NP-MRD: Showing NP-Card for Sinensetin (NP0048557)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:20 UTC

Updated at

2022-03-17 20:58:20 UTC

NP-MRD ID

NP0048557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinensetin

Description

Sinensetin 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, sinensetin is considered to be a flavonoid lipid molecule. Sinensetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sinensetin is a bitter tasting compound. Outside of the human body, Sinensetin is found, on average, in the highest concentration within sweet oranges. Sinensetin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits, mandarin orange (clementine, tangerine), and rosemaries. This could make sinensetin a potential biomarker for the consumption of these foods. Sinensetin is found in Ageratina conyzoides, Ageratum conyzoides , Bauhinia championii , Chenopodium botrys , Chenopodium championii, Chromolaena odorata , Citrus auranthium, Citrus aurantium , Citrus grandis var.tomentosa , Citrus hassaku, Citrus japonica, Citrus kinokuni, Citrus leiocarpa, Citrus maxima, Citrus sinensis, Citrus tangerina , Citrus tankan, Clerodendranthus spicatus, Conoclinium coelestinum, Kickxia spuria, Murraya exotica, Murraya paniculata , Orthosiphon aristatus , Orthosiphon spicatus and Orthosiphon stamineus . Sinensetin was first documented in 2013 (PMID: 22438091). A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3' and 4' respectively (PMID: 25735898).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309152D          

 27 29  0  0  0  0            999 V2000
   -2.8579    0.8250    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
    5.0013   -0.4125    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
    3.5724   -2.8875    0.0000 C   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
   -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
    0.7145   -1.2375    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
    0.0000    0.0000    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
   -1.4289    0.8250    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
    3.5724   -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
    2.8579   -1.6500    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
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 12  2  0  0  0  0
 22  1  1  0  0  0  0
 22 13  1  0  0  0  0
 23  2  1  0  0  0  0
 23 15  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 19  1  0  0  0  0
 26  5  1  0  0  0  0
 26 20  1  0  0  0  0
 27 14  1  0  0  0  0
 27 16  1  0  0  0  0
M  END

  Mrv0541 05061309152D          

 27 29  0  0  0  0            999 V2000
   -2.8579    0.8250    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
    5.0013   -0.4125    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
    3.5724   -2.8875    0.0000 C   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
   -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
    0.7145   -1.2375    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
    0.0000    0.0000    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
   -1.4289    0.8250    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
    3.5724   -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
    2.8579   -1.6500    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
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 12  2  0  0  0  0
 22  1  1  0  0  0  0
 22 13  1  0  0  0  0
 23  2  1  0  0  0  0
 23 15  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 19  1  0  0  0  0
 26  5  1  0  0  0  0
 26 20  1  0  0  0  0
 27 14  1  0  0  0  0
 27 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048557

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

> <INCHI_KEY>
LKMNXYDUQXAUCZ-UHFFFAOYSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.3686

> <EXACT_MASS>
372.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.958046318752324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.1790287703333333

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.277344377109781

> <JCHEM_PKA_STRONGEST_BASIC>
-4.199966154848695

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
99.28719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinensetin

> <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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   11   15                                                       
CONECT    9   12   14                                                       
CONECT   10   16   17                                                       
CONECT   11    6    8   14                                                  
CONECT   12    9   18   21                                                  
CONECT   13    7   15   22                                                  
CONECT   14    9   11   27                                                  
CONECT   15    8   13   23                                                  
CONECT   16   10   18   27                                                  
CONECT   17   10   19   24                                                  
CONECT   18   12   16   20                                                  
CONECT   19   17   20   25                                                  
CONECT   20   18   19   26                                                  
CONECT   21   12                                                            
CONECT   22    1   13                                                       
CONECT   23    2   15                                                       
CONECT   24    3   17                                                       
CONECT   25    4   19                                                       
CONECT   26    5   20                                                       
CONECT   27   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
5,6,7,3',4'-Pentamethoxyflavone	ChEBI
Pedalitin permethyl ether	ChEBI
2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one	HMDB
2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one	HMDB
3',4',5,6,7-Pentamethoxyflavone	HMDB

Chemical Formula

C₂₀H₂₀O₇

Average Mass

372.3686 Da

Monoisotopic Mass

372.12090 Da

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one

Traditional Name

sinensetin

CAS Registry Number

2306-27-6

SMILES

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

InChI Identifier

InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

InChI Key

LKMNXYDUQXAUCZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina conyzoides	Plant	KNApSAcK
Ageratum conyzoides	Plant	KNApSAcK
Bauhinia championii	Plant	KNApSAcK
Chenopodium botrys	Plant	KNApSAcK
Chenopodium championii	Plant	KNApSAcK
Chromolaena odorata	Plant	KNApSAcK
Citrus auranthium	Plant	KNApSAcK
Citrus aurantium	Plant	KNApSAcK
Citrus grandis var.tomentosa	Plant	KNApSAcK
Citrus hassaku	LOTUS Database	35616633
Citrus japonica	LOTUS Database	35616633
Citrus kinokuni	LOTUS Database	35616633
Citrus leiocarpa	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633
Citrus paradisi	FooDB	PHENOL EXPLORER
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus sinensis	LOTUS Database	35616633
Citrus tangerina	Plant	KNApSAcK
Citrus tankan	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clerodendranthus spicatus	-	KNApSAcK
Conoclinium coelestinum	Plant	KNApSAcK
Kickxia spuria	Plant	KNApSAcK
Murraya exotica	LOTUS Database	35616633
Murraya paniculata	Plant	KNApSAcK
Orthosiphon aristatus	Plant	KNApSAcK
Orthosiphon spicatus	Plant	KNApSAcK
Orthosiphon stamineus	Plant	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

3p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavone
Chromone
O-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentamethoxyflavone (CHEBI:9159 )
flavones (C10186 )
Flavones and Flavonols (C10186 )
Flavones and Flavonols (LMPK12111250 )

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	2.98	ALOGPS
logP	2.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.28	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.29 m³·mol⁻¹	ChemAxon
Polarizability	38.96 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0036633

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sinensetin

METLIN ID

Not Available

PubChem Compound

145659

PDB ID

Not Available

ChEBI ID

9159

Good Scents ID

Not Available

References

General References

Kang SI, Shin HS, Ko HC, Kim SJ: Effects of sinensetin on lipid metabolism in mature 3T3-L1 adipocytes. Phytother Res. 2013 Jan;27(1):131-4. doi: 10.1002/ptr.4683. Epub 2012 Mar 22. [PubMed:22438091 ]
Kang SI, Shin HS, Kim SJ: Sinensetin enhances adipogenesis and lipolysis by increasing cyclic adenosine monophosphate levels in 3T3-L1 adipocytes. Biol Pharm Bull. 2015;38(4):552-8. doi: 10.1248/bpb.b14-00700. Epub 2015 Jan 24. [PubMed:25735898 ]

Showing NP-Card for Sinensetin (NP0048557)

MOL for NP0048557 (Sinensetin)

3D MOL for NP0048557 (Sinensetin)

3D SDF for NP0048557 (Sinensetin)

3D-SDF for NP0048557 (Sinensetin)

PDB for NP0048557 (Sinensetin)

3D PDB for NP0048557 (Sinensetin)

SMILES for NP0048557 (Sinensetin)

INCHI for NP0048557 (Sinensetin)

Structure for NP0048557 (Sinensetin)

3D Structure for NP0048557 (Sinensetin)