NP-MRD: Showing NP-Card for (2S/2R)-naringenin (NP0331449)

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Record Information

Version

2.0

Created at

2023-01-14 16:25:29 UTC

Updated at

2024-09-03 04:15:47 UTC

NP-MRD ID

NP0331449

Natural Product DOI

https://doi.org/10.57994/0400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S/2R)-naringenin

Description

5,7-Dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one, also known as naringenin-7-sulfate or 4',5,7-trihydroxyflavanone, 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. 5,7-Dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one has been detected, but not quantified in, tea. This could make 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one a potential biomarker for the consumption of these foods. (2S/2R)-naringenin was first documented in 2023 (PMID: 36603655). A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4'.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.4135    2.7839   -1.3725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603    1.8154   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791    1.5074   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    0.1147   -0.6037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9200   -0.2523   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550   -0.6728    1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -1.0072    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850   -0.9365    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9000   -1.2736    0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.5154   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9371   -0.1822   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.8082   -0.1262 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7514   -0.4689   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7194   -1.4240    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472   -1.0761    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9945   -2.0523    0.5721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    0.1851    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277    1.1664   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557    2.4404   -0.5466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2061    0.8349   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    1.3919    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    2.2223   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.1874   -1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812   -0.7398    1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -1.3392    2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5682   -0.5989    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -0.4560   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    0.1470   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -2.4414    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2263   -2.1730    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292    0.4134    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016    3.2073   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 11  1  0
 11 10  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 10  8  1  0
 12  4  1  0
 13 20  1  0
  9 26  1  0
  7 25  1  0
  6 24  1  0
 11 28  1  0
 10 27  1  0
  4 23  1  6
  3 21  1  0
  3 22  1  0
 19 32  1  0
 17 31  1  0
 16 30  1  0
 14 29  1  0
M  END


  Mrv1652304271814002D          

 20 22  0  0  0  0            999 V2000
    5.0012    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1CC(=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

> <INCHI_KEY>
FTVWIRXFELQLPI-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.314576908172157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
86.99

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asahina

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-18         0                                  
HETATM    1  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    5   15   18                                                  
CONECT   12    7   15   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14    6   15   20                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Naringenin-7-sulfate	HMDB
4',5,7-Trihydroxyflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

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

Traditional Name

asahina

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CC(=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

InChI Key

FTVWIRXFELQLPI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.2, CD₃OD, simulated)	lpecio@iung.pulawy.pl	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
schidigera		Not Available

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

trihydroxyflavanone (CHEBI:50202 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

HMDB0128074

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016687

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Naringenin

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

932

PDB ID

Not Available

ChEBI ID

50202

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2S/2R)-naringenin (NP0331449)

MOL for NP0331449 ((2S/2R)-naringenin)

3D MOL for NP0331449 ((2S/2R)-naringenin)

3D SDF for NP0331449 ((2S/2R)-naringenin)

3D-SDF for NP0331449 ((2S/2R)-naringenin)

PDB for NP0331449 ((2S/2R)-naringenin)

3D PDB for NP0331449 ((2S/2R)-naringenin)

SMILES for NP0331449 ((2S/2R)-naringenin)

INCHI for NP0331449 ((2S/2R)-naringenin)

Structure for NP0331449 ((2S/2R)-naringenin)

3D Structure for NP0331449 ((2S/2R)-naringenin)