NP-MRD: Showing NP-Card for Isosinensetin (NP0048854)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:14 UTC

Updated at

2022-03-17 21:03:14 UTC

NP-MRD ID

NP0048854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isosinensetin

Description

Isosinensetin 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, isosinensetin is considered to be a flavonoid lipid molecule. Isosinensetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isosinensetin has been detected, but not quantified in, several different foods, such as citrus, fruits, mandarin orange (clementine, tangerine), and sweet oranges. Isosinensetin is found in Citrus aurantifolia , Citrus aurantium , Citrus grandis var.tomentosa , Citrus hassaku , Fortunella japonica , Citrus kinokuni, Citrus paradisi , Citrus spp., Citrus tangerina, Citrus tankan, Citrus unshiu, Ficus altissima , Fortunella margarita , Mandarina satsuma, Muntingia calabura, Nelumbo nucifera , Neoraputia alba, Sideritis incana and Xinhui citrus. This could make isosinensetin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209282D          

 27 29  0  0  0  0            999 V2000
    2.5005   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9305    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  2  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 22  1  0  0  0  0
 16 21  1  0  0  0  0
 18 26  1  0  0  0  0
 19 23  1  0  0  0  0
 20 27  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END


  Mrv0541 02241209282D          

 27 29  0  0  0  0            999 V2000
    2.5005   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9305    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  2  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 22  1  0  0  0  0
 16 21  1  0  0  0  0
 18 26  1  0  0  0  0
 19 23  1  0  0  0  0
 20 27  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2OC

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

> <INCHI_KEY>
UYCWETIUOAGWIL-UHFFFAOYSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.3686

> <EXACT_MASS>
372.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.80617706390403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,7,8-trimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.99

> <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>
15.25448568528391

> <JCHEM_PKA_STRONGEST_BASIC>
-4.189082567543473

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
99.28719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isosinensetin

> <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  C   UNK     0       4.668  -1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.668  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.335   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.335  -2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.666   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.666   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.666   2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.666  -0.385   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.333   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.668   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.668   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.333  -0.385   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.666   4.235   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.002  -2.695   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.335  -4.235   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.333   4.235   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.333  -1.925   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.002  -0.385   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.001  -5.005   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.668  -2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.337   0.385   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.337  -1.925   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.668   5.005   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   19                                                  
CONECT    7    4    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12   16                                                  
CONECT   12    7   11                                                       
CONECT   13   10   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   11   15   21                                                  
CONECT   17    9                                                            
CONECT   18    1   26                                                       
CONECT   19    6   23                                                       
CONECT   20   13   27                                                       
CONECT   21   16   24                                                       
CONECT   22   15   25                                                       
CONECT   23   19                                                            
CONECT   24   21                                                            
CONECT   25   22                                                            
CONECT   26   18                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
5783'4'-Pentamethoxyflavone	HMDB
2-(3,4-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-1-benzopyran-4-one	HMDB
3',4',5,7,8-Pentamethoxyflavone	HMDB
5,7,8,3',4'-Pentamethoxyflavone	HMDB
6-Demethoxynobiletin	HMDB

Chemical Formula

C₂₀H₂₀O₇

Average Mass

372.3686 Da

Monoisotopic Mass

372.12090 Da

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,7,8-trimethoxy-4H-chromen-4-one

Traditional Name

isosinensetin

CAS Registry Number

17290-70-9

SMILES

COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2OC

InChI Identifier

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

InChI Key

UYCWETIUOAGWIL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantiifolia	Plant	KNApSAcK
Citrus aurantium	Plant	KNApSAcK
Citrus grandis var.tomentosa	Plant	KNApSAcK
Citrus hassaku	Plant	KNApSAcK
Citrus japonica	Plant	KNApSAcK
Citrus kinokuni	LOTUS Database	35616633
Citrus paradisi	Plant	KNApSAcK
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus spp.	Plant	KNApSAcK
Citrus tangerina	LOTUS Database	35616633
Citrus tankan	Plant	KNApSAcK
Citrus unshiu	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ficus altissima	Plant	KNApSAcK
Fortunella margarita	Plant	KNApSAcK
Mandarina satsuma	Animalia	KNApSAcK
Muntingia calabura	LOTUS Database	35616633
Nelumbo nucifera	Plant	KNApSAcK
Neoraputia alba	LOTUS Database	35616633
Sideritis incana	LOTUS Database	35616633
Xinhui citrus	-	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

3p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-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

Flavones and Flavonols (LMPK12111403 )

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	2.99	ALOGPS
logP	2.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.25	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	38.81 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

HMDB0037599

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016709

KNApSAcK ID

C00003912

Chemspider ID

548876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

632135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isosinensetin (NP0048854)

MOL for NP0048854 (Isosinensetin)

3D MOL for NP0048854 (Isosinensetin)

3D SDF for NP0048854 (Isosinensetin)

3D-SDF for NP0048854 (Isosinensetin)

PDB for NP0048854 (Isosinensetin)

3D PDB for NP0048854 (Isosinensetin)

SMILES for NP0048854 (Isosinensetin)

INCHI for NP0048854 (Isosinensetin)

Structure for NP0048854 (Isosinensetin)

3D Structure for NP0048854 (Isosinensetin)