NP-MRD: Showing NP-Card for Mearnsetin (NP0053017)

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Record Information

Version

2.0

Created at

2022-04-27 23:50:57 UTC

Updated at

2022-04-27 23:50:57 UTC

NP-MRD ID

NP0053017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mearnsetin

Description

Mearnsetin belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, mearnsetin is considered to be a flavonoid lipid molecule. Mearnsetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It can be found in Eucalyptus globulus and in Elaeocarpus lanceofolius. The compound has antioxidative properties. Mearnsetin 3,7-dirhamnoside can be found in the fern Asplenium antiquum. Mearnsetin is found in Acacia mearnsii , Alluaudia ascendens, Flemingia stricta , Landolphia kirkii , Lotus maritimus, Maytenus loevis, Picea neoveitchii, Rhamnus pallasii, Ribes alpinum and Vitex negundo . Mearnsetin is an O-methylated flavonol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    5.9313    1.2451   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2013    0.2071    0.6300 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332    0.0551    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -0.7343   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2264   -1.4075   -1.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -0.8671   -0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777   -0.2504    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -0.3666   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    0.2983    0.7358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582    0.2701    0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.9919    1.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5595    0.9908    1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2585    1.7373    2.5701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2053    0.2485    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397   -0.5128   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2579   -1.2260   -1.2212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483   -0.4762   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.1866   -1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -1.8873   -2.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -1.1037   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -1.8314   -1.9874 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818    0.5502    1.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9321    0.6921    1.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3936    1.4861    2.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458    0.8271   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3242    1.9244    0.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863    1.7724   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862   -1.9832   -2.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -1.4965   -1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6950    1.5971    2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2708    1.7406    2.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2860    0.2236    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979   -1.8039   -1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -2.4003   -2.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667    1.0515    1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3603    1.6245    2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7 22  1  0
 22 23  2  0
 23 24  1  0
  7  8  1  0
  8 20  2  0
 20 21  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
 23  3  1  0
  9  8  1  0
 10 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 22 35  1  0
 24 36  1  0
 21 34  1  0
 16 33  1  0
 14 32  1  0
 13 31  1  0
 11 30  1  0
M  END


  Mrv1533004261512142D          

 24 26  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -1.4289   -1.6500    0.0000 C   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
   -0.7145   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1O)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O8/c1-23-16-9(19)2-6(3-10(16)20)15-14(22)13(21)12-8(18)4-7(17)5-11(12)24-15/h2-5,17-20,22H,1H3

> <INCHI_KEY>
HKEQVXVLTOSXLQ-UHFFFAOYSA-N

> <FORMULA>
C16H12O8

> <MOLECULAR_WEIGHT>
332.264

> <EXACT_MASS>
332.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.473177470823718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.998628198333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.913361380280886

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3808603472703025

> <JCHEM_PKA_STRONGEST_BASIC>
-4.01660807343701

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
83.3254

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mearnsetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+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  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   11                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₈

Average Mass

332.2640 Da

Monoisotopic Mass

332.05322 Da

IUPAC Name

2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

Traditional Name

mearnsetin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1O)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H12O8/c1-23-16-9(19)2-6(3-10(16)20)15-14(22)13(21)12-8(18)4-7(17)5-11(12)24-15/h2-5,17-20,22H,1H3

InChI Key

HKEQVXVLTOSXLQ-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
Acacia mearnsii	Plant	KNApSAcK
Alluaudia ascendens	Plant	KNApSAcK
Flemingia stricta	Plant	KNApSAcK
Landolphia kirkii	Plant	KNApSAcK
Lotus maritimus	LOTUS Database	35616633
Maytenus loevis	Plant	KNApSAcK
Picea neoveitchii	LOTUS Database	35616633
Rhamnus pallasii	Plant	KNApSAcK
Ribes alpinum	LOTUS Database	35616633
Vitex negundo	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
Methoxybenzene
Resorcinol
Anisole
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112506 )

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	1.8	ALOGPS
logP	2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.33 m³·mol⁻¹	ChemAxon
Polarizability	31.47 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mearnsetin

METLIN ID

Not Available

PubChem Compound

10359384

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Mearnsetin (NP0053017)

MOL for NP0053017 (Mearnsetin)

3D MOL for NP0053017 (Mearnsetin)

3D SDF for NP0053017 (Mearnsetin)

3D-SDF for NP0053017 (Mearnsetin)

PDB for NP0053017 (Mearnsetin)

3D PDB for NP0053017 (Mearnsetin)

SMILES for NP0053017 (Mearnsetin)

INCHI for NP0053017 (Mearnsetin)

Structure for NP0053017 (Mearnsetin)

3D Structure for NP0053017 (Mearnsetin)