NP-MRD: Showing NP-Card for 5,7-Dimethoxyflavanone (NP0138464)

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Record Information

Version

2.0

Created at

2022-06-29 17:30:45 UTC

Updated at

2022-06-29 17:30:45 UTC

NP-MRD ID

NP0138464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dimethoxyflavanone

Description

Pinocembrin 5,7-dimethyl ether belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, pinocembrin 5,7-dimethyl ether is considered to be a flavonoid lipid molecule. 5,7-Dimethoxyflavanone is found in Boesenbergia rotunda, Cedrelopsis grevei, Eucalyptus sieberi, Kaempferia parviflora, Leptospermum scoparium and Piper methysticum. Pinocembrin 5,7-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.2598    1.5381   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    1.8070   -0.9318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    0.9007   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1933   -0.3652   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -1.2230    0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215   -2.4965    0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -2.9207    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385   -0.8390    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378    0.4301   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.2681   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803    0.7806   -0.3377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    0.2955    0.5457 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1260    0.6709    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389    0.5576   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8328    0.9271   -1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295    1.4167   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121    1.5264    0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0369    1.1580    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481   -1.1846    0.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.6870    0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -2.9202    0.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6995    1.5701    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4673    0.5201   -1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7871    2.3322   -1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -0.6544   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8499   -4.0159    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2772   -2.6924   -0.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2685   -2.4430    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446    2.2491   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773    0.7983    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.1880   -1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1818    0.8462   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433    1.7001   -0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.8986    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091    1.2504    2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052   -1.4314    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367   -1.7566    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8 20  1  0
 20 21  2  0
 20 19  1  0
 19 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10  3  1  0
 18 13  1  0
  9  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 19 36  1  0
 19 37  1  0
 12 30  1  1
 10 29  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv1533004191519152D          

 21 23  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    2.8579    0.8250    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 12 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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-9,14H,10H2,1-2H3

> <INCHI_KEY>
IAFBOKYTDSDNHV-UHFFFAOYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.311

> <EXACT_MASS>
284.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.34346587603366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.780461484

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.123917142431562

> <JCHEM_PKA_STRONGEST_BASIC>
-4.422979726784875

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
78.27350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinocembrin 5,7-dimethyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    3                                                       
CONECT   16   12   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₄

Average Mass

284.3110 Da

Monoisotopic Mass

284.10486 Da

IUPAC Name

5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

pinocembrin 5,7-dimethyl ether

CAS Registry Number

1036-72-2

SMILES

COC1=CC(OC)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H16O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-9,14H,10H2,1-2H3

InChI Key

IAFBOKYTDSDNHV-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
Boesenbergia rotunda	LOTUS Database	35616633
Cedrelopsis grevei	LOTUS Database	35616633
Eucalyptus sieberi	LOTUS Database	35616633
Kaempferia parviflora	LOTUS Database	35616633
Leptospermum scoparium	LOTUS Database	35616633
Piper methysticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavanone
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140217 )

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	3.11	ALOGPS
logP	2.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.27 m³·mol⁻¹	ChemAxon
Polarizability	30.34 Å³	ChemAxon
Number of Rings	3	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

378567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7-Dimethoxyflavanone (NP0138464)

MOL for NP0138464 (5,7-Dimethoxyflavanone)

3D MOL for NP0138464 (5,7-Dimethoxyflavanone)

3D SDF for NP0138464 (5,7-Dimethoxyflavanone)

3D-SDF for NP0138464 (5,7-Dimethoxyflavanone)

PDB for NP0138464 (5,7-Dimethoxyflavanone)

3D PDB for NP0138464 (5,7-Dimethoxyflavanone)

SMILES for NP0138464 (5,7-Dimethoxyflavanone)

INCHI for NP0138464 (5,7-Dimethoxyflavanone)

Structure for NP0138464 (5,7-Dimethoxyflavanone)

3D Structure for NP0138464 (5,7-Dimethoxyflavanone)