NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate (NP0251604)

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Record Information

Version

2.0

Created at

2022-09-07 14:50:55 UTC

Updated at

2022-09-07 14:50:55 UTC

NP-MRD ID

NP0251604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate

Description

4Alpha,8-Dihydroxy-5-[[6-O-(3,5-dihydroxy-4-methoxybenzoyl)-beta-D-glucopyranosyl]oxy]-3,4-dihydronaphthalene-1(2H)-one belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. [(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate is found in Juglans mandshurica. Based on a literature review very few articles have been published on 4alpha,8-Dihydroxy-5-[[6-O-(3,5-dihydroxy-4-methoxybenzoyl)-beta-D-glucopyranosyl]oxy]-3,4-dihydronaphthalene-1(2H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216502D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072216502D          

 37 40  0  0  1  0            999 V2000
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 12 33  1  0  0  0  0
 33 34  1  6  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1O)C(=O)OC[C@H]1O[C@@H](OC2=CC=C(O)C3=C2[C@@H](O)CCC3=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O13/c1-34-22-13(28)6-9(7-14(22)29)23(33)35-8-16-19(30)20(31)21(32)24(37-16)36-15-5-4-11(26)17-10(25)2-3-12(27)18(15)17/h4-7,12,16,19-21,24,26-32H,2-3,8H2,1H3/t12-,16+,19+,20-,21+,24+/m0/s1

> <INCHI_KEY>
LXTPYFMPRPHYEM-DXEMYRHFSA-N

> <FORMULA>
C24H26O13

> <MOLECULAR_WEIGHT>
522.459

> <EXACT_MASS>
522.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.73019081750969

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(8S)-4,8-dihydroxy-5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate

> <JCHEM_LOGP>
0.5556128043333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.520879138320314

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.794916609877857

> <JCHEM_PKA_STRONGEST_BASIC>
-3.262629750121917

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
122.19540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(8S)-4,8-dihydroxy-5-oxo-7,8-dihydro-6H-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.336  11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   3.850   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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27                                                            
CONECT   29   14   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   12   34                                                  
CONECT   34   33                                                            
CONECT   35    7   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
4a,8-Dihydroxy-5-[[6-O-(3,5-dihydroxy-4-methoxybenzoyl)-b-D-glucopyranosyl]oxy]-3,4-dihydronaphthalene-1(2H)-one	Generator
4Α,8-dihydroxy-5-[[6-O-(3,5-dihydroxy-4-methoxybenzoyl)-β-D-glucopyranosyl]oxy]-3,4-dihydronaphthalene-1(2H)-one	Generator

Chemical Formula

C₂₄H₂₆O₁₃

Average Mass

522.4590 Da

Monoisotopic Mass

522.13734 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1O)C(=O)OC[C@H]1O[C@@H](OC2=CC=C(O)C3=C2[C@@H](O)CCC3=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C24H26O13/c1-34-22-13(28)6-9(7-14(22)29)23(33)35-8-16-19(30)20(31)21(32)24(37-16)36-15-5-4-11(26)17-10(25)2-3-12(27)18(15)17/h4-7,12,16,19-21,24,26-32H,2-3,8H2,1H3/t12-,16+,19+,20-,21+,24+/m0/s1

InChI Key

LXTPYFMPRPHYEM-DXEMYRHFSA-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
Juglans mandshurica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Gallic acid or derivatives
M-hydroxybenzoic acid ester
O-glycosyl compound
P-methoxybenzoic acid or derivatives
Methoxyphenol
Tetralin
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Resorcinol
Benzoyl
Anisole
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid ester
Secondary alcohol
Polyol
Ether
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Aldehyde
Alcohol
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

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

101012984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate (NP0251604)

MOL for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

3D MOL for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

3D SDF for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

3D-SDF for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

PDB for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

3D PDB for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

SMILES for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

INCHI for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

Structure for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)

3D Structure for NP0251604 ([(2r,3s,4s,5r,6s)-6-{[(8s)-4,8-dihydroxy-5-oxo-7,8-dihydro-6h-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,5-dihydroxy-4-methoxybenzoate)