NP-MRD: Showing NP-Card for (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate (NP0296332)

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Record Information

Version

2.0

Created at

2022-09-10 05:50:55 UTC

Updated at

2022-09-10 05:50:55 UTC

NP-MRD ID

NP0296332

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate

Description

(6-{[2-(3,4-Dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate belongs to the class of organic compounds known as 7-o-methylated flavonoids. (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate is found in Buphthalmum salicifolium. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518212D          

 40 43  0  0  0  0            999 V2000
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    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
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    9.2881   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191518212D          

 40 43  0  0  0  0            999 V2000
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  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 15 16  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
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296332

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OCC1OC(OC2=CC3=C(C(O)=C2O)C(=O)C(O)=C(O3)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c1-9(2)5-16(29)37-8-15-19(31)22(34)24(36)26(40-15)39-14-7-13-17(20(32)18(14)30)21(33)23(35)25(38-13)10-3-4-11(27)12(28)6-10/h3-4,6-7,9,15,19,22,24,26-28,30-32,34-36H,5,8H2,1-2H3

> <INCHI_KEY>
JJDVTBGHKGLZLP-UHFFFAOYSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.72522713203285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.4579150676666663

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.444165451799371

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.287470297559459

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102930592308

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999998

> <JCHEM_REFRACTIVITY>
133.9155

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      16.004  -6.160   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.338  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.339  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.006  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.006  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.340  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.340  -8.470   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      26.674  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      26.674 -10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      25.340 -13.090   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      24.006 -10.780   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.673 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      24.006  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.673  -8.470   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.339  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      22.673  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.339  -6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      28.007 -11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.341 -10.780   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.675 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.675 -13.090   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      32.008 -13.860   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      29.341 -13.860   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      29.341 -15.400   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      28.007 -13.090   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.673  -2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      24.006  -1.540   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      21.339   0.000   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25                                                            
CONECT   27   17   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   11   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    9   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate

Traditional Name

(6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OCC1OC(OC2=CC3=C(C(O)=C2O)C(=O)C(O)=C(O3)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H28O14/c1-9(2)5-16(29)37-8-15-19(31)22(34)24(36)26(40-15)39-14-7-13-17(20(32)18(14)30)21(33)23(35)25(38-13)10-3-4-11(27)12(28)6-10/h3-4,6-7,9,15,19,22,24,26-28,30-32,34-36H,5,8H2,1-2H3

InChI Key

JJDVTBGHKGLZLP-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Buphthalmum salicifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
6-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Chromone
M-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	2.21	ALOGPS
logP	1.46	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.92 m³·mol⁻¹	ChemAxon
Polarizability	54.73 Å³	ChemAxon
Number of Rings	4	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate (NP0296332)

MOL for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

3D MOL for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

3D SDF for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

3D-SDF for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

PDB for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

3D PDB for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

SMILES for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

INCHI for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

Structure for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)

3D Structure for NP0296332 ((6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-methylbutanoate)