NP-MRD: Showing NP-Card for Keshonin (NP0086480)

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Record Information

Version

2.0

Created at

2022-04-29 06:46:18 UTC

Updated at

2022-04-29 06:46:18 UTC

NP-MRD ID

NP0086480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Keshonin

Description

[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]beta-D-glucopyranosiduronic acid belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Keshonin is found in Monarda punctata . Based on a literature review very few articles have been published on [3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]beta-D-glucopyranosiduronic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208462D          

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    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
    2.8579    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 26 36  1  0  0  0  0
 24 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 22 40  1  0  0  0  0
 21 41  1  0  0  0  0
 19 42  2  0  0  0  0
 18 43  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 14 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(OC2=C(O)C=CC(=C2)C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3O2)C=C(C)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H30O13/c1-12(2)16-10-18(33)13(3)6-22(16)43-23-7-14(4-5-17(23)32)21-11-20(35)25-19(34)8-15(9-24(25)42-21)41-31-28(38)26(36)27(37)29(44-31)30(39)40/h4-12,26-29,31-34,36-38H,1-3H3,(H,39,40)/t26-,27-,28+,29-,31+/m0/s1

> <INCHI_KEY>
ICDSELIXFBKIOM-SQQOACJHSA-N

> <FORMULA>
C31H30O13

> <MOLECULAR_WEIGHT>
610.568

> <EXACT_MASS>
610.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
60.8178180476677

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-{4-hydroxy-3-[4-hydroxy-5-methyl-2-(propan-2-yl)phenoxy]phenyl}-4-oxo-4H-chromen-7-yl)oxy]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.7140479796666663

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.160345831239255

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.739193296113576

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778068572

> <JCHEM_POLAR_SURFACE_AREA>
212.66999999999996

> <JCHEM_REFRACTIVITY>
152.37939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({5-hydroxy-2-[4-hydroxy-3-(4-hydroxy-2-isopropyl-5-methylphenoxy)phenyl]-4-oxochromen-7-yl}oxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   44                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   43                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   41                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   36                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   26                                                       
CONECT   37   24   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   22                                                       
CONECT   41   21   43                                                       
CONECT   42   19                                                            
CONECT   43   18   41   44                                                  
CONECT   44   43   14                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]b-D-glucopyranosiduronate	Generator
[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]b-D-glucopyranosiduronic acid	Generator
[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]beta-D-glucopyranosiduronate	Generator
[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]β-D-glucopyranosiduronate	Generator
[3'-(2-Isopropyl-4-hydroxy-5-methylphenoxy)-4',5-dihydroxyflavone-7-yl]β-D-glucopyranosiduronic acid	Generator

Chemical Formula

C₃₁H₃₀O₁₃

Average Mass

610.5680 Da

Monoisotopic Mass

610.16864 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-2-{4-hydroxy-3-[4-hydroxy-5-methyl-2-(propan-2-yl)phenoxy]phenyl}-4-oxo-4H-chromen-7-yl)oxy]oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({5-hydroxy-2-[4-hydroxy-3-(4-hydroxy-2-isopropyl-5-methylphenoxy)phenyl]-4-oxochromen-7-yl}oxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(OC2=C(O)C=CC(=C2)C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3O2)C=C(C)C(O)=C1

InChI Identifier

InChI=1S/C31H30O13/c1-12(2)16-10-18(33)13(3)6-22(16)43-23-7-14(4-5-17(23)32)21-11-20(35)25-19(34)8-15(9-24(25)42-21)41-31-28(38)26(36)27(37)29(44-31)30(39)40/h4-12,26-29,31-34,36-38H,1-3H3,(H,39,40)/t26-,27-,28+,29-,31+/m0/s1

InChI Key

ICDSELIXFBKIOM-SQQOACJHSA-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
Monarda punctata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Diphenylether
Chromone
Diaryl ether
Glycosyl compound
O-glycosyl compound
1-benzopyran
P-cymene
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
Cumene
Phenylpropane
Phenoxy compound
O-cresol
Phenol ether
Toluene
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Hydroxy acid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Ether
Carboxylic acid derivative
Carboxylic acid
Polyol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.6	ALOGPS
logP	3.71	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	152.38 m³·mol⁻¹	ChemAxon
Polarizability	60.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056764

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

102053278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Keshonin (NP0086480)

MOL for NP0086480 (Keshonin)

3D MOL for NP0086480 (Keshonin)

3D SDF for NP0086480 (Keshonin)

3D-SDF for NP0086480 (Keshonin)

PDB for NP0086480 (Keshonin)

3D PDB for NP0086480 (Keshonin)

SMILES for NP0086480 (Keshonin)

INCHI for NP0086480 (Keshonin)

Structure for NP0086480 (Keshonin)

3D Structure for NP0086480 (Keshonin)