NP-MRD: Showing NP-Card for Oroxylin A (NP0052242)

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Record Information

Version

2.0

Created at

2022-04-27 23:22:21 UTC

Updated at

2022-04-27 23:22:21 UTC

NP-MRD ID

NP0052242

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oroxylin A

Description

5,7-Dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, also known as 5,7-dihydroxy-6-methoxyflavone or baicalein 6-methyl ether, belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one is considered to be a flavonoid lipid molecule. Oroxylin A is found in Adenostoma sparsifolium, Agrobacterium rhizogenes, Bupleurum scorzonerifolium , Capparis himalayensis, Carthamus glauca, Centaurea pseudoscabiosa, Eucommia ulmoides, Flourensia laurifolia, Gomphrena boliviana, Gomphrena martiana, Lagochilus leiacanthus, Muntingia calabura, Oroxylum indicum , Pajanelia multijuga, Phonus arborescens, Rhinacanthus nasutus, Scutellaria alpina, Scutellaria altissima, Scutellaria amoena, Scutellaria baicalensis, Scutellaria baicalensis GEORGI , Scutellaria galericulata, Scutellaria hypericifolia, Scutellaria lateriflora, Scutellaria likiangensis, Scutellaria racemosa, Scutellaria rehderiana, Scutellaria seleriana, Scutellaria squarrosa, Scutellaria strigillosa and Scutellaria viscidula. Oroxylin A was first documented in 2003 (PMID: 12818372). 5,7-Dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 22366656) (PMID: 22560876) (PMID: 23238475) (PMID: 23371806).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.6041   -0.3405    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7106    0.2055   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    0.3406   -0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    1.4720    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569    2.4885    0.7016 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    1.5852    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    0.5622    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224    0.6447    0.2867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729   -0.2930   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0070   -0.1184    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560    1.0731    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7717    1.3390    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7187    0.3948    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3144   -0.7826    0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665   -1.0409   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692   -1.4403   -0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -1.5849   -0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145   -2.6057   -1.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -0.5673   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108   -0.6604   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9926   -1.8212   -1.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4153   -0.9147    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356   -1.0701    1.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    0.4356    1.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    3.3546    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    2.4706    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061    1.8137    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1305    2.2562    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7882    0.5606    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0212   -1.5481   -0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671   -1.9785   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -2.2687   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854   -1.9615   -1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20 21  1  0
 20 19  1  0
 19  7  2  0
  7  8  1  0
  8  9  1  0
  9 16  2  0
 16 17  1  0
 17 18  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
 17 19  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 33  1  0
 16 32  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
  6 26  1  0
  5 25  1  0
M  END


  Mrv1652308211903552D          

 21 23  0  0  0  0            999 V2000
    3.5724    2.0625    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
   -2.1434   -0.4125    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
   -1.4289    0.0000    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
   -0.7145    2.0625    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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
   -0.7145    1.2375    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(OC(=CC2=O)C2=CC=CC=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3

> <INCHI_KEY>
LKOJGSWUMISDOF-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.680965300690538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.8525831896666665

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.68257344469388

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.101283686098633

> <JCHEM_PKA_STRONGEST_BASIC>
-4.811425125060423

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.3962

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oroxylin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0       6.668   3.850   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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   12                                                       
CONECT    8   11   13                                                       
CONECT    9    5    6   12                                                  
CONECT   10    7   14   17                                                  
CONECT   11    8   16   18                                                  
CONECT   12    7    9   21                                                  
CONECT   13    8   14   21                                                  
CONECT   14   10   13   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   11   15   20                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   15                                                            
CONECT   20    1   16                                                       
CONECT   21   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-6-methoxyflavone	ChEBI
Baicalein 6-methyl ether	ChEBI
Oroxylin	MeSH
5,7-Dihydroxy-6-methoxy-2-phenylchromen-4-one	MeSH

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

oroxylin A

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(OC(=CC2=O)C2=CC=CC=C2)C=C1O

InChI Identifier

InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3

InChI Key

LKOJGSWUMISDOF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenostoma sparsifolium	Plant	KNApSAcK
Agrobacterium rhizogenes	LOTUS Database	35616633
Bupleurum scorzonerifolium	Plant	KNApSAcK
Capparis himalayensis	Plant	KNApSAcK
Carthamus glauca	Plant	KNApSAcK
Centaurea pseudoscabiosa	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Flourensia laurifolia	Plant	KNApSAcK
Gomphrena boliviana	Plant	KNApSAcK
Gomphrena martiana	Plant	KNApSAcK
Lagochilus leiacanthus	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Oroxylum indicum	Plant	KNApSAcK
Pajanelia multijuga	Plant	KNApSAcK
Phonus arborescens	LOTUS Database	35616633
Rhinacanthus nasutus	Plant	KNApSAcK
Scutellaria alpina	LOTUS Database	35616633
Scutellaria altissima	LOTUS Database	35616633
Scutellaria amoena	Plant	KNApSAcK
Scutellaria baicalensis	LOTUS Database	35616633
Scutellaria baicalensis GEORGI	Plant	KNApSAcK
Scutellaria galericulata	LOTUS Database	35616633
Scutellaria hypericifolia	Plant	KNApSAcK
Scutellaria lateriflora	LOTUS Database	35616633
Scutellaria likiangensis	Plant	KNApSAcK
Scutellaria racemosa	LOTUS Database	35616633
Scutellaria rehderiana	Plant	KNApSAcK
Scutellaria seleriana	Plant	KNApSAcK
Scutellaria squarrosa	LOTUS Database	35616633
Scutellaria strigillosa	LOTUS Database	35616633
Scutellaria viscidula	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:61668 )
monomethoxyflavone (CHEBI:61668 )
Flavones and Flavonols (LMPK12111096 )
a flavone (CPD-12734 )

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	3.47	ALOGPS
logP	2.85	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.1	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.4 m³·mol⁻¹	ChemAxon
Polarizability	28.68 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

HMDB0128584

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087437

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-12734

BiGG ID

Not Available

Wikipedia Link

Oroxylin_A

METLIN ID

Not Available

PubChem Compound

5320315

PDB ID

Not Available

ChEBI ID

61668

Good Scents ID

Not Available

References

General References

Huen MS, Leung JW, Ng W, Lui WS, Chan MN, Wong JT, Xue H: 5,7-Dihydroxy-6-methoxyflavone, a benzodiazepine site ligand isolated from Scutellaria baicalensis Georgi, with selective antagonistic properties. Biochem Pharmacol. 2003 Jul 1;66(1):125-32. doi: 10.1016/s0006-2952(03)00233-8. [PubMed:12818372 ]
Pham TA, Che H, Phan PT, Lee JW, Kim SS, Park H: Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2534-5. doi: 10.1016/j.bmcl.2012.01.135. Epub 2012 Feb 8. [PubMed:22366656 ]
Zou M, Lu N, Hu C, Liu W, Sun Y, Wang X, You Q, Gu C, Xi T, Guo Q: Beclin 1-mediated autophagy in hepatocellular carcinoma cells: implication in anticancer efficiency of oroxylin A via inhibition of mTOR signaling. Cell Signal. 2012 Aug;24(8):1722-32. doi: 10.1016/j.cellsig.2012.04.009. Epub 2012 Apr 25. [PubMed:22560876 ]
Song X, Chen Y, Sun Y, Lin B, Qin Y, Hui H, Li Z, You Q, Lu N, Guo Q: Oroxylin A, a classical natural product, shows a novel inhibitory effect on angiogenesis induced by lipopolysaccharide. Pharmacol Rep. 2012;64(5):1189-99. doi: 10.1016/s1734-1140(12)70915-5. [PubMed:23238475 ]
Yoon SY, dela Pena I, Kim SM, Woo TS, Shin CY, Son KH, Park H, Lee YS, Ryu JH, Jin M, Kim KM, Cheong JH: Oroxylin A improves attention deficit hyperactivity disorder-like behaviors in the spontaneously hypertensive rat and inhibits reuptake of dopamine in vitro. Arch Pharm Res. 2013 Jan;36(1):134-40. doi: 10.1007/s12272-013-0009-6. [PubMed:23371806 ]

Showing NP-Card for Oroxylin A (NP0052242)

MOL for NP0052242 (Oroxylin A)

3D MOL for NP0052242 (Oroxylin A)

3D SDF for NP0052242 (Oroxylin A)

3D-SDF for NP0052242 (Oroxylin A)

PDB for NP0052242 (Oroxylin A)

3D PDB for NP0052242 (Oroxylin A)

SMILES for NP0052242 (Oroxylin A)

INCHI for NP0052242 (Oroxylin A)

Structure for NP0052242 (Oroxylin A)

3D Structure for NP0052242 (Oroxylin A)