NP-MRD: Showing NP-Card for 6-Hydroxykaempferol 3,6-dimethylether (NP0048853)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:13 UTC

Updated at

2022-03-17 21:03:13 UTC

NP-MRD ID

NP0048853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxykaempferol 3,6-dimethylether

Description

6-Hydroxykaempferol 3,6-dimethylether is found in Acanthospermum australe, Achillea ligustica, Achillea micrantha, Adenothamnus validus, Aeonium spp., Ageratina espinosara, Ageratina havanensis, Agnorhiza bolanderi, Agnorhiza elata, Alkanna orientalis, Alnus glutinosa , Ambrosia chamissonis, Ambrosia tomentosa, Artemisia ludoviciana, Barbacenia rubro-virens, Betula maximowicziana, Brickellia eupatorioides, Brickellia oliganthes, Brickellia scoparia, Calycadenia multiglandulosa, Calycadenia villosa, Centaurea bracteata Scop., Centaurea jacea, Centaurea phrygia, Centaurea spp., Chiliadenus candicans, Cistus albanicus, Dichrocephala integrifolia, Dittrichia graveolens, Dodonaea viscosa , Eupatorium altissimum, Flourensia cernua, Gardenia spp. , Gonospermum fruticosum, Gonospermum gomerae, Grindelia camporum, Grindelia robusta, Grindelia squarrosa, Gutierrezia wrightii, Heteranthemis viscidehirta, Heterotheca villosa, Oncosiphon grandiflorum, Perityle lemmonii, Perityle vaseyi, Piptadenia stipulacea, Psiadia dentata, Pulicaria paludosa, Salvia cyanescens, Stevia berlandieri, Tanacetum densum, Tanacetum parthenium and Chiliadenus iphionoides.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215272D          

 24 26  0  0  0  0            999 V2000
   -2.8589    1.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301   -0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8589   -0.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424    0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725    0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  2  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 23  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  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
 16 17  1  0  0  0  0
 16 21  2  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 22  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048853

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-16-10(19)7-11-12(13(16)20)14(21)17(23-2)15(24-11)8-3-5-9(18)6-4-8/h3-7,18-20H,1-2H3

> <INCHI_KEY>
DDNPCXHBFYJXBJ-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.52586287082355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.4150209093333332

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.523145052146257

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.955659131733072

> <JCHEM_PKA_STRONGEST_BASIC>
-4.338833859224722

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
86.09570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxychromen-4-one

> <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  O   UNK     0      -5.337   1.922   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.002   1.152   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.670   1.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.335   1.152   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.922   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   3.465   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.670   3.465   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667   1.922   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.332   1.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.332  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -1.158   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.335  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.670  -1.158   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.002  -0.385   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.337  -1.158   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -1.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.002  -3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.334  -2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.334  -1.158   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.002  -0.385   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.669  -3.465   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.999   1.150   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.669   1.150   0.000  0.00  0.00           C+0
CONECT    1    2   24                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    9   23                                                       
CONECT    9    5    8   10                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12    4   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14    2   13   15                                                  
CONECT   15   14                                                            
CONECT   16   10   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   16   20                                                       
CONECT   22   19                                                            
CONECT   23    8                                                            
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
4',5,7-Trihydroxy-3,6-dimethoxyflavone	MeSH

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxy-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxychromen-4-one

CAS Registry Number

22697-65-0

SMILES

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

InChI Identifier

InChI=1S/C17H14O7/c1-22-16-10(19)7-11-12(13(16)20)14(21)17(23-2)15(24-11)8-3-5-9(18)6-4-8/h3-7,18-20H,1-2H3

InChI Key

DDNPCXHBFYJXBJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthospermum australe	LOTUS Database	35616633
Achillea ligustica	LOTUS Database	35616633
Achillea micrantha	Plant	KNApSAcK
Adenothamnus validus	LOTUS Database	35616633
Aeonium spp.	Plant	KNApSAcK
Ageratina espinosara	Plant	KNApSAcK
Ageratina havanensis	Plant	KNApSAcK
Agnorhiza bolanderi	LOTUS Database	35616633
Agnorhiza elata	LOTUS Database	35616633
Alkanna orientalis	Plant	KNApSAcK
Alnus glutinosa	Plant	KNApSAcK
Ambrosia chamissonis	Plant	KNApSAcK
Ambrosia tomentosa	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Barbacenia rubro-virens	Plant	KNApSAcK
Betula maximowicziana	LOTUS Database	35616633
Brickellia eupatorioides	Plant	KNApSAcK
Brickellia oliganthes	LOTUS Database	35616633
Brickellia scoparia	Plant	KNApSAcK
Calycadenia multiglandulosa	Plant	KNApSAcK
Calycadenia villosa	Plant	KNApSAcK
Centaurea bracteata Scop.	Plant	KNApSAcK
Centaurea jacea	LOTUS Database	35616633
Centaurea phrygia	LOTUS Database	35616633
Centaurea spp.	Plant	KNApSAcK
Chiliadenus candicans	LOTUS Database	35616633
Cistus albanicus	Plant	KNApSAcK
Dichrocephala integrifolia	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633
Dodonaea viscosa	Plant	KNApSAcK
Eupatorium altissimum	Plant	KNApSAcK
Flourensia cernua	Plant	KNApSAcK
Gardenia spp.	Plant	KNApSAcK
Gonospermum fruticosum	Plant	KNApSAcK
Gonospermum gomerae	Plant	KNApSAcK
Grindelia camporum	LOTUS Database	35616633
Grindelia robusta	Plant	KNApSAcK
Grindelia squarrosa	Plant	KNApSAcK
Gutierrezia wrightii	Plant	KNApSAcK
Heteranthemis viscidehirta	Plant	KNApSAcK
Heterotheca villosa	Plant	KNApSAcK
Oncosiphon grandiflorum	Plant	KNApSAcK
Perityle lemmonii	Plant	KNApSAcK
Perityle vaseyi	LOTUS Database	35616633
Piptadenia stipulacea	LOTUS Database	35616633
Prunus avium	FooDB	KNAPSACK
Psiadia dentata	Plant	KNApSAcK
Pulicaria paludosa	LOTUS Database	35616633
Salvia cyanescens	Plant	KNApSAcK
Stevia berlandieri	Plant	KNApSAcK
Tanacetum densum	LOTUS Database	35616633
Tanacetum parthenium	Plant	KNApSAcK
Varthemia iphionoides	LOTUS Database	35616633

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
3-methoxyflavonoid-skeleton
Flavone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Anisole
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112867 )

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	2.98	ALOGPS
logP	2.42	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.1 m³·mol⁻¹	ChemAxon
Polarizability	32.53 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016705

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Hydroxykaempferol 3,6-dimethylether (NP0048853)

MOL for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

3D MOL for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

3D SDF for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

3D-SDF for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

PDB for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

3D PDB for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

SMILES for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

INCHI for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

Structure for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)

3D Structure for NP0048853 (6-Hydroxykaempferol 3,6-dimethylether)