NP-MRD: Showing NP-Card for Dihydrochalcone (NP0055285)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 01:23:41 UTC

Updated at

2022-04-28 01:23:41 UTC

NP-MRD ID

NP0055285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrochalcone

Description

1,3-Diphenyl-1-propanone, also known as benzyl acetophenone or hydrochalcone, belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 1,3-diphenyl-1-propanone is considered to be a flavonoid lipid molecule. 1,3-Diphenyl-1-propanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 1,3-Diphenyl-1-propanone has been detected, but not quantified in, mushrooms. Dihydrochalcone is found in Phallus impudicus . This could make 1,3-diphenyl-1-propanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -0.2259   -1.5636   -0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374   -0.4500   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705    0.6398   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229    0.4427   -1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216    0.1686   -0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254   -1.0965   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -1.3470    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2241   -0.3149    1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    0.9708    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183    1.2035    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340   -0.2787    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7765   -1.2951    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -1.1721    1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7590   -0.0054    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1177    1.0256    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8121    0.9012   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834    0.8159   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520    1.5649   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.3083   -2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461    1.3932   -2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539   -1.9604   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9756   -2.3559    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9552   -0.5218    2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3089    1.7645    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356    2.2237    0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.2362    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5807   -1.9658    1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7774    0.0945    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7007    1.9274    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    1.7353   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  5  1  0
 16 11  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1652304272018512D          

 16 17  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 13  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(CCC1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2

> <INCHI_KEY>
QGGZBXOADPVUPN-UHFFFAOYSA-N

> <FORMULA>
C15H14O

> <MOLECULAR_WEIGHT>
210.2711

> <EXACT_MASS>
210.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.144274735938627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-diphenylpropan-1-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
3.809801819333333

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.810958390420573

> <JCHEM_PKA_STRONGEST_BASIC>
-7.451305654567253

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
65.7837

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrochalcone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.700   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.160   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.470   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.700   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.160   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    6   14                                                       
CONECT   11   12   13                                                       
CONECT   12   11   15                                                       
CONECT   13    7    8   11                                                  
CONECT   14    9   10   15                                                  
CONECT   15   12   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
1,3-Diphenyl-1-oxopropane	ChEBI
Benzyl acetophenone	ChEBI
beta-Phenylpropiophenone	ChEBI
Hydrochalcone	ChEBI
Hydrocinnamophenone	ChEBI
b-Phenylpropiophenone	Generator
Β-phenylpropiophenone	Generator
.omega.-benzyl acetophenone	HMDB
1, 3-Diphenyl-3-propanone	HMDB
1,3-Diphenyl-3-propanone	HMDB
2',4-Dihydroxy-alpha,beta-dihydrochalcone	HMDB
2-Phenethyl phenyl ketone	HMDB
3-Phenyl-propiophenone	HMDB
3-Phenylpropiophenone	HMDB
Benzylacetophenone	HMDB
Dihydrochalcone	HMDB
Laquo omegaraquo -benzyl acetophenone	HMDB
Omega-benzyl acetophenone	HMDB
Phenethyl phenyl ketone	HMDB
Phenyl phenethyl ketone	HMDB
W-Benzylacetophenone	HMDB

Chemical Formula

C₁₅H₁₄O

Average Mass

210.2711 Da

Monoisotopic Mass

210.10447 Da

IUPAC Name

1,3-diphenylpropan-1-one

Traditional Name

dihydrochalcone

CAS Registry Number

Not Available

SMILES

O=C(CCC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2

InChI Key

QGGZBXOADPVUPN-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
Phallus impudicus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones 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

Retro-dihydrochalcones

Alternative Parents

Substituents

Retro-dihydrochalcone
Alkyl-phenylketone
Butyrophenone
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Benzenoid
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydrochalcones (CHEBI:71231 )
Chalcones and dihydrochalcones (LMPK12120464 )

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	3.43	ALOGPS
logP	3.81	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	16.81	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.78 m³·mol⁻¹	ChemAxon
Polarizability	24.14 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