP0001427)

MOL for NP0001427 (Phlorizin)

3D MOL for NP0001427 (Phlorizin)

3D SDF for NP0001427 (Phlorizin)

3D-SDF for NP0001427 (Phlorizin)

PDB for NP0001427 (Phlorizin)

3D PDB for NP0001427 (Phlorizin)

SMILES for NP0001427 (Phlorizin)

INCHI for NP0001427 (Phlorizin)

Structure for NP0001427 (Phlorizin)

3D Structure for NP0001427 (Phlorizin)