NP-MRD: Showing NP-Card for 3,5-Dimethylquercetin (NP0048735)

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Record Information

Version

2.0

Created at

2022-03-17 21:01:21 UTC

Updated at

2022-03-17 21:01:22 UTC

NP-MRD ID

NP0048735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dimethylquercetin

Description

Caryatin belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Thus, caryatin is considered to be a flavonoid lipid molecule. Caryatin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Caryatin has been detected, but not quantified in, nuts and pecan nuts. 3,5-Dimethylquercetin is found in Achyrocline tomentosa, Aeonium arboreum, Alnus alnobetula, Artemisia abrotanum, Artemisia monosperma, Brickellia glutinosa, Calceolaria tripartita, Carya, Carya pecan, Cistus laurifolius, Dioscorea bulbifera , Ericameria laricifolia, Eucryphia cordifolia, Eucryphia glutinosa, Holocarpha heermannii, Mirabilis viscosa, Pulicaria incisa, Rhododendron jasminiflorum, Rhododendron spp., Salpiglossis sinuata and Scapholeberis mucronata. This could make caryatin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309442D          

 24 26  0  0  0  0            999 V2000
   -0.7145   -2.8875    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
    3.5724   -0.4125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289   -1.6500    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 15  2  0  0  0  0
 22  1  1  0  0  0  0
 22 12  1  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
 24 13  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C(OC)=C(OC2=CC(O)=C1)C1=CC(O)=C(O)C=C1

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

> <INCHI_KEY>
AOFQCVDYMNHCKD-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.564342741995375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
1.765020909333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.561981417748694

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.376003408675079

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587330520075048

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
86.09570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caryatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8    3    5   16                                                  
CONECT    9    6    7   18                                                  
CONECT   10    4   11   19                                                  
CONECT   11    5   10   20                                                  
CONECT   12    6   14   22                                                  
CONECT   13    7   14   24                                                  
CONECT   14   12   13   15                                                  
CONECT   15   14   17   21                                                  
CONECT   16    8   17   24                                                  
CONECT   17   15   16   23                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   15                                                            
CONECT   22    1   12                                                       
CONECT   23    2   17                                                       
CONECT   24   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
35-O-Dimethylquercetin	HMDB
2-(3,4-Dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-4H-1-benzopyran-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-4H-1-benzopyran-4-one, 9ci	HMDB
3,5-Di-O-methylquercetin	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-4H-chromen-4-one

Traditional Name

caryatin

CAS Registry Number

1486-66-4

SMILES

COC1=C2C(=O)C(OC)=C(OC2=CC(O)=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

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

InChI Key

AOFQCVDYMNHCKD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achyrocline tomentosa	LOTUS Database	35616633
Aeonium arboreum	LOTUS Database	35616633
Alnus viridis	LOTUS Database	35616633
Artemisia abrotanum	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Brickellia glutinosa	LOTUS Database	35616633
Calceolaria tripartita	LOTUS Database	35616633
Carya	-	KNApSAcK
Carya illinoinensis	FooDB	KNAPSACK
Carya pecan	Plant	KNApSAcK
Cistus laurifolius	LOTUS Database	35616633
Dioscorea bulbifera	Plant	KNApSAcK
Ericameria laricifolia	LOTUS Database	35616633
Eucryphia cordifolia	Plant	KNApSAcK
Eucryphia glutinosa	Plant	KNApSAcK
Holocarpha heermannii	LOTUS Database	35616633
Mirabilis viscosa	LOTUS Database	35616633
Pulicaria incisa	LOTUS Database	35616633
Rhododendron jasminiflorum	LOTUS Database	35616633
Rhododendron spp.	Plant	KNApSAcK
Salpiglossis sinuata	LOTUS Database	35616633
Scapholeberis mucronata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112730 )

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	3.02	ALOGPS
logP	1.77	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4.6	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	32.56 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

HMDB0037351

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016373

KNApSAcK ID

C00004637

Chemspider ID

4590169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5489501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,5-Dimethylquercetin (NP0048735)

MOL for NP0048735 (3,5-Dimethylquercetin)

3D MOL for NP0048735 (3,5-Dimethylquercetin)

3D SDF for NP0048735 (3,5-Dimethylquercetin)

3D-SDF for NP0048735 (3,5-Dimethylquercetin)

PDB for NP0048735 (3,5-Dimethylquercetin)

3D PDB for NP0048735 (3,5-Dimethylquercetin)

SMILES for NP0048735 (3,5-Dimethylquercetin)

INCHI for NP0048735 (3,5-Dimethylquercetin)

Structure for NP0048735 (3,5-Dimethylquercetin)

3D Structure for NP0048735 (3,5-Dimethylquercetin)