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Showing NP-Card for 7-Hydroxy-3',4',5,6-tetramethoxyflavone (NP0049248)

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Record Information
Version2.0
Created at2022-03-17 21:09:26 UTC
Updated at2022-03-17 21:09:27 UTC
NP-MRD IDNP0049248
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-Hydroxy-3',4',5,6-tetramethoxyflavone
Description7-Hydroxy-3',4',5,6-tetramethoxyflavone, also known as 6-hydroxyluteolin 5,6,3',4'-tetramethyl 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, 7-hydroxy-3',4',5,6-tetramethoxyflavone is considered to be a flavonoid lipid molecule. 7-Hydroxy-3',4',5,6-tetramethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 7-Hydroxy-3',4',5,6-tetramethoxyflavone has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). 7-Hydroxy-3',4',5,6-tetramethoxyflavone is found in Citrus and Citrus japonica. This could make 7-hydroxy-3',4',5,6-tetramethoxyflavone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)


  Mrv0541 02241214412D          

 26 28  0  0  0  0            999 V2000
   -0.3568    2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3568    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
    1.0718   -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
    1.7867   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5003    2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
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  4  6  1  0  0  0  0
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  9 12  1  0  0  0  0
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 25 26  1  0  0  0  0
M  END
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3D MOL for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)

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3D SDF for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)

  Mrv0541 02241214412D          

 26 28  0  0  0  0            999 V2000
   -0.3568    2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    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
    1.0718   -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
    1.7867   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5 17  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 23  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049248

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-22-13-6-5-10(7-15(13)23-2)14-8-11(20)17-16(26-14)9-12(21)18(24-3)19(17)25-4/h5-9,21H,1-4H3

> <INCHI_KEY>
QZNYGJAJWILZLF-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.96624412450102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.0331347143333334

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.70902191841812

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.091800780978549

> <JCHEM_PKA_STRONGEST_BASIC>
-4.289160846923533

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
94.8049

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)
Download
PDB for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)
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  O   UNK     0      -0.666   4.235   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.666   2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.666   1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.666   0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.666  -0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.335  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.667  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.335   0.385   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.002  -2.695   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.334  -1.925   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.002  -0.385   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.667   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.335  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.001   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.335   2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.667   1.925   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.002   2.695   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.334   1.925   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.335  -4.235   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.667  -5.005   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.335   4.235   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.667   5.005   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4   17                                                       
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10                                                       
CONECT   12    9   13                                                       
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17    5   16   18                                                  
CONECT   18    2   17   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   15   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    8   24                                                       
CONECT   24   23                                                            
CONECT   25   19   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Download
3D PDB for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)
Download
SMILES for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2OC
Download
INCHI for NP0049248 (7-Hydroxy-3',4',5,6-tetramethoxyflavone)
InChI=1S/C19H18O7/c1-22-13-6-5-10(7-15(13)23-2)14-8-11(20)17-16(26-14)9-12(21)18(24-3)19(17)25-4/h5-9,21H,1-4H3
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View in JSmol
Synonyms
ValueSource
6-Hydroxyluteolin 5,6,3',4'-tetramethyl etherHMDB
Chemical FormulaC19H18O7
Average Mass358.3420 Da
Monoisotopic Mass358.10525 Da
IUPAC Name2-(3,4-dimethoxyphenyl)-7-hydroxy-5,6-dimethoxy-4H-chromen-4-one
Traditional Name2-(3,4-dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one
CAS Registry Number40983-99-1
SMILES
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2OC
InChI Identifier
InChI=1S/C19H18O7/c1-22-13-6-5-10(7-15(13)23-2)14-8-11(20)17-16(26-14)9-12(21)18(24-3)19(17)25-4/h5-9,21H,1-4H3
InChI KeyQZNYGJAJWILZLF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus ×limon (L.) Burm. f. (pro sp.)-
Citrus japonicaLOTUS Database
Citrus reticulataFooDB
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassO-methylated flavonoids  
Direct Parent6-O-methylated flavonoids  
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
    • 

  • 4p-methoxyflavonoid-skeleton
    • 

  • 5-methoxyflavonoid-skeleton
    • 

  • 6-methoxyflavonoid-skeleton
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • O-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Pyran
    • 

  • Vinylogous ester
    • 

  • Heteroaromatic compound
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP2.96ALOGPS
logP2.03ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.8 m³·mol⁻¹ChemAxon
Polarizability36.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038845  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018280  
KNApSAcK IDC00003897  
Chemspider ID4590620  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5491643  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available