NP-MRD: Showing NP-Card for 7,8,4'-Trimethylisoscutellarein (NP0048802)

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Record Information

Version

2.0

Created at

2022-03-17 21:02:25 UTC

Updated at

2022-03-17 21:02:25 UTC

NP-MRD ID

NP0048802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8,4'-Trimethylisoscutellarein

Description

5-Hydroxy-4',7,8-trimethoxyflavone, also known as isoscutellarein 7,8,4'-trimethyl ether, belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 5-hydroxy-4',7,8-trimethoxyflavone is considered to be a flavonoid lipid molecule. 5-Hydroxy-4',7,8-trimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5-Hydroxy-4',7,8-trimethoxyflavone has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). 7,8,4'-Trimethylisoscutellarein is found in Asterella blumeana, Calceolaria irazeunsis, Calceolaria spp., Peperomia blanda and Peperomia sui. This could make 5-hydroxy-4',7,8-trimethoxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219312D          

 24 26  0  0  0  0            999 V2000
   -0.3568   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  2  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)14-8-12(19)16-13(20)9-15(22-2)17(23-3)18(16)24-14/h4-9,20H,1-3H3

> <INCHI_KEY>
RRZRJBICWWNHRB-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.746972429048654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.84080598

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18772604889555

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.080451106285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.385599865757411

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
88.3417

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.666  -1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.333   1.925   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.333   3.465   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.335  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.667  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.335  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.666  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.666   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.666   1.925   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.666   3.465   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.002  -3.465   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.333  -2.695   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.333  -1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.667  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.667   1.155   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.002  -1.155   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.334  -0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.334  -2.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.667  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12    1   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15   14                                                            
CONECT   16    8   23                                                       
CONECT   17   18   24                                                       
CONECT   18    2   17   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20    4   19                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-7,8,4'-trimethoxyflavone	HMDB
5-Hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
Isoscutellarein 7,8,4'-trimethyl ether	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3160 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

57096-03-4

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2O

InChI Identifier

InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)14-8-12(19)16-13(20)9-15(22-2)17(23-3)18(16)24-14/h4-9,20H,1-3H3

InChI Key

RRZRJBICWWNHRB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Asterella blumeana	Plant	KNApSAcK
Calceolaria irazeunsis	Plant	KNApSAcK
Calceolaria spp.	Plant	KNApSAcK
Citrus reticulata	FooDB	KNAPSACK
Peperomia blanda	Plant	KNApSAcK
Peperomia sui	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111367 )

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	3.31	ALOGPS
logP	2.84	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.34 m³·mol⁻¹	ChemAxon
Polarizability	33.75 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

HMDB0037458

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016520

KNApSAcK ID

C00003854

Chemspider ID

10405466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7,8,4'-Trimethylisoscutellarein (NP0048802)

MOL for NP0048802 (7,8,4'-Trimethylisoscutellarein)

3D MOL for NP0048802 (7,8,4'-Trimethylisoscutellarein)

3D SDF for NP0048802 (7,8,4'-Trimethylisoscutellarein)

3D-SDF for NP0048802 (7,8,4'-Trimethylisoscutellarein)

PDB for NP0048802 (7,8,4'-Trimethylisoscutellarein)

3D PDB for NP0048802 (7,8,4'-Trimethylisoscutellarein)

SMILES for NP0048802 (7,8,4'-Trimethylisoscutellarein)

INCHI for NP0048802 (7,8,4'-Trimethylisoscutellarein)

Structure for NP0048802 (7,8,4'-Trimethylisoscutellarein)

3D Structure for NP0048802 (7,8,4'-Trimethylisoscutellarein)