NP-MRD: Showing NP-Card for 4-hydroxychalcone (NP0333428)

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Record Information

Version

2.0

Created at

2024-06-18 20:17:49 UTC

Updated at

2024-09-03 04:22:26 UTC

NP-MRD ID

NP0333428

Natural Product DOI

https://doi.org/10.57994/2861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxychalcone

Description

(2E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one 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 (2E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-hydroxychalcone was first documented in 2011 (PMID: 20957597). It is generated by cyp2b6 and cyp2e1 enzymes via a p-hydroxylation-of-monosubstituted-benzene reaction (PMID: 25003119).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652308231921542D          

 19 20  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    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
   -0.7145    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    8.2500    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
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    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
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    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
   -1.4289    7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 H   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
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8+

> <INCHI_KEY>
PWWCDTYUYPOAIU-DHZHZOJOSA-N

> <FORMULA>
C15H12O2

> <MOLECULAR_WEIGHT>
224.259

> <EXACT_MASS>
224.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
24.76051387521783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.586759987333333

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.49969723858311

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.035390452246892

> <JCHEM_PKA_STRONGEST_BASIC>
-6.3529391887816375

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.8579

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxychalcone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   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      -1.334   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  15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.336  16.170   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      -2.667  13.860   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      -5.335  10.780   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   13                                                       
CONECT    6    9   12                                                       
CONECT    7   10   12                                                       
CONECT    8   11   12   18                                                  
CONECT    9    6   14                                                       
CONECT   10    7   14                                                       
CONECT   11    8   15   19                                                  
CONECT   12    6    7    8                                                  
CONECT   13    4    5   15                                                  
CONECT   14    9   10   16                                                  
CONECT   15   11   13   17                                                  
CONECT   16   14                                                            
CONECT   17   15                                                            
CONECT   18    8                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₂

Average Mass

224.2590 Da

Monoisotopic Mass

224.08373 Da

IUPAC Name

(2E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one

Traditional Name

4-hydroxychalcone

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8+

InChI Key

PWWCDTYUYPOAIU-DHZHZOJOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800, CD₃OD, simulated)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-06-18	View Spectrum

Species

Species of Origin

Not Available

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:34423 )
chalcones (CHEBI:34423 )

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	3.79	ALOGPS
logP	3.59	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.86 m³·mol⁻¹	ChemAxon
Polarizability	24.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0141386

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445524

KEGG Compound ID

C14231

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282361

PDB ID

Not Available

ChEBI ID

34423

Good Scents ID

Not Available

References

General References

Mueller M, Beck V, Jungbauer A: PPARalpha activation by culinary herbs and spices. Planta Med. 2011 Mar;77(5):497-504. doi: 10.1055/s-0030-1250435. Epub 2010 Oct 18. [PubMed:20957597 ]
Qu Q, Dai B, Yang B, Li X, Liu Y, Zhang F: 4-Hydroxychalcone attenuates hyperaldosteronism, inflammation, and renal injury in cryptochrome-null mice. Biomed Res Int. 2014;2014:603415. doi: 10.1155/2014/603415. Epub 2014 Jun 9. [PubMed:25003119 ]

Showing NP-Card for 4-hydroxychalcone (NP0333428)

MOL for NP0333428 (4-hydroxychalcone)

3D MOL for NP0333428 (4-hydroxychalcone)

3D SDF for NP0333428 (4-hydroxychalcone)

3D-SDF for NP0333428 (4-hydroxychalcone)

PDB for NP0333428 (4-hydroxychalcone)

3D PDB for NP0333428 (4-hydroxychalcone)

SMILES for NP0333428 (4-hydroxychalcone)

INCHI for NP0333428 (4-hydroxychalcone)

Structure for NP0333428 (4-hydroxychalcone)

3D Structure for NP0333428 (4-hydroxychalcone)