NP-MRD: Showing NP-Card for 5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0253463)

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Record Information

Version

2.0

Created at

2022-09-07 17:20:04 UTC

Updated at

2022-09-07 17:20:04 UTC

NP-MRD ID

NP0253463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

Description

4',5,8-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. Thus, 4',5,8-trihydroxyflavanone is considered to be a flavonoid lipid molecule. 4',5,8-Trihydroxyflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',5,8-Trihydroxyflavanone has been detected, but not quantified in, green vegetables and spinachs. 5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one is found in Artemisia campestris and Spinacia oleracea. This could make 4',5,8-trihydroxyflavanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3307   -0.4478   -2.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7632    0.0698   -1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    0.7020   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648    0.5414   -0.1519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7424    0.0429   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -1.2922   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3336   -1.7164   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837   -0.8049   -0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6861   -1.2275   -1.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887    0.5448   -0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9357   -0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775   -0.2227    0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -0.0875    1.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929   -0.1019    2.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4019   -0.2549    3.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5576    0.0393    2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3733    0.1941    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890    0.2086    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    0.3656   -1.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.0683   -0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    1.7835   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0946    0.2886   -2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776    1.5813    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -2.0008   -0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -2.7571   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2557   -1.4169   -0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8985    1.2582   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5440    1.9978   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -0.3586    3.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489    0.0330    3.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    0.3077    1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2693    0.4075   -1.9491 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 16  2  0
 16 14  1  0
 14 15  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  1
  3 21  1  0
  3 22  1  0
 19 32  1  0
 17 31  1  0
 16 30  1  0
 15 29  1  0
M  END


  Mrv0541 05061306092D          

 20 22  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
  6  5  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  1  0  0  0  0
 11  6  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 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  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 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1

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

> <INCHI_KEY>
SMRHIFAZRRVAQZ-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.16110562996326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.835108050333333

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.985223598907567

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.31357769798091

> <JCHEM_PKA_STRONGEST_BASIC>
-4.074339405056507

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -0.770   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    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5   14   17                                                  
CONECT   11    6   15   18                                                  
CONECT   12    7   14   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14   10   12   15                                                  
CONECT   15   11   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
3-Ethyl-7-(trifluoromethyl)-2-quinoxalinol	HMDB
5,8,4'-Trihydroxyflavanone	HMDB
7-Trifluoromethyl-3-ethyl-2(1H)-quinoxalinone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1

InChI Identifier

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

InChI Key

SMRHIFAZRRVAQZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia campestris	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633

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

4'-hydroxyflavonoid
5-hydroxyflavonoid
8-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Chromone
Chromane
1-benzopyran
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
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

Flavanones (LMPK12140104 )

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	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.1	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	27.16 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

HMDB0031824

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008502

KNApSAcK ID

C00008392

Chemspider ID

24846274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0253463)

MOL for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0253463 (5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)