NP-MRD: Showing NP-Card for {3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0206814)

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Record Information

Version

1.0

Created at

2022-09-05 03:12:07 UTC

Updated at

2022-09-05 03:12:07 UTC

NP-MRD ID

NP0206814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Description

Eugenol O-[3,4,5-Trihydroxybenzoyl-(->6)-b-D-glucopyranoside] 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. Eugenol O-[3,4,5-Trihydroxybenzoyl-(->6)-b-D-glucopyranoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Eugenol O-[3,4,5-Trihydroxybenzoyl-(->6)-b-D-glucopyranoside] has been detected, but not quantified in, herbs and spices. {3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate is found in Pimenta dioica and Syzygium aromaticum. This could make eugenol O-[3,4,5-trihydroxybenzoyl-(->6)-b-D-glucopyranoside] a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312042D          

 34 36  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    3.7125    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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    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
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 34 23  1  0  0  0  0
M  END

     RDKit          3D

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    9.7472   -1.0335   -0.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061312042D          

 34 36  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0206814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C=CC(CC=C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c1-3-4-11-5-6-15(16(7-11)31-2)33-23-21(29)20(28)19(27)17(34-23)10-32-22(30)12-8-13(24)18(26)14(25)9-12/h3,5-9,17,19-21,23-29H,1,4,10H2,2H3

> <INCHI_KEY>
MXIGGCCKAQLWPD-UHFFFAOYSA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.4459

> <EXACT_MASS>
478.147511674

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
47.120910330284346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.9271157519999997

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.235981009684261

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.107865675476035

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110501585147

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
116.69849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  17.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  15.400   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  O   UNK     0      -2.667  15.400   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000  20.020   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667  18.480   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   31                                                            
CONECT    3    1    4                                                       
CONECT    4    3   11                                                       
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7   11   16                                                       
CONECT    8   12   13                                                       
CONECT    9   12   14                                                       
CONECT   10   17   32                                                       
CONECT   11    4    5    7                                                  
CONECT   12    8    9   22                                                  
CONECT   13    8   18   24                                                  
CONECT   14    9   18   25                                                  
CONECT   15    6   16   33                                                  
CONECT   16    7   15   31                                                  
CONECT   17   10   19   34                                                  
CONECT   18   13   14   26                                                  
CONECT   19   17   20   27                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   23   29                                                  
CONECT   22   12   30   32                                                  
CONECT   23   21   33   34                                                  
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31    2   16                                                       
CONECT   32   10   22                                                       
CONECT   33   15   23                                                       
CONECT   34   17   23                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₃H₂₆O₁₁

Average Mass

478.4459 Da

Monoisotopic Mass

478.14751 Da

IUPAC Name

{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Traditional Name

{3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C=CC(CC=C)=C1

InChI Identifier

InChI=1S/C23H26O11/c1-3-4-11-5-6-15(16(7-11)31-2)33-23-21(29)20(28)19(27)17(34-23)10-32-22(30)12-8-13(24)18(26)14(25)9-12/h3,5-9,17,19-21,23-29H,1,4,10H2,2H3

InChI Key

MXIGGCCKAQLWPD-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
Pimenta dioica	LOTUS Database	35616633
Syzygium aromaticum	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
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Hydrocarbon derivative
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	1.79	ALOGPS
logP	1.93	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.7 m³·mol⁻¹	ChemAxon
Polarizability	47.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0040721

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020529

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

75051748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0206814)

MOL for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

PDB for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

Structure for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0206814 ({3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)