NP-MRD: Showing NP-Card for 3,4',5,7-Tetrahydroxy-6-methoxyflavone (NP0045935)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:39 UTC

Updated at

2022-03-17 19:45:39 UTC

NP-MRD ID

NP0045935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4',5,7-Tetrahydroxy-6-methoxyflavone

Description

3,4',5,7-Tetrahydroxy-6-methoxyflavone, also known as 6-methoxykaempferol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 3,4',5,7-tetrahydroxy-6-methoxyflavone is considered to be a flavonoid lipid molecule. 3,4',5,7-Tetrahydroxy-6-methoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,4',5,7-Tetrahydroxy-6-methoxyflavone has been detected, but not quantified in, several different foods, such as fruits, german camomiles, safflowers, and sweet cherries. 3,4',5,7-Tetrahydroxy-6-methoxyflavone is found in Actinocephalus ramosus, Adenostoma sparsifolium, Aeonium spp., Ageratina espinosara, Ageratina havanensis, Ageratina saltillensis, Agnorhiza elata, Ambrosia artemisiifolia, Ambrosia artemisioides, Arctotis argentea, Arnica chamissonis, Arnica nevadensis, Artemisia alba, Baccharis vaccinioides, Balsamorhiza sagittata, Betula maximowicziana, Bletilla formosana, Brickellia vernicosa, Calycera eryngioides, Centaurea incana, Chrysactinia mexicana, Eriodictyon trichocalyx, Eupatorium altissimum, Eupatorium areolare, Ageratina altissima, Eupatorium serotinum, Heteranthemis viscidehirta, Heterotheca grandiflora, Ligularia amplexicaulis, Matricaria chamomilla , Paepalanthus denudatus, Paepalanthus hilairei, Paepalanthus ramosus, Passiflora palmeri, Rhaponticum carthamoides , Tagetes patula and Xanthium strumarium . This could make 3,4',5,7-tetrahydroxy-6-methoxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305202D          

 23 25  0  0  0  0            999 V2000
   -2.1434   -1.2375    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
    2.8579    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
    3.5724    1.2375    0.0000 C   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
    2.8579    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
   -0.7145   -0.4125    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
    0.7145   -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
    0.0000   -1.6500    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
    2.1434   -0.4125    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
    5.0013    1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  1  1  0  0  0  0
 22 16  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-16-9(18)6-10-11(13(16)20)12(19)14(21)15(23-10)7-2-4-8(17)5-3-7/h2-6,17-18,20-21H,1H3

> <INCHI_KEY>
OGQSUSFDBWGFFJ-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.2623

> <EXACT_MASS>
316.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.559538271942507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.30219352

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.415795170865358

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.950428482734611

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9508999166167973

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
81.34450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methoxykaempferol

> <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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    2    3   15                                                  
CONECT    8    4    5   17                                                  
CONECT    9    6   16   18                                                  
CONECT   10    6   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   14   19                                                  
CONECT   13   11   16   20                                                  
CONECT   14   12   15   21                                                  
CONECT   15    7   14   23                                                  
CONECT   16    9   13   22                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    1   16                                                       
CONECT   23   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
6-Methoxykaempferol	HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
4',5,7-Trihydroxy-6-methoxyflavonol	HMDB
3,5,7,4'-Tetrahydroxy-6-methoxyflavone	HMDB

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2623 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

Traditional Name

6-methoxykaempferol

CAS Registry Number

32520-55-1

SMILES

COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C16H12O7/c1-22-16-9(18)6-10-11(13(16)20)12(19)14(21)15(23-10)7-2-4-8(17)5-3-7/h2-6,17-18,20-21H,1H3

InChI Key

OGQSUSFDBWGFFJ-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
Actinocephalus ramosus	LOTUS Database	35616633
Adenostoma sparsifolium	Plant	KNApSAcK
Aeonium spp.	Plant	KNApSAcK
Ageratina espinosara	Plant	KNApSAcK
Ageratina havanensis	Plant	KNApSAcK
Ageratina saltillensis	LOTUS Database	35616633
Agnorhiza elata	LOTUS Database	35616633
Ambrosia artemisiifolia	Plant	KNApSAcK
Ambrosia artemisioides	LOTUS Database	35616633
Arctotis argentea	LOTUS Database	35616633
Arnica chamissonis	LOTUS Database	35616633
Arnica nevadensis	LOTUS Database	35616633
Artemisia alba	LOTUS Database	35616633
Baccharis vaccinioides	Plant	KNApSAcK
Balsamorhiza sagittata	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Bletilla formosana	Plant	KNApSAcK
Brickellia vernicosa	LOTUS Database	35616633
Calycera eryngioides	LOTUS Database	35616633
Carthamus tinctorius	FooDB	KNAPSACK
Centaurea incana	Plant	KNApSAcK
Chrysactinia mexicana	Plant	KNApSAcK
Eriodictyon trichocalyx	Plant	KNApSAcK
Eupatorium altissimum	Plant	KNApSAcK
Eupatorium areolare	Plant	KNApSAcK
Eupatorium rugosum	LOTUS Database	35616633
Eupatorium serotinum	Plant	KNApSAcK
Heteranthemis viscidehirta	Plant	KNApSAcK
Heterotheca grandiflora	Plant	KNApSAcK
Ligularia amplexicaulis	LOTUS Database	35616633
Matricaria chamomilla	Plant	KNApSAcK
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Paepalanthus denudatus	Plant	KNApSAcK
Paepalanthus hilairei	Plant	KNApSAcK
Paepalanthus ramosus	Plant	KNApSAcK
Passiflora palmeri	LOTUS Database	35616633
Prunus avium	FooDB	KNAPSACK
Rhaponticum carthamoides	Plant	KNApSAcK
Tagetes patula	LOTUS Database	35616633
Xanthium strumarium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112864 )

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	1.95	ALOGPS
logP	2.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.95	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.56 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

HMDB0030547

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002421

KNApSAcK ID

C00004593

Chemspider ID

4526882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377945

PDB ID

Not Available

ChEBI ID

563477

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4',5,7-Tetrahydroxy-6-methoxyflavone (NP0045935)

MOL for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

3D MOL for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

3D SDF for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

3D-SDF for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

PDB for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

3D PDB for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

SMILES for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

INCHI for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

Structure for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)

3D Structure for NP0045935 (3,4',5,7-Tetrahydroxy-6-methoxyflavone)