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Showing NP-Card for 5,7-Dihydroxy-8-methoxyflavone (NP0050632)

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Record Information
Version2.0
Created at2022-04-27 21:59:42 UTC
Updated at2022-04-27 21:59:43 UTC
NP-MRD IDNP0050632
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,7-Dihydroxy-8-methoxyflavone
DescriptionWogonin 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, wogonin is considered to be a flavonoid lipid molecule. Wogonin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5,7-Dihydroxy-8-methoxyflavone is found in Adenostoma sparsifolium, Agrobacterium rhizogenes, Anaphalis sinica, Anodendron affine, Atractylodes lancea, Bupleurum scorzonerifolium , Capparis himalayensis, Eleutherococcus brachypus, Eucommia ulmoides, Holmskioldia sanguinea, Lagochilus leiacanthus, Piper umbellatum, Rhinacanthus nasutus, Saposhnikovia divaricata, Scutellaria alpina, Scutellaria altissima, Scutellaria amabilis, Scutellaria amabilis HARA, Scutellaria amoena, Scutellaria baicalensis, Scutellaria baicalensis GEORGI , Scutellaria barbata , Scutellaria discolor, Scutellaria galericulata, Scutellaria hypericifolia, Scutellaria immaculata, Scutellaria indica, Scutellaria lateriflora, Scutellaria likiangensis, Scutellaria orientalis, Scutellaria planipes, Scutellaria rehderiana, Scutellaria squarrosa, Scutellaria strigillosa, Scutellaria viscidula, Sideritis baicalensis, Stellera dichotoma var.lanceolata, Tetracera asiatica and Tetracera indica . 5,7-Dihydroxy-8-methoxyflavone was first documented in 2000 (PMID: 10724177). A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8 (PMID: 11322923) (PMID: 19438509) (PMID: 22419433) (PMID: 23371323).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)


  Mrv1652310051719402D          

 21 23  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    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
    5.0013   -1.2375    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
    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
    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
    1.4289    0.0000    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    0.8250    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
    2.8579    0.0000    0.0000 C   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
    2.1434   -1.2375    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
  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  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20  1  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
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3D MOL for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)

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3D SDF for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)

  Mrv1652310051719402D          

 21 23  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    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
    5.0013   -1.2375    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
    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
    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
    1.4289    0.0000    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    0.8250    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
    2.8579    0.0000    0.0000 C   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
    2.1434   -1.2375    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
  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  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20  1  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1

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

> <INCHI_KEY>
XLTFNNCXVBYBSX-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.452108022810297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.8525831896666665

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.709774208030542

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.098231547523181

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8328886330315575

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.3962

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wogonin

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)
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PDB for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)
HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   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   13                                                  
CONECT   10    7   14   17                                                  
CONECT   11    8   14   18                                                  
CONECT   12    7   15   19                                                  
CONECT   13    8    9   21                                                  
CONECT   14   10   11   16                                                  
CONECT   15   12   16   20                                                  
CONECT   16   14   15   21                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20    1   15                                                       
CONECT   21   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

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3D PDB for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)
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SMILES for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)
COC1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1
Download
INCHI for NP0050632 (5,7-Dihydroxy-8-methoxyflavone)
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
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View in JSmol
Synonyms
ValueSource
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-8-methoxyflavoneChEBI
Norwogonin 8-methyl etherChEBI
Chemical FormulaC16H12O5
Average Mass284.2670 Da
Monoisotopic Mass284.06847 Da
IUPAC Name5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one
Traditional Namewogonin
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
InChI KeyXLTFNNCXVBYBSX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Adenostoma sparsifoliumPlant
Agrobacterium rhizogenesLOTUS Database
Anaphalis sinicaLOTUS Database
Anodendron affinePlant
Atractylodes lanceaLOTUS Database
Bupleurum scorzonerifoliumPlant
Capparis himalayensisPlant
Eleutherococcus brachypusLOTUS Database
Eucommia ulmoidesLOTUS Database
Holmskioldia sanguineaLOTUS Database
Lagochilus leiacanthusLOTUS Database
Piper umbellatumLOTUS Database
Rhinacanthus nasutusPlant
Saposhnikovia divaricataLOTUS Database
Scutellaria alpinaLOTUS Database
Scutellaria altissimaPlant
Scutellaria amabilisLOTUS Database
Scutellaria amabilis HARAPlant
Scutellaria amoenaPlant
Scutellaria baicalensisLOTUS Database
Scutellaria baicalensis GEORGIPlant
Scutellaria barbataPlant
Scutellaria discolorLOTUS Database
Scutellaria galericulataLOTUS Database
Scutellaria hypericifoliaPlant
Scutellaria immaculataLOTUS Database
Scutellaria indicaPlant
Scutellaria laterifloraLOTUS Database
Scutellaria likiangensisPlant
Scutellaria orientalisLOTUS Database
Scutellaria planipesPlant
Scutellaria rehderianaPlant
Scutellaria squarrosaLOTUS Database
Scutellaria strigillosaLOTUS Database
Scutellaria viscidulaPlant
Sideritis baicalensisPlant
Stellera dichotoma var.lanceolataPlant
Tetracera asiaticaLOTUS Database
Tetracera indicaPlant
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassO-methylated flavonoids  
Direct Parent8-O-methylated flavonoids  
Alternative Parents
Substituents
  • 8-methoxyflavonoid-skeleton
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.43ALOGPS
logP2.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.1ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.4 m³·mol⁻¹ChemAxon
Polarizability28.45 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0153240  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001111  
Chemspider IDNot Available
KEGG Compound IDC10197  
BioCyc IDCPD-12727  
BiGG IDNot Available
Wikipedia LinkWogonin  
METLIN IDNot Available
PubChem Compound5281703  
PDB IDNot Available
ChEBI ID10043  
Good Scents IDNot Available
References
General References
  1. Nagashima S, Hirotani M, Yoshikawa T: Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures. Phytochemistry. 2000 Mar;53(5):533-8. doi: 10.1016/s0031-9422(99)00593-2. [PubMed:10724177  ] 
  2. Chi YS, Cheon BS, Kim HP: Effect of wogonin, a plant flavone from Scutellaria radix, on the suppression of cyclooxygenase-2 and the induction of inducible nitric oxide synthase in lipopolysaccharide-treated RAW 264.7 cells. Biochem Pharmacol. 2001 May 15;61(10):1195-203. doi: 10.1016/s0006-2952(01)00597-4. [PubMed:11322923  ] 
  3. Lee DH, Rhee JG, Lee YJ: Reactive oxygen species up-regulate p53 and Puma; a possible mechanism for apoptosis during combined treatment with TRAIL and wogonin. Br J Pharmacol. 2009 Aug;157(7):1189-202. doi: 10.1111/j.1476-5381.2009.00245.x.  Epub 2009 May 11. [PubMed:19438509  ] 
  4. Lin CM, Chen YH, Ong JR, Ma HP, Shyu KG, Bai KJ: Functional role of wogonin in anti-angiogenesis. Am J Chin Med. 2012;40(2):415-27. doi: 10.1142/S0192415X12500322. [PubMed:22419433  ] 
  5. Yang L, Wang Q, Li D, Zhou Y, Zheng X, Sun H, Yan J, Zhang L, Lin Y, Wang X: Wogonin enhances antitumor activity of tumor necrosis factor-related apoptosis-inducing ligand in vivo through ROS-mediated downregulation of cFLIPL and IAP proteins. Apoptosis. 2013 May;18(5):618-26. doi: 10.1007/s10495-013-0808-8. [PubMed:23371323  ]