NP-MRD: Showing NP-Card for 5-methoxy-2-phenylchromen-4-one (NP0279973)

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Record Information

Version

2.0

Created at

2022-09-09 05:33:23 UTC

Updated at

2022-09-09 05:33:23 UTC

NP-MRD ID

NP0279973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methoxy-2-phenylchromen-4-one

Description

5-Methoxyflavone belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. 5-methoxy-2-phenylchromen-4-one is found in Imperata cylindrica. 5-methoxy-2-phenylchromen-4-one was first documented in 2019 (PMID: 31678783). Based on a literature review a small amount of articles have been published on 5-Methoxyflavone (PMID: 32534819) (PMID: 30445823).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.2147    0.3974   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6014   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403   -0.2194    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -1.2178    1.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072   -2.0260    1.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.8482    1.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.8488    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019   -0.6591    0.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.2622   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.3923   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -0.4580    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7907   -0.3748    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.5888   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5504    1.4628   -1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618    1.3315   -1.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765    1.0894   -0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0929    0.9503   -0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873    1.6983   -1.3418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5611   -0.0408    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7913    1.0709   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -0.6357   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5372    0.5650    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596   -1.3895    1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -2.7996    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -2.4638    2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606   -1.2104    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504   -1.0276    0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4248    0.6935   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062    2.2125   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5862    2.0251   -1.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6219    1.8782   -1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4  3  1  0
 15 10  1  0
  7 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 31  1  0
  6 25  1  0
  5 24  1  0
  4 23  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv1652309092207332D          

 19 21  0  0  0  0            999 V2000
    0.7145   -2.8875    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
    1.4289   -1.6500    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
    0.7145   -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
    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 O   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 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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
 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
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  9 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 19  2  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279973

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-10H,1H3

> <INCHI_KEY>
XRQSPUXANRGDAV-UHFFFAOYSA-N

> <FORMULA>
C16H12O3

> <MOLECULAR_WEIGHT>
252.269

> <EXACT_MASS>
252.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.718988362193876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2-phenyl-4H-chromen-4-one

> <JCHEM_LOGP>
2.809713832999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.176127915882173

> <JCHEM_PKA_STRONGEST_BASIC>
-4.762703996183261

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
73.4344

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-2-phenylchromen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    9   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₃

Average Mass

252.2690 Da

Monoisotopic Mass

252.07864 Da

IUPAC Name

5-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

5-methoxy-2-phenylchromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-10H,1H3

InChI Key

XRQSPUXANRGDAV-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

Species Name	Source	Reference
Imperata cylindrica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous ester
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen 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
logP	2.81	ChemAxon
pKa (Strongest Acidic)	15.18	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.43 m³·mol⁻¹	ChemAxon
Polarizability	26.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00004482

Chemspider ID

85301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-methylated flavonoid

METLIN ID

Not Available

PubChem Compound

94525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shanmugasundaram J, Subramanian V, Nadipelly J, Kathirvelu P, Sayeli V, Cheriyan BV: Anxiolytic-like activity of 5-methoxyflavone in mice with involvement of GABAergic and serotonergic systems - in vivo and in silico evidences. Eur Neuropsychopharmacol. 2020 Jul;36:100-110. doi: 10.1016/j.euroneuro.2020.05.009. Epub 2020 Jun 10. [PubMed:32534819 ]
Chen Z, Wang X, Xu Y, Wang C: Synthesis of (11)C-labeled DNA polymerase-beta inhibitor 5-methoxyflavone and PET/CT imaging thereof. Nucl Med Biol. 2019 Nov-Dec;78-79:17-22. doi: 10.1016/j.nucmedbio.2019.10.005. Epub 2019 Oct 23. [PubMed:31678783 ]
Lima JCS, de Oliveira RG, Silva VC, de Sousa PT Jr, Violante IMP, Macho A, Martins DTO: Anti-inflammatory activity of 4',6,7-trihydroxy-5-methoxyflavone from Fridericia chica (Bonpl.) L.G.Lohmann. Nat Prod Res. 2020 Mar;34(5):726-730. doi: 10.1080/14786419.2018.1495636. Epub 2018 Nov 16. [PubMed:30445823 ]
LOTUS database [Link]

Showing NP-Card for 5-methoxy-2-phenylchromen-4-one (NP0279973)

MOL for NP0279973 (5-methoxy-2-phenylchromen-4-one)

3D MOL for NP0279973 (5-methoxy-2-phenylchromen-4-one)

3D SDF for NP0279973 (5-methoxy-2-phenylchromen-4-one)

3D-SDF for NP0279973 (5-methoxy-2-phenylchromen-4-one)

PDB for NP0279973 (5-methoxy-2-phenylchromen-4-one)

3D PDB for NP0279973 (5-methoxy-2-phenylchromen-4-one)

SMILES for NP0279973 (5-methoxy-2-phenylchromen-4-one)

INCHI for NP0279973 (5-methoxy-2-phenylchromen-4-one)

Structure for NP0279973 (5-methoxy-2-phenylchromen-4-one)

3D Structure for NP0279973 (5-methoxy-2-phenylchromen-4-one)