NP-MRD: Showing NP-Card for Luteolin 7-methyl ether (NP0048728)

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Record Information

Version

2.0

Created at

2022-03-17 21:01:15 UTC

Updated at

2022-03-17 21:01:15 UTC

NP-MRD ID

NP0048728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolin 7-methyl ether

Description

Luteolin 7-methyl ether, also known as 7-O-methylluteolin, 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, luteolin 7-methyl ether is considered to be a flavonoid lipid molecule. Luteolin 7-methyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Luteolin 7-methyl ether has been detected, but not quantified in, a few different foods, such as common sages, herbs and spices, and tea. Luteolin 7-methyl ether is found in Adenothamnus validus, Antirrhinum spp., Aquilaria sinensis, Arnica longifolia, Artemisia annua, Artemisia barrelieri, Artemisia molinieri, Blumea balsamifera, Cistus laurifolius, Cyperus conglomeratus, Daphne genkwa, Daphne laureola, Daphne sericea, Dubautia arborea, Eucryphia jinksii, Eucryphia lucida, Gochnatia argentina, Hazardia squarrosa var. grindelioides, Heliotropium stenophyllum, Heteromera fuscata, Hintonia latiflora, Holocarpha virgata, Isocoma acradenia, Isodon eriocalyx, Nonea lutea, Nonea pulla, Notholaena californica, Origanum calcaratum, Origanum dictamnus , Origanum floribundum, Origanum majorana , Origanum microphyllum, Origanum onites , Origanum syriacum , Origanum vulgare subsp. Glandulosum , Origanum vulgare subsp. Hirtum , Petunia parviflora, Salpiglossis sinuata, Salvia euphratica, Salvia hypoleuca, Salvia lavandulaefolia, Salvia limbata, Salvia moorcroftiana , Salvia sclarea , Sideritis spp., Sorghum durra, Teucrium marum , Thymus membranaceus, Verbascum lychnitis and Wunderlichia crulsiana. This could make luteolin 7-methyl ether a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309432D          

 22 24  0  0  0  0            999 V2000
    0.0000    0.0000    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   -1.6500    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
    1.4289    0.8250    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
    4.2868    0.8250    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -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
    3.5724    1.2375    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
    2.8579    0.0000    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
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  6  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 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048728

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-7,17-19H,1H3

> <INCHI_KEY>
RRRSSAVLTCVNIQ-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.804855900068482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.5490178679999995

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.941325463813527

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.327973213765677

> <JCHEM_PKA_STRONGEST_BASIC>
-4.745761850055501

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
79.37710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin 7-methyl ether

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    8   11                                                       
CONECT    5    9   12                                                       
CONECT    6    9   15                                                       
CONECT    7   13   14                                                       
CONECT    8    2    4   14                                                  
CONECT    9    5    6   21                                                  
CONECT   10    3   11   17                                                  
CONECT   11    4   10   18                                                  
CONECT   12    5   16   19                                                  
CONECT   13    7   16   20                                                  
CONECT   14    7    8   22                                                  
CONECT   15    6   16   22                                                  
CONECT   16   12   13   15                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1    9                                                       
CONECT   22   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
5,3',4'-Trihydroxy-7-methoxyflavone	HMDB
7-O-Methylluteolin	HMDB
Hydroxygenkwanin	MeSH

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

luteolin 7-methyl ether

CAS Registry Number

20243-59-8

SMILES

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

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-7,17-19H,1H3

InChI Key

RRRSSAVLTCVNIQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenothamnus validus	Plant	KNApSAcK
Antirrhinum spp.	Plant	KNApSAcK
Aquilaria sinensis	LOTUS Database	35616633
Arnica longifolia	Plant	KNApSAcK
Artemisia annua	LOTUS Database	35616633
Artemisia barrelieri	Plant	KNApSAcK
Artemisia molinieri	LOTUS Database	35616633
Blumea balsamifera	LOTUS Database	35616633
Cistus laurifolius	LOTUS Database	35616633
Cyperus conglomeratus	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633
Daphne laureola	LOTUS Database	35616633
Daphne sericea	Plant	KNApSAcK
Dubautia arborea	Plant	KNApSAcK
Eucryphia jinksii	Plant	KNApSAcK
Eucryphia lucida	Plant	KNApSAcK
Gochnatia argentina	LOTUS Database	35616633
Hazardia squarrosa var. grindelioides	Plant	KNApSAcK
Heliotropium stenophyllum	Plant	KNApSAcK
Heteromera fuscata	LOTUS Database	35616633
Hintonia latiflora	LOTUS Database	35616633
Holocarpha virgata	LOTUS Database	35616633
Isocoma acradenia	LOTUS Database	35616633
Isodon eriocalyx	LOTUS Database	35616633
Nonea lutea	Plant	KNApSAcK
Nonea pulla	Plant	KNApSAcK
Notholaena californica	Plant	KNApSAcK
Origanum calcaratum	Plant	KNApSAcK
Origanum dictamnus	Plant	KNApSAcK
Origanum floribundum	Plant	KNApSAcK
Origanum majorana	Plant	KNApSAcK
Origanum microphyllum	Plant	KNApSAcK
Origanum onites	Plant	KNApSAcK
Origanum syriacum	Plant	KNApSAcK
Origanum vulgare subsp. Glandulosum	Plant	KNApSAcK
Origanum vulgare subsp. Hirtum	Plant	KNApSAcK
Petunia parviflora	Plant	KNApSAcK
Salpiglossis sinuata	LOTUS Database	35616633
Salvia euphratica	Plant	KNApSAcK
Salvia hypoleuca	Plant	KNApSAcK
Salvia lavandulaefolia	Plant	KNApSAcK
Salvia limbata	LOTUS Database	35616633
Salvia moorcroftiana	Plant	KNApSAcK
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia sclarea	Plant	KNApSAcK
Sideritis spp.	Plant	KNApSAcK
Sorghum durra	Plant	KNApSAcK
Teucrium marum	Plant	KNApSAcK
Thymus membranaceus	Plant	KNApSAcK
Verbascum lychnitis	LOTUS Database	35616633
Wunderlichia crulsiana	Plant	KNApSAcK

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111045 )

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	3.08	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.33	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	29.8 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

HMDB0037339

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016361

KNApSAcK ID

C00003865

Chemspider ID

4476827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Luteolin 7-methyl ether (NP0048728)

MOL for NP0048728 (Luteolin 7-methyl ether)

3D MOL for NP0048728 (Luteolin 7-methyl ether)

3D SDF for NP0048728 (Luteolin 7-methyl ether)

3D-SDF for NP0048728 (Luteolin 7-methyl ether)

PDB for NP0048728 (Luteolin 7-methyl ether)

3D PDB for NP0048728 (Luteolin 7-methyl ether)

SMILES for NP0048728 (Luteolin 7-methyl ether)

INCHI for NP0048728 (Luteolin 7-methyl ether)

Structure for NP0048728 (Luteolin 7-methyl ether)

3D Structure for NP0048728 (Luteolin 7-methyl ether)