NP-MRD: Showing NP-Card for 4',5,7-Trimethylapigenin (NP0046045)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:29 UTC

Updated at

2022-03-17 19:47:29 UTC

NP-MRD ID

NP0046045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4',5,7-Trimethylapigenin

Description

4',5,7-Trimethylapigenin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4',5,7-trimethylapigenin is considered to be a flavonoid lipid molecule. 4',5,7-Trimethylapigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',5,7-Trimethylapigenin has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges. 4',5,7-Trimethylapigenin is found in Boesenbergia pandurata , Boesenbergia rotunda, Citrus aurantium , Citrus grandis var.tomentosa , Citrus hassaku, Citrus grandis , Garcinia kola , Gonocaryum calleryanum, Kaempferia parviflora , Orthosiphon spicatus, Piper cubeba, Piper porphyrophyllum, Streptomyces avermitilis and Tanacetum vulgare. This could make 4',5,7-trimethylapigenin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304072020302D          

 23 25  0  0  0  0            999 V2000
    7.8592    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0625    0.0000 C   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
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1

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

> <INCHI_KEY>
ZXJJBDHPUHUUHD-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.02673171392914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
2.494371301666667

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.54287180294915

> <JCHEM_PKA_STRONGEST_BASIC>
-4.343671577856831

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
86.36079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-APR-20         0                                  
HETATM    1  C   UNK     0      14.671   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.850   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6   11   12                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9    2    3   14                                                  
CONECT   10    4    5   19                                                  
CONECT   11    6    7   20                                                  
CONECT   12    6   16   17                                                  
CONECT   13    8   16   18                                                  
CONECT   14    8    9   21                                                  
CONECT   15    7   16   21                                                  
CONECT   16   12   13   15                                                  
CONECT   17   12   23                                                       
CONECT   18   13                                                            
CONECT   19    1   10                                                       
CONECT   20   11   22                                                       
CONECT   21   14   15                                                       
CONECT   22   20                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
4'57-Trimethoxyflavone	ChEMBL, HMDB
4',5,7-Trimethoxy-flavone	HMDB
4',5,7-Trimethyl-apigenin	HMDB, MeSH
5,7,4'-Trimethoxyflavone	HMDB
5,7,4'-Trimethylapigenin	HMDB, MeSH
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzenopyran-4-one	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
6-Hydroxy-4',5,7-trimethoxyflavone	HMDB
Apigenin 5,7,4'-trimethyl ether	HMDB
Apigenin trimethyl ether	HMDB
4',5,7-Trimethoxyflavone	MeSH
4’,5,7-Trimethoxyflavone	HMDB
5,7,4'-Tri-O-methylapigenin	HMDB
5,7,4'-Trimethoxyapigenin	HMDB
5,7,4’-Tri-O-methylapigenin	HMDB
5,7,4’-Trimethoxyapigenin	HMDB
5,7,4’-Trimethoxyflavone	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)chromone	HMDB
5,7-Dimethoxy-4-oxo-2-(4-methoxyphenyl)-4H-1-benzopyran	HMDB
Tri-O-methylapigenin	HMDB
Trimethylapigenin	HMDB

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3166 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

5631-70-9

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1

InChI Identifier

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

InChI Key

ZXJJBDHPUHUUHD-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
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Citrus aurantium	Plant	KNApSAcK
Citrus grandis var.tomentosa	Plant	KNApSAcK
Citrus hassaku	LOTUS Database	35616633
Citrus maxima	Plant	KNApSAcK
Citrus reticulata	FooDB	KNAPSACK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Garcinia kola	Plant	KNApSAcK
Gonocaryum calleryanum	LOTUS Database	35616633
Kaempferia parviflora	Plant	KNApSAcK
Orthosiphon spicatus	Plant	KNApSAcK
Piper cubeba	LOTUS Database	35616633
Piper porphyrophyllum	LOTUS Database	35616633
Streptomyces avermitilis	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-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 (LMPK12111071 )

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	3.21	ALOGPS
logP	2.49	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	15.54	ChemAxon
pKa (Strongest Basic)	-4.3	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	33.03 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

HMDB0030842

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002800

KNApSAcK ID

Not Available

Chemspider ID

72029

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

79730

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4',5,7-Trimethylapigenin (NP0046045)

MOL for NP0046045 (4',5,7-Trimethylapigenin)

3D MOL for NP0046045 (4',5,7-Trimethylapigenin)

3D SDF for NP0046045 (4',5,7-Trimethylapigenin)

3D-SDF for NP0046045 (4',5,7-Trimethylapigenin)

PDB for NP0046045 (4',5,7-Trimethylapigenin)

3D PDB for NP0046045 (4',5,7-Trimethylapigenin)

SMILES for NP0046045 (4',5,7-Trimethylapigenin)

INCHI for NP0046045 (4',5,7-Trimethylapigenin)

Structure for NP0046045 (4',5,7-Trimethylapigenin)

3D Structure for NP0046045 (4',5,7-Trimethylapigenin)