NP-MRD: Showing NP-Card for 7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0153495)

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Record Information

Version

2.0

Created at

2022-09-02 10:10:10 UTC

Updated at

2022-09-02 10:10:11 UTC

NP-MRD ID

NP0153495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

Description

Eriodictyol 5-methyl ether 7-o-xylosyl-(1->4)-arabinoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, eriodictyol 5-methyl ether 7-O-xylosyl-(1->4)-arabinoside is considered to be a flavonoid lipid molecule. 7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one is found in Triadica sebifera. Eriodictyol 5-methyl ether 7-o-xylosyl-(1->4)-arabinoside is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191521522D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191521522D          

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    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   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
  5  6  1  0  0  0  0
  6  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 26 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 33 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OCC(OC3OCC(O)C(O)C3O)C(O)C2O)=CC2=C1C(=O)CC(O2)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O14/c1-35-17-5-11(6-18-20(17)14(29)7-16(39-18)10-2-3-12(27)13(28)4-10)38-25-24(34)22(32)19(9-37-25)40-26-23(33)21(31)15(30)8-36-26/h2-6,15-16,19,21-28,30-34H,7-9H2,1H3

> <INCHI_KEY>
DWVCLXSYYWRHGR-UHFFFAOYSA-N

> <FORMULA>
C26H30O14

> <MOLECULAR_WEIGHT>
566.512

> <EXACT_MASS>
566.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.74739103097821

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-0.7507970703333329

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.87721742080096

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.211590960622418

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806595271325

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
130.38569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

> <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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.669   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19                                                            
CONECT   21   10   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    7   24                                                  
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   26                                                  
CONECT   33   28   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₄

Average Mass

566.5120 Da

Monoisotopic Mass

566.16356 Da

IUPAC Name

7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC2OCC(OC3OCC(O)C(O)C3O)C(O)C2O)=CC2=C1C(=O)CC(O2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H30O14/c1-35-17-5-11(6-18-20(17)14(29)7-16(39-18)10-2-3-12(27)13(28)4-10)38-25-24(34)22(32)19(9-37-25)40-26-23(33)21(31)15(30)8-36-26/h2-6,15-16,19,21-28,30-34H,7-9H2,1H3

InChI Key

DWVCLXSYYWRHGR-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
Triadica sebifera	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
5-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Anisole
Catechol
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Ketone
Secondary alcohol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Aldehyde
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140559 )

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	-0.25	ALOGPS
logP	-0.75	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.39 m³·mol⁻¹	ChemAxon
Polarizability	55.75 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

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

42608065

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0153495)

MOL for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0153495 (7-({3,4-dihydroxy-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)