NP-MRD: Showing NP-Card for 3',4',5,6,7,8-Hexamethoxyflavone (NP0050623)

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Record Information

Version

2.0

Created at

2022-04-27 21:59:26 UTC

Updated at

2022-04-27 21:59:26 UTC

NP-MRD ID

NP0050623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3',4',5,6,7,8-Hexamethoxyflavone

Description

Nobiletin 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, nobiletin is considered to be a flavonoid lipid molecule. Nobiletin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Nobiletin is a bitter tasting compound. Outside of the human body, Nobiletin is found, on average, in the highest concentration within sweet oranges. Nobiletin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits, lemons, mandarin orange (clementine, tangerine), and sweet bay. This could make nobiletin a potential biomarker for the consumption of these foods. 3',4',5,6,7,8-Hexamethoxyflavone is found in Actinocephalus polyanthus, Ageratina conyzoides, Ageratum conyzoides , Blumea fistulosa, Blumea glomerata, Citrus aurantium , Citrus deliciosa, Citrus depressa, Citrus hassaku , Fortunella japonica , Citrus kinokuni, Citrus mitis, Citrus myrtifolia, Citrus nobilis , Citrus paradisi, Citrus reticulata, Citrus reticulata tangerine , Citrus sinensis, Citrus spp., Citrus tangerina, Citrus tankan, Citrus unshiu, Citrus sinensis , Eupatorium coelestinum, Conoclinium greggii, Eupatorium leucolepis, Eupatorium leucolepsis, Fortunella margarita , Juncus effusus, Laurus nobilis L. , Oxalis pes-caprae, Ozothamnus lycopodioides, Plenodomus tracheiphilus, Tripterygium wilfordii , Viburnum tinus, Viguiera rosei and Xinhui citrus. 3',4',5,6,7,8-Hexamethoxyflavone was first documented in 2003 (PMID: 12787887). A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively (PMID: 25488359) (PMID: 25845666) (PMID: 20670297) (PMID: 15252145).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217282D          

 29 31  0  0  0  0            999 V2000
    1.4023   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    2.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -2.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -3.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -3.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    3.5474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -1.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 29  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  2  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 28  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv0541 02241217282D          

 29 31  0  0  0  0            999 V2000
    1.4023   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    2.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -2.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -3.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -3.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    3.5474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -1.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 29  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  2  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 28  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050623

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

> <INCHI_KEY>
MRIAQLRQZPPODS-UHFFFAOYSA-N

> <FORMULA>
C21H22O8

> <MOLECULAR_WEIGHT>
402.3946

> <EXACT_MASS>
402.13146768

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
41.794221040798135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.021357504666666

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.127322121782655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144891533145286

> <JCHEM_POLAR_SURFACE_AREA>
81.68

> <JCHEM_REFRACTIVITY>
105.75039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nobiletin

> <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       2.618  -0.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.618  -1.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.385  -2.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.385  -4.158   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001  -4.928   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.385  -4.158   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.385  -2.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001  -1.847   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.001  -0.309   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.385   0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.385   2.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.618   2.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.618   4.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.385   5.082   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.001   4.312   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.385   5.082   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.618   4.312   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.771  -4.774   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.080  -6.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.153  -6.468   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.923  -7.546   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.618  -4.928   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.771  -6.468   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.618  -1.847   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.004  -2.463   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.385   6.622   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.155   7.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.001   2.771   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.004  -2.463   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   29                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8   24                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    4   19                                                       
CONECT   19   18                                                            
CONECT   20    5   21                                                       
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22                                                            
CONECT   24    7   25                                                       
CONECT   25   24                                                            
CONECT   26   14   27                                                       
CONECT   27   26                                                            
CONECT   28   11   15                                                       
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
5,6,7,8,3',4'-Hexamethoxyflavone	ChEBI
Hexamethoxyflavone	ChEBI
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ci	HMDB
Flavone, 5,6,7,8,3',4'-hexamethoxy	HMDB

Chemical Formula

C₂₁H₂₂O₈

Average Mass

402.3946 Da

Monoisotopic Mass

402.13147 Da

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one

Traditional Name

nobiletin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

InChI Key

MRIAQLRQZPPODS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinocephalus polyanthus	LOTUS Database	35616633
Ageratina conyzoides	Plant	KNApSAcK
Ageratum conyzoides	Plant	KNApSAcK
Blumea fistulosa	LOTUS Database	35616633
Blumea glomerata	Plant	KNApSAcK
Citrus aurantium	Plant	KNApSAcK
Citrus deliciosa	Plant	KNApSAcK
Citrus depressa	LOTUS Database	35616633
Citrus hassaku	Plant	KNApSAcK
Citrus japonica	Plant	KNApSAcK
Citrus kinokuni	LOTUS Database	35616633
Citrus mitis	Plant	KNApSAcK
Citrus myrtifolia	LOTUS Database	35616633
Citrus nobilis	Plant	KNApSAcK
Citrus paradisi	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Citrus reticulata tangerine	Plant	KNApSAcK
Citrus sinensis	LOTUS Database	35616633
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.)	Plant	KNApSAcK
Conoclinium coelestinum	Plant	KNApSAcK
Conoclinium greggii	Plant	KNApSAcK
Eupatorium leucolepis	LOTUS Database	35616633
Eupatorium leucolepsis	Plant	KNApSAcK
Fortunella margarita	Plant	KNApSAcK
Juncus effusus	LOTUS Database	35616633
Laurus nobilis L.	Plant	KNApSAcK
Oxalis pes-caprae	LOTUS Database	35616633
Ozothamnus lycopodioides	Plant	KNApSAcK
Plenodomus tracheiphilus	LOTUS Database	35616633
Tripterygium wilfordii	Plant	KNApSAcK
Viburnum tinus	LOTUS Database	35616633
Viguiera rosei	Plant	KNApSAcK
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
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyflavone (CHEBI:7602 )
flavones (C10112 )
Flavones and Flavonols (LMPK12111468 )

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	2.62	ALOGPS
logP	2.02	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	41.79 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

HMDB0029540

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

Nobiletin

METLIN ID

Not Available

PubChem Compound

72344

PDB ID

Not Available

ChEBI ID

7602

Good Scents ID

Not Available

References

General References

Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
Kim HJ, Yonezawa T, Teruya T, Woo JT, Cha BY: Nobiletin, a polymethoxy flavonoid, reduced endothelin-1 plus SCF-induced pigmentation in human melanocytes. Photochem Photobiol. 2015 Mar-Apr;91(2):379-86. doi: 10.1111/php.12400. Epub 2015 Jan 12. [PubMed:25488359 ]
Chen J, Chen AY, Huang H, Ye X, Rollyson WD, Perry HE, Brown KC, Rojanasakul Y, Rankin GO, Dasgupta P, Chen YC: The flavonoid nobiletin inhibits tumor growth and angiogenesis of ovarian cancers via the Akt pathway. Int J Oncol. 2015;46(6):2629-38. doi: 10.3892/ijo.2015.2946. Epub 2015 Apr 1. [PubMed:25845666 ]
Kunimasa K, Ikekita M, Sato M, Ohta T, Yamori Y, Ikeda M, Kuranuki S, Oikawa T: Nobiletin, a citrus polymethoxyflavonoid, suppresses multiple angiogenesis-related endothelial cell functions and angiogenesis in vivo. Cancer Sci. 2010 Nov;101(11):2462-9. doi: 10.1111/j.1349-7006.2010.01668.x. [PubMed:20670297 ]
Miyata Y, Sato T, Yano M, Ito A: Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Mol Cancer Ther. 2004 Jul;3(7):839-47. [PubMed:15252145 ]

Showing NP-Card for 3',4',5,6,7,8-Hexamethoxyflavone (NP0050623)

MOL for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

3D MOL for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

3D SDF for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

3D-SDF for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

PDB for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

3D PDB for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

SMILES for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

INCHI for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

Structure for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)

3D Structure for NP0050623 (3',4',5,6,7,8-Hexamethoxyflavone)