NP-MRD: Showing NP-Card for 3-Methylgalangin (NP0052833)

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Record Information

Version

2.0

Created at

2022-04-27 23:44:57 UTC

Updated at

2022-04-27 23:44:57 UTC

NP-MRD ID

NP0052833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Methylgalangin

Description

5,7-Dihydroxy-3-methoxyflavone, also known as galangin 3-methyl ether or 3-methylgalangin, belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-3-methoxyflavone is considered to be a flavonoid lipid molecule. 5,7-Dihydroxy-3-methoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5,7-Dihydroxy-3-methoxyflavone is found, on average, in the highest concentration within mexican oregano. 5,7-Dihydroxy-3-methoxyflavone has also been detected, but not quantified in, herbs and spices. This could make 5,7-dihydroxy-3-methoxyflavone a potential biomarker for the consumption of these foods. 3-Methylgalangin is found in Achyrocline alata, Achyrocline flaccida, Achyrocline satureioides, Alnus alnobetula, Alpinia officinarum, Anaphalis margaritacea, Andromeda polifolia, Cheilanthes kaulfussii, Eremophila alternifolia , Eremophila racemosissima, Gaga kaulfussii, Helichrysum armenium, Helichrysum aureum, Helichrysum graveolen, Helichrysum italicum, Helichrysum picardii, Helichrysum platypterum, Heliotropium filifolium, Heliotropium huascoense, Heliotropium huascuense, Heliotropium megalanthum, Heliotropium pycnophyllum, Heliotropium sinuatum, Heliotropium stenophyllum, Heliotropium taltalense, Lippia graveolens, Lychnophora markgravii, Muntingia calabura, Nothofagus spp., Notholaena candida, Ozothamnus spp., Pentagramma triangularis, Populus nigra , Pseudognaphalium cheiranthifolium, Pseudognaphalium montevidense and Woodsia scopulina. A monomethoxyflavone that is galangin in which the hydroxy group at position 3 has been replaced by a methoxy group.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.5590   -2.8793    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647   -2.2788   -0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231   -1.2803   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665    0.0345   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.5553   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.9158    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3559    2.4967    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4896    1.7517    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    0.4150   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0630   -0.1497   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263    0.9549   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785    0.6399   -0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845    1.6978   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357    1.4486   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8605    2.5134   -0.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328    0.1483   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475   -0.9443   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213   -2.2170   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -0.6680   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.6256   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -2.8263   -0.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -2.9676    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -2.1603    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -3.8671    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    2.5280    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4778    3.5458    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    2.2027    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2241   -0.1909   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0355   -1.1781   -0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294    2.7240   -0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883    2.8505   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835   -0.0908   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -3.0989   -0.4270 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 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  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
 20  3  1  0
 10  5  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
M  END


  Mrv0541 02241215142D          

 21 23  0  0  0  0            999 V2000
    1.7733    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.4745    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
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  2  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  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052833

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

> <INCHI_KEY>
LYISDADPVOHJBJ-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.43803415467274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
2.8762574966666667

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.113460799187116

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.442987877179501

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8747114784658585

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.65160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galangin 3-methyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.310   2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.078   1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.692   2.309   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.692   3.849   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.078   4.619   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.696   0.001   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.692   0.001   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.692   1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.078   2.309   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.078   3.849   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.310   4.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.696   3.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.696   2.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.310   1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.310  -2.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.310  -0.769   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.078   0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.692  -0.769   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.692  -2.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.078  -3.079   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.078  -4.619   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6   16                                                            
CONECT    7    8   18                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15   16   20                                                       
CONECT   16    6   15   17                                                  
CONECT   17    2   16   18                                                  
CONECT   18    7   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Galangin 3-methyl ether	ChEBI
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-1-benzopyran-4-one	Kegg
3-Methylgalangin	HMDB
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one	HMDB
5,7-Dihydroxy-3-methoxyflavone	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

5,7-dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

galangin 3-methyl ether

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

InChI Key

LYISDADPVOHJBJ-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
Achyrocline alata	LOTUS Database	35616633
Achyrocline flaccida	Plant	KNApSAcK
Achyrocline satureioides	LOTUS Database	35616633
Alnus viridis	LOTUS Database	35616633
Alpinia officinarum	LOTUS Database	35616633
Anaphalis margaritacea	LOTUS Database	35616633
Andromeda polifolia	Plant	KNApSAcK
Cheilanthes kaulfussii	Plant	KNApSAcK
Eremophila alternifolia	Plant	KNApSAcK
Eremophila racemosissima	Plant	KNApSAcK
Gaga kaulfussii	LOTUS Database	35616633
Helichrysum armenium	LOTUS Database	35616633
Helichrysum aureum	Plant	KNApSAcK
Helichrysum graveolen	Plant	KNApSAcK
Helichrysum italicum	LOTUS Database	35616633
Helichrysum picardii	Plant	KNApSAcK
Helichrysum platypterum	LOTUS Database	35616633
Heliotropium filifolium	Plant	KNApSAcK
Heliotropium huascoense	Plant	KNApSAcK
Heliotropium huascuense	Plant	KNApSAcK
Heliotropium megalanthum	Plant	KNApSAcK
Heliotropium pycnophyllum	Plant	KNApSAcK
Heliotropium sinuatum	Plant	KNApSAcK
Heliotropium stenophyllum	Plant	KNApSAcK
Heliotropium taltalense	LOTUS Database	35616633
Lippia graveolens	LOTUS Database	35616633
Lychnophora markgravii	Plant	KNApSAcK
Muntingia calabura	LOTUS Database	35616633
Nothofagus spp.	Plant	KNApSAcK
Notholaena candida	Plant	KNApSAcK
Ozothamnus spp.	Plant	KNApSAcK
Pentagramma triangularis	LOTUS Database	35616633
Populus nigra	Plant	KNApSAcK
Pseudognaphalium cheiranthifolium	Plant	KNApSAcK
Pseudognaphalium montevidense	LOTUS Database	35616633
Woodsia scopulina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:1602 )
monomethoxyflavone (CHEBI:1602 )
flavonols (C11577 )
Flavones and Flavonols (LMPK12111654 )

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	3.49	ALOGPS
logP	2.88	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.65 m³·mol⁻¹	ChemAxon
Polarizability	28.44 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