NP-MRD: Showing NP-Card for 4,4'-Dihydroxychalcone (NP0054628)

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Record Information

Version

2.0

Created at

2022-04-28 00:55:19 UTC

Updated at

2022-04-28 00:55:19 UTC

NP-MRD ID

NP0054628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-Dihydroxychalcone

Description

4,4'-Dihydroxychalcone, also known as RVC 588, 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. Thus, 4,4'-dihydroxychalcone is considered to be a flavonoid. 4,4'-Dihydroxychalcone is found in Abies spectabilis, Alpinia blepharocalyx , Alpinia roxburghii, Araucaria angustifolia and Chamaecyparis obtusa. 4,4'-Dihydroxychalcone was first documented in 2011 (PMID: 21922913). Based on a literature review very few articles have been published on 4,4'-Dihydroxychalcone (PMID: 34705327).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.0273   -2.2616    1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -1.1831    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742   -0.5428    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805   -1.0520    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683   -0.4075   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.0214    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -0.5009   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9123    0.6770   -1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1126    1.2274   -1.4545 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7133    1.3135   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5166    0.7690   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167   -0.5872    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.5978   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.1109   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0360    0.4656    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2990    1.0161    0.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8341   -0.7225    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5668   -1.2184    1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.3895   -0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.9936    0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234   -1.9663    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -1.0069   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6052    1.8638   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164    2.2650   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6144    1.3040   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    1.1464   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0691    2.0515   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6827    1.6481    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -1.2306    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -2.1508    1.5557 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  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 11  1  0
 11 10  2  0
 10  8  1  0
 18 12  1  0
  9 23  1  0
  7 22  1  0
  6 21  1  0
  4 20  1  0
  3 19  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 11 25  1  0
 10 24  1  0
M  END


  Mrv1652304282202552D          

 18 19  0  0  0  0            999 V2000
    2.8579   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    2.1434   -2.8875    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
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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
    1.4289   -6.6000    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   -7.8375    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
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054628

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3/c16-13-6-1-11(2-7-13)3-10-15(18)12-4-8-14(17)9-5-12/h1-10,16-17H/b10-3+

> <INCHI_KEY>
FZQLEXXZAVVCCA-XCVCLJGOSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.258

> <EXACT_MASS>
240.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.80738964306871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.283194665666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.06431232365595

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.844342485315634

> <JCHEM_PKA_STRONGEST_BASIC>
-6.35293918773477

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
70.8388

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dihydroxybenzylidene acetophenone	MeSH
RVC 588	MeSH
RVC-588	MeSH

Chemical Formula

C₁₅H₁₂O₃

Average Mass

240.2580 Da

Monoisotopic Mass

240.07864 Da

IUPAC Name

(2E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H12O3/c16-13-6-1-11(2-7-13)3-10-15(18)12-4-8-14(17)9-5-12/h1-10,16-17H/b10-3+

InChI Key

FZQLEXXZAVVCCA-XCVCLJGOSA-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
Abies spectabilis	LOTUS Database	35616633
Alpinia blepharocalyx	Plant	KNApSAcK
Alpinia roxburghii	LOTUS Database	35616633
Araucaria angustifolia	LOTUS Database	35616633
Chamaecyparis obtusa	Plant	KNApSAcK

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

Chalcones and dihydrochalcones (LMPK12120193 )

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	3.19	ALOGPS
logP	3.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.84 m³·mol⁻¹	ChemAxon
Polarizability	25.81 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

C00006919

Chemspider ID

4578417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5467477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saied S, Shah S, Ali Z, Khan A, Marasini BP, Choudhary MI: Chemical constituents of Cichorium intybus and their inhibitory effects against urease and alpha-chymotrypsin enzymes. Nat Prod Commun. 2011 Aug;6(8):1117-20. [PubMed:21922913 ]
Thanh Huong L, Anh Thu P, Thi Dao P, Thi Mai Huong D, Van Cuong P, Hai Dang N: Anti-Inflammatory Properties of Longifuran A, a New Benzofuran from the Stems of Amomum longiligulare. Chem Biodivers. 2021 Dec;18(12):e2100518. doi: 10.1002/cbdv.202100518. Epub 2021 Nov 16. [PubMed:34705327 ]

Showing NP-Card for 4,4'-Dihydroxychalcone (NP0054628)

MOL for NP0054628 (4,4'-Dihydroxychalcone)

3D MOL for NP0054628 (4,4'-Dihydroxychalcone)

3D SDF for NP0054628 (4,4'-Dihydroxychalcone)

3D-SDF for NP0054628 (4,4'-Dihydroxychalcone)

PDB for NP0054628 (4,4'-Dihydroxychalcone)

3D PDB for NP0054628 (4,4'-Dihydroxychalcone)

SMILES for NP0054628 (4,4'-Dihydroxychalcone)

INCHI for NP0054628 (4,4'-Dihydroxychalcone)

Structure for NP0054628 (4,4'-Dihydroxychalcone)

3D Structure for NP0054628 (4,4'-Dihydroxychalcone)