NP-MRD: Showing NP-Card for 2',4',6'-Trihydroxydihydrochalcone (NP0055292)

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Record Information

Version

2.0

Created at

2022-04-28 01:23:52 UTC

Updated at

2022-04-28 01:23:52 UTC

NP-MRD ID

NP0055292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',4',6'-Trihydroxydihydrochalcone

Description

3-Phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one is considered to be a flavonoid lipid molecule. 2',4',6'-Trihydroxydihydrochalcone is found in Greyia flanaganii, Helichrysum tenuifolium, Lindera umbellata , Piper lolot, Populus angustifolia, Populus balsamifera , Populus deltoides and Populus nigra . 3-Phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.7126    2.5050   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488    1.2389   -0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406    0.5514   -0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    0.5169    0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -0.1548    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558    0.5767    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    0.0222    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -1.3255    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -2.0691    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -1.5000    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350    0.6987   -0.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922   -0.6404   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2219   -1.5751   -0.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836   -1.1272    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5882   -0.3412    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8666   -0.8542    0.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4377    0.9832   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655    1.5131   -0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    2.8473   -0.7683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704   -0.3533   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115    1.2641   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    1.5986    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551    0.0519    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295    1.6438   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002    0.6119   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0602   -1.7999    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -3.1227    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030   -2.1070    0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3399   -1.8064   -0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271   -2.1815    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0938   -0.8131    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3056    1.6209   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457    3.5269   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 11 18  1  0
 18 19  1  0
 18 17  2  0
 17 15  1  0
 10  5  1  0
 16 31  1  0
 14 30  1  0
 13 29  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 19 33  1  0
 17 32  1  0
M  END


  Mrv1652308201922462D          

 19 20  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-5,8-9,16,18-19H,6-7H2

> <INCHI_KEY>
QWQGMMRHTWIOGH-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.80445511913816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
4.199105854333333

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.678851177088557

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.970994168911226

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6084188224106635

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.7264

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8   11   13                                                       
CONECT    9   11   14                                                       
CONECT   10    4    5    6                                                  
CONECT   11    8    9   16                                                  
CONECT   12    7   15   17                                                  
CONECT   13    8   15   18                                                  
CONECT   14    9   15   19                                                  
CONECT   15   12   13   14                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

Traditional Name

3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C15H14O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-5,8-9,16,18-19H,6-7H2

InChI Key

QWQGMMRHTWIOGH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Greyia flanaganii	LOTUS Database	35616633
Helichrysum tenuifolium	Plant	KNApSAcK
Lindera umbellata	Plant	KNApSAcK
Piper lolot	LOTUS Database	35616633
Populus angustifolia	Plant	KNApSAcK
Populus balsamifera	Plant	KNApSAcK
Populus deltoides	Plant	KNApSAcK
Populus nigra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phloroglucinol derivative
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120510 )

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	2.85	ALOGPS
logP	4.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.73 m³·mol⁻¹	ChemAxon
Polarizability	26.8 Å³	ChemAxon
Number of Rings	2	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

HMDB0128079

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB086935

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1226045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',4',6'-Trihydroxydihydrochalcone (NP0055292)

MOL for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

3D MOL for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

3D SDF for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

3D-SDF for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

PDB for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

3D PDB for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

SMILES for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

INCHI for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

Structure for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)

3D Structure for NP0055292 (2',4',6'-Trihydroxydihydrochalcone)