NP-MRD: Showing NP-Card for 5,6,2'-Trimethoxyflavone (NP0052251)

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Record Information

Version

2.0

Created at

2022-04-27 23:22:37 UTC

Updated at

2022-04-27 23:22:37 UTC

NP-MRD ID

NP0052251

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,2'-Trimethoxyflavone

Description

2',5,6-Trimethoxyflavone belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 2',5,6-trimethoxyflavone is considered to be a flavonoid lipid molecule. 2',5,6-Trimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2',5,6-Trimethoxyflavone has been detected, but not quantified in, pomes. 5,6,2'-Trimethoxyflavone is found in Casimiroa edulis and Struthiola argentea. This could make 2',5,6-trimethoxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.3769    2.6792   -1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    1.6364   -0.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.9269    0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5665    1.2149    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2045    0.4934    2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4816   -0.5073    2.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.8359    2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -0.1024    1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -0.3948    0.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -1.3012    1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741   -1.5539    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303   -2.3708    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -0.8579   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675   -1.0433   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523   -1.9185   -0.0550 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171   -1.6439    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -0.3453   -1.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822   -0.6025   -2.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9591   -0.0774   -3.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    0.5438   -2.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8596    0.7577   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472    0.0532   -0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.2358   -0.2394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157    3.1783   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2706    2.2606   -1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7604    3.3734   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1618    1.9932    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136    0.7103    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623   -1.0765    3.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747   -1.6231    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -1.8498    2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147   -1.1142    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -2.6293    1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -1.0878    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -0.7054   -3.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189    0.9002   -2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    0.1443   -4.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669    1.0919   -3.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    1.4476   -2.2935 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 20 17  1  0
 17 18  1  0
 18 19  1  0
 17 14  2  0
 14 15  1  0
 15 16  1  0
  8  3  1  0
 23  9  1  0
 14 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 21 39  1  0
 20 38  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

  Mrv0541 05061309432D          

 23 25  0  0  0  0            999 V2000
    6.4302    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
    2.8579    2.4750    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
    6.4302   -1.2375    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
    6.4302   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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
    5.7158    0.0000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23 14  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052251

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-13-7-5-4-6-11(13)16-10-12(19)17-14(23-16)8-9-15(21-2)18(17)22-3/h4-10H,1-3H3

> <INCHI_KEY>
IQWXFMQSQNSHKI-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.43093538998397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dimethoxy-2-(2-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
2.494371301666667

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.533965474943663

> <JCHEM_PKA_STRONGEST_BASIC>
-4.376258929415804

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
86.36079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dimethoxy-2-(2-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -0.770   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -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  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8    9   14                                                       
CONECT    9    8   15                                                       
CONECT   10   12   16                                                       
CONECT   11    6   13   16                                                  
CONECT   12   10   17   19                                                  
CONECT   13    7   11   20                                                  
CONECT   14    8   17   23                                                  
CONECT   15    9   18   21                                                  
CONECT   16   10   11   23                                                  
CONECT   17   12   14   18                                                  
CONECT   18   15   17   22                                                  
CONECT   19   12                                                            
CONECT   20    1   13                                                       
CONECT   21    2   15                                                       
CONECT   22    3   18                                                       
CONECT   23   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
5,6,2'-Trimethoxyflavone	HMDB

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3166 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

5,6-dimethoxy-2-(2-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5,6-dimethoxy-2-(2-methoxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2OC

InChI Identifier

InChI=1S/C18H16O5/c1-20-13-7-5-4-6-11(13)16-10-12(19)17-14(23-16)8-9-15(21-2)18(17)22-3/h4-10H,1-3H3

InChI Key

IQWXFMQSQNSHKI-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
Casimiroa edulis	Plant	KNApSAcK
Struthiola argentea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

2p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110086 )

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	3.22	ALOGPS
logP	2.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	32.43 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

HMDB0037331

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016353

KNApSAcK ID

C00003813

Chemspider ID

22370322

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14484690

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,6,2'-Trimethoxyflavone (NP0052251)

MOL for NP0052251 (5,6,2'-Trimethoxyflavone)

3D MOL for NP0052251 (5,6,2'-Trimethoxyflavone)

3D SDF for NP0052251 (5,6,2'-Trimethoxyflavone)

3D-SDF for NP0052251 (5,6,2'-Trimethoxyflavone)

PDB for NP0052251 (5,6,2'-Trimethoxyflavone)

3D PDB for NP0052251 (5,6,2'-Trimethoxyflavone)

SMILES for NP0052251 (5,6,2'-Trimethoxyflavone)

INCHI for NP0052251 (5,6,2'-Trimethoxyflavone)

Structure for NP0052251 (5,6,2'-Trimethoxyflavone)

3D Structure for NP0052251 (5,6,2'-Trimethoxyflavone)