NP-MRD: Showing NP-Card for 6,2',4'-Trimethoxyflavone (NP0138325)

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Record Information

Version

1.0

Created at

2022-05-31 17:55:15 UTC

Updated at

2022-05-31 17:55:15 UTC

NP-MRD ID

NP0138325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,2',4'-Trimethoxyflavone

Description

6,2',4'-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. It was first documented in 2018 (PMID: 30305307). Based on a literature review a significant number of articles have been published on 6,2',4'-trimethoxyflavone (PMID: 34622690) (PMID: 31606043) (PMID: 31505164) (PMID: 31238104).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -6.4189   -0.5387    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818   -0.7718    1.8790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048   -0.5660    1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950   -0.7904    2.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405   -0.5835    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.1409    0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0502    0.0420   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.4640   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    0.6331   -1.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    1.0178   -2.8257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    0.3369   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540    0.4778   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9092    0.2007   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2458    0.3545   -0.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2718    0.0692    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5128   -0.2282    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743   -0.3676    1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -0.0862    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332   -0.2196    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213    0.0742   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3933    0.5080   -1.7114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5442    0.7276   -2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8115   -0.1362    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3089   -0.9819    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5894    0.5482    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397   -0.9507    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -1.1325    3.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -0.7756    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3824    0.6947   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.8201   -2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1493    0.8287    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1494   -0.9649    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2688    0.2313    0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2641   -0.4519    1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649   -0.7087    2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659    1.5212   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2537    1.0159   -3.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -0.2199   -2.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6530    0.0495   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 12  2  0
  4  3  1  0
 19  7  1  0
 12 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 39  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
  5 28  1  0
  4 27  1  0
  8 29  1  0
 17 35  1  0
 16 34  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 12 30  1  0
M  END


  Mrv1652305312219552D          

 23 25  0  0  0  0            999 V2000
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   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
   -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 O   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
   -1.4289    0.0000    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
   -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
    0.0000   -1.6500    0.0000 C   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
    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
    0.0000   -0.0000    0.0000 O   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
    2.1434   -0.4125    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
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    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
  3 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 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
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C=C1)C1=CC(=O)C2=C(O1)C=CC(OC)=C2

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

> <INCHI_KEY>
WUWFDVDASNSUKP-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.771354054280735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

> <JCHEM_LOGP>
2.494371301666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.155552335290775

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325622731293251

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
86.36080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(2,4-dimethoxyphenyl)-6-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   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  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    3                                                       
CONECT   11    8   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

720675-74-1

SMILES

COC1=CC(OC)=C(C=C1)C1=CC(=O)C2=C(O1)C=CC(OC)=C2

InChI Identifier

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

InChI Key

WUWFDVDASNSUKP-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

Not Available

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
4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
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

Not Available

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

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

600202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688802

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren R, Lu Q, Sherchan P, Fang Y, Lenahan C, Tang L, Huang Y, Liu R, Zhang JH, Zhang J, Tang J: Inhibition of Aryl Hydrocarbon Receptor Attenuates Hyperglycemia-Induced Hematoma Expansion in an Intracerebral Hemorrhage Mouse Model. J Am Heart Assoc. 2021 Oct 19;10(20):e022701. doi: 10.1161/JAHA.121.022701. Epub 2021 Oct 8. [PubMed:34622690 ]
Chen WC, Chang LH, Huang SS, Huang YJ, Chih CL, Kuo HC, Lee YH, Lee IH: Aryl hydrocarbon receptor modulates stroke-induced astrogliosis and neurogenesis in the adult mouse brain. J Neuroinflammation. 2019 Oct 12;16(1):187. doi: 10.1186/s12974-019-1572-7. [PubMed:31606043 ]
Scobie MR, Houke HR, Rice CD: Modulation of glioma-inflammation crosstalk profiles in human glioblastoma cells by indirubin-3'-(2,3 dihydroxypropyl)-oximether (E804) and 7-bromoindirubin-3'-oxime (7BIO). Chem Biol Interact. 2019 Oct 1;312:108816. doi: 10.1016/j.cbi.2019.108816. Epub 2019 Sep 7. [PubMed:31505164 ]
Apaza T L, Serban AM, Cabanillas AH, Villacampa A, Rumbero A: Flavonoids of Tripodanthus acutifolius inhibit TNF-alpha production in LPS-activated THP-1 and B16-F10cells. J Ethnopharmacol. 2019 Oct 5;242:112036. doi: 10.1016/j.jep.2019.112036. Epub 2019 Jun 22. [PubMed:31238104 ]
Authors unspecified: Correction to "Antagonism of Aryl Hydrocarbon Receptor Signaling by 6, 2',4'-Trimethoxyflavone". J Pharmacol Exp Ther. 2018 Nov;367(2):291. doi: 10.1124/jpet.109.158261err. [PubMed:30305307 ]

Showing NP-Card for 6,2',4'-Trimethoxyflavone (NP0138325)

MOL for NP0138325 (6,2',4'-Trimethoxyflavone)

3D MOL for NP0138325 (6,2',4'-Trimethoxyflavone)

3D SDF for NP0138325 (6,2',4'-Trimethoxyflavone)

3D-SDF for NP0138325 (6,2',4'-Trimethoxyflavone)

PDB for NP0138325 (6,2',4'-Trimethoxyflavone)

3D PDB for NP0138325 (6,2',4'-Trimethoxyflavone)

SMILES for NP0138325 (6,2',4'-Trimethoxyflavone)

INCHI for NP0138325 (6,2',4'-Trimethoxyflavone)

Structure for NP0138325 (6,2',4'-Trimethoxyflavone)

3D Structure for NP0138325 (6,2',4'-Trimethoxyflavone)