NP-MRD: Showing NP-Card for 3,7-Dimethoxy-5-hydroxyflavone (NP0052836)

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Record Information

Version

2.0

Created at

2022-04-27 23:45:03 UTC

Updated at

2022-04-27 23:45:03 UTC

NP-MRD ID

NP0052836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7-Dimethoxy-5-hydroxyflavone

Description

Galangin 3,7-dimethyl ether, also known as 3,7-dimethylgalangin, 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, galangin 3,7-dimethyl ether is considered to be a flavonoid lipid molecule. 3,7-Dimethoxy-5-hydroxyflavone is found in Boesenbergia pandurata , Boesenbergia rotunda, Cheilanthes kaulfussii, Cryptocarya chinensis, Escallonia langleyensis, Escallonia leucantha, Heliotropium huascoense, Heliotropium huascuense, Heliotropium megalanthum, Heliotropium pycnophyllum, Kaempferia parviflora , Muntingia calabura, Notholaena ekmanii, Notholaena spp., Platyzoma microphyllum, Pseudognaphalium cheiranthifolium and Pseudognaphalium viscosum. Galangin 3,7-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    5.7502   -1.6736   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766   -2.0151   -0.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -1.0298   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.2764    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    1.1949    0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0472    2.5437    0.6990 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    0.8392    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    1.7397    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369    2.9353    0.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856    1.3198    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8735    2.2652    0.8360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4112    3.0540   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.0178    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -0.5744    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583    0.0173    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8954   -0.5895    0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108   -1.8650   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495   -2.4913   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -1.8618   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -0.7893    0.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008   -0.4643    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1143   -1.3949   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471   -1.5603    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -2.5102   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979   -0.7551   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151    0.5783    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0222    2.8164    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    2.3712   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6346    3.5945   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535    3.7471    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6762    0.9868    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8027   -0.0951    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9624   -2.3535   -0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661   -3.4818   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -2.3893   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -2.4032   -0.2803 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 20  1  0
 20 21  1  0
 21 22  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 22  3  1  0
 19 14  1  0
 21  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 22 36  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

  Mrv0541 04121514282D          

 22 24  0  0  0  0            999 V2000
    0.0000   -2.4750    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 O   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   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
    0.0000    0.8250    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052836

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O5/c1-20-11-8-12(18)14-13(9-11)22-16(17(21-2)15(14)19)10-6-4-3-5-7-10/h3-9,18H,1-2H3

> <INCHI_KEY>
OYCOUDKDRFJOCP-UHFFFAOYSA-N

> <FORMULA>
C17H14O5

> <MOLECULAR_WEIGHT>
298.294

> <EXACT_MASS>
298.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.641116103115067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3,7-dimethoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.0221515526666662

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.155960202938623

> <JCHEM_PKA_STRONGEST_BASIC>
-4.567901770840156

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
82.13390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galangin 3,7-dimethyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   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  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   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       5.335  -4.620   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  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,7-Dimethylgalangin	MeSH
Hydroxy-37-dimethoxyflavone	ChEMBL

Chemical Formula

C₁₇H₁₄O₅

Average Mass

298.2940 Da

Monoisotopic Mass

298.08412 Da

IUPAC Name

5-hydroxy-3,7-dimethoxy-2-phenyl-4H-chromen-4-one

Traditional Name

galangin 3,7-dimethyl ether

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H14O5/c1-20-11-8-12(18)14-13(9-11)22-16(17(21-2)15(14)19)10-6-4-3-5-7-10/h3-9,18H,1-2H3

InChI Key

OYCOUDKDRFJOCP-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
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Cheilanthes kaulfussii	Plant	KNApSAcK
Cryptocarya chinensis	LOTUS Database	35616633
Escallonia langleyensis	Plant	KNApSAcK
Escallonia leucantha	Plant	KNApSAcK
Heliotropium huascoense	Plant	KNApSAcK
Heliotropium huascuense	Plant	KNApSAcK
Heliotropium megalanthum	Plant	KNApSAcK
Heliotropium pycnophyllum	Plant	KNApSAcK
Kaempferia parviflora	Plant	KNApSAcK
Muntingia calabura	LOTUS Database	35616633
Notholaena ekmanii	Plant	KNApSAcK
Notholaena spp.	Plant	KNApSAcK
Platyzoma microphyllum	Plant	KNApSAcK
Pseudognaphalium cheiranthifolium	Plant	KNApSAcK
Pseudognaphalium viscosum	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

3-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111657 )

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	3.74	ALOGPS
logP	3.02	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.13 m³·mol⁻¹	ChemAxon
Polarizability	30.64 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

5748697

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,7-Dimethoxy-5-hydroxyflavone (NP0052836)

MOL for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

3D MOL for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

3D SDF for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

3D-SDF for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

PDB for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

3D PDB for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

SMILES for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

INCHI for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

Structure for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)

3D Structure for NP0052836 (3,7-Dimethoxy-5-hydroxyflavone)