NP-MRD: Showing NP-Card for 1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone (NP0237626)

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Record Information

Version

2.0

Created at

2022-09-06 20:49:40 UTC

Updated at

2022-09-06 20:49:40 UTC

NP-MRD ID

NP0237626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone

Description

Orientaloside 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. Orientaloside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Orientaloside has been detected, but not quantified in, herbs and spices. 1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone is found in Rumex hastatus and Rumex patientia. This could make orientaloside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309342D          

 38 41  0  0  0  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  2  0  0  0  0
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 37 25  1  0  0  0  0
 38 23  1  0  0  0  0
 38 24  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05061309342D          

 38 41  0  0  0  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 20  1  0  0  0  0
 23 18  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28 10  2  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 34 22  1  0  0  0  0
 35 12  1  0  0  0  0
 35 25  1  0  0  0  0
 36 13  1  0  0  0  0
 36 24  1  0  0  0  0
 37 14  1  0  0  0  0
 37 25  1  0  0  0  0
 38 23  1  0  0  0  0
 38 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C2=C(C=CC=C2OC2OC(CO)C(O)C(OC3OC(CO)C(O)C(O)C3O)C2O)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O13/c1-9-6-11-4-3-5-12(16(11)19(31)15(9)10(2)28)35-25-22(34)23(18(30)14(8-27)37-25)38-24-21(33)20(32)17(29)13(7-26)36-24/h3-6,13-14,17-18,20-27,29-34H,7-8H2,1-2H3

> <INCHI_KEY>
PFGAJVHSRWCMOQ-UHFFFAOYSA-N

> <FORMULA>
C25H32O13

> <MOLECULAR_WEIGHT>
540.5138

> <EXACT_MASS>
540.18429111

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
53.52983291837474

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethan-1-one

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.9622429016666671

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.935300494735438

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.469145046041922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565339608

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999996

> <JCHEM_REFRACTIVITY>
126.47169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000  15.400   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   12                                                       
CONECT    6    9   11                                                       
CONECT    7   13   26                                                       
CONECT    8   14   27                                                       
CONECT    9    1    6   15                                                  
CONECT   10    2   15   28                                                  
CONECT   11    4    6   16                                                  
CONECT   12    5   16   35                                                  
CONECT   13    7   17   36                                                  
CONECT   14    8   18   37                                                  
CONECT   15    9   10   19                                                  
CONECT   16   11   12   19                                                  
CONECT   17   13   20   29                                                  
CONECT   18   14   23   30                                                  
CONECT   19   15   16   31                                                  
CONECT   20   17   21   32                                                  
CONECT   21   20   24   33                                                  
CONECT   22   23   25   34                                                  
CONECT   23   18   22   38                                                  
CONECT   24   21   36   38                                                  
CONECT   25   22   35   37                                                  
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   12   25                                                       
CONECT   36   13   24                                                       
CONECT   37   14   25                                                       
CONECT   38   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₃

Average Mass

540.5138 Da

Monoisotopic Mass

540.18429 Da

IUPAC Name

1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethan-1-one

Traditional Name

1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C2=C(C=CC=C2OC2OC(CO)C(O)C(OC3OC(CO)C(O)C(O)C3O)C2O)C=C1C

InChI Identifier

InChI=1S/C25H32O13/c1-9-6-11-4-3-5-12(16(11)19(31)15(9)10(2)28)35-25-22(34)23(18(30)14(8-27)37-25)38-24-21(33)20(32)17(29)13(7-26)36-24/h3-6,13-14,17-18,20-27,29-34H,7-8H2,1-2H3

InChI Key

PFGAJVHSRWCMOQ-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
Rumex hastatus	LOTUS Database	35616633
Rumex patientia	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
Disaccharide
1-naphthol
O-glycosyl compound
Naphthalene
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Primary 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
logP	-0.79	ALOGPS
logP	-0.96	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.47 m³·mol⁻¹	ChemAxon
Polarizability	53.53 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

HMDB0037100

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016090

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

131752151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone (NP0237626)

MOL for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

3D MOL for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

3D SDF for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

3D-SDF for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

PDB for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

3D PDB for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

SMILES for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

INCHI for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

Structure for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)

3D Structure for NP0237626 (1-(8-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-3-methylnaphthalen-2-yl)ethanone)