NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate (NP0324187)

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Record Information

Version

2.0

Created at

2022-09-12 04:06:26 UTC

Updated at

2022-09-12 04:06:26 UTC

NP-MRD ID

NP0324187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate

Description

J3.582.459F belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. [(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate is found in Rumex acetosa. Based on a literature review very few articles have been published on J3.582.459F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206062D          

 35 37  0  0  1  0            999 V2000
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122206062D          

 35 37  0  0  1  0            999 V2000
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0324187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C(=O)OC[C@H]1O[C@@H](OC2=C(O)C=C(O)C=C2OC)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O13/c1-30-12-4-9(5-13(31-2)16(12)25)21(29)33-8-15-17(26)18(27)19(28)22(34-15)35-20-11(24)6-10(23)7-14(20)32-3/h4-7,15,17-19,22-28H,8H2,1-3H3/t15-,17-,18+,19-,22+/m1/s1

> <INCHI_KEY>
SWFZYDZNIKLUJF-LNBCOLIQSA-N

> <FORMULA>
C22H26O13

> <MOLECULAR_WEIGHT>
498.437

> <EXACT_MASS>
498.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.41086866476164

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate

> <JCHEM_LOGP>
0.5132024876666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.601686172423372

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.404525300618202

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64911052197378

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
115.3376

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -12.003  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   12   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   10   29                                                  
CONECT   29   28                                                            
CONECT   30    5   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₃

Average Mass

498.4370 Da

Monoisotopic Mass

498.13734 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C(=O)OC[C@H]1O[C@@H](OC2=C(O)C=C(O)C=C2OC)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C22H26O13/c1-30-12-4-9(5-13(31-2)16(12)25)21(29)33-8-15-17(26)18(27)19(28)22(34-15)35-20-11(24)6-10(23)7-14(20)32-3/h4-7,15,17-19,22-28H,8H2,1-3H3/t15-,17-,18+,19-,22+/m1/s1

InChI Key

SWFZYDZNIKLUJF-LNBCOLIQSA-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
Rumex acetosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Gallic acid or derivatives
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Glycosyl compound
Methoxyphenol
Benzoate ester
M-dimethoxybenzene
Dimethoxybenzene
4-alkoxyphenol
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Resorcinol
Anisole
Benzoyl
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Polyol
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.51	ChemAxon
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	115.34 m³·mol⁻¹	ChemAxon
Polarizability	47.41 Å³	ChemAxon
Number of Rings	3	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

132530686

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-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate (NP0324187)

MOL for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

3D MOL for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

3D SDF for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

3D-SDF for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

PDB for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

3D PDB for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

SMILES for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

INCHI for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

Structure for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)

3D Structure for NP0324187 ([(2r,3s,4s,5r,6s)-6-(2,4-dihydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate)