NP-MRD: Showing NP-Card for 1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one (NP0317156)

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Record Information

Version

2.0

Created at

2022-09-11 16:50:38 UTC

Updated at

2022-09-11 16:50:38 UTC

NP-MRD ID

NP0317156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2,4,6-Trihydroxychalcone belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. 1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one is found in Helichrysum oreophilum. 1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one was first documented in 2012 (PMID: 22805439). Based on a literature review very few articles have been published on 2,4,6-trihydroxychalcone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112218502D          

 19 20  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 O   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
    3.5724   -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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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
    2.8579   -1.6500    0.0000 C   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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317156

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
JEPSZTLDPWGHPQ-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.257

> <EXACT_MASS>
256.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.11938198965972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.9796293439999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.793095026088281

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.604985075853442

> <JCHEM_PKA_STRONGEST_BASIC>
-5.74325127964192

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.81970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   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

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

JEPSZTLDPWGHPQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helichrysum oreophilum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retrochalcones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	2.98	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-5.7	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	3	ChemAxon
Refractivity	72.82 m³·mol⁻¹	ChemAxon
Polarizability	26.12 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

53951317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun LP, Gao LX, Ma WP, Nan FJ, Li J, Piao HR: Synthesis and biological evaluation of 2,4,6-trihydroxychalcone derivatives as novel protein tyrosine phosphatase 1B inhibitors. Chem Biol Drug Des. 2012 Oct;80(4):584-90. doi: 10.1111/j.1747-0285.2012.01431.x. Epub 2012 Jul 13. [PubMed:22805439 ]
LOTUS database [Link]

Showing NP-Card for 1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one (NP0317156)

MOL for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D MOL for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D SDF for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D-SDF for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

PDB for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D PDB for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

SMILES for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

INCHI for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

Structure for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)

3D Structure for NP0317156 (1-phenyl-3-(2,4,6-trihydroxyphenyl)prop-2-en-1-one)