NP-MRD: Showing NP-Card for 3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one (NP0283463)

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Record Information

Version

2.0

Created at

2022-09-09 10:43:50 UTC

Updated at

2022-09-09 10:43:50 UTC

NP-MRD ID

NP0283463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Pinocembrin chalcone belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Pinocembrin chalcone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, pinocembrin chalcone has been detected, but not quantified in, several different foods, such as other cereal products, sourdoughs, malus (crab apple), pineappple sages, and capers. 3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one is found in Alpinia zerumbet, Boesenbergia rotunda, Helichrysum acutatum, Helichrysum forskahlii, Helichrysum trilineatum and Piper sarmentosum. This could make pinocembrin chalcone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.8189    2.2441   -0.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708    0.9600   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    0.3345   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314    1.1091   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350    0.5354   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -0.8102   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -1.2992   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4241   -0.4311   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    0.9296   -0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346    1.3742   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1524    0.2909   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    1.1155   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    2.4580   -0.1770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5621    0.5090   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6371   -0.8478    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8719   -1.4851    0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224   -1.6468    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646   -1.0797    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -1.9018    0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404   -0.7239   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.1880   -0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -1.5504   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4993   -2.3799   -0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157   -0.8736   -0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0915    1.5833   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    2.4643   -0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7559    3.2184   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4767    1.0845   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2953   -1.7451   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651   -2.7274    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703   -2.8967    0.0911 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  2  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 29  1  0
 14 28  1  0
 13 27  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 19 31  1  0
 17 30  1  0
M  END


  Mrv1652309131719512D          

 19 20  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    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
    3.5724    3.7125    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
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    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
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    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  2  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
  7 12  1  4  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>
NP0283463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C(=O)C=CC2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-9,16,18-19H

> <INCHI_KEY>
LOYXTWZXLWHMBX-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.257

> <EXACT_MASS>
256.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.31970437392721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
4.279629344

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.24289383541464

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9973036039015994

> <JCHEM_PKA_STRONGEST_BASIC>
-6.327031656025134

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.8197

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-17         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   9.240   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

C₁₅H₁₂O₄

Average Mass

256.2570 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C(=O)C=CC2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C15H12O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-9,16,18-19H

InChI Key

LOYXTWZXLWHMBX-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
Alpinia zerumbet	LOTUS Database	35616633
Boesenbergia rotunda	LOTUS Database	35616633
Helichrysum acutatum	LOTUS Database	35616633
Helichrysum forskahlii	LOTUS Database	35616633
Helichrysum trilineatum	LOTUS Database	35616633
Piper sarmentosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone 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'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-6993 )

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	3.14	ALOGPS
logP	4.28	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.82 m³·mol⁻¹	ChemAxon
Polarizability	26.32 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

HMDB0128077

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031121

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

460718

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one (NP0283463)

MOL for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D MOL for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D SDF for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D-SDF for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

PDB for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D PDB for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

SMILES for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

INCHI for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

Structure for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D Structure for NP0283463 (3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)