NP-MRD: Showing NP-Card for 2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol (NP0325527)

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Record Information

Version

2.0

Created at

2022-09-12 06:20:45 UTC

Updated at

2022-09-12 06:20:45 UTC

NP-MRD ID

NP0325527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

Description

2-(3-Hydroxyphenyl)ethanol 1'-glucoside belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 2-(3-Hydroxyphenyl)ethanol 1'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(3-Hydroxyphenyl)ethanol 1'-glucoside has been detected, but not quantified in, fruits. 2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol is found in Sambucus nigra. This could make 2-(3-hydroxyphenyl)ethanol 1'-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -5.3560    1.4481    0.3076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381    1.9904   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901    0.8756   -0.6827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0677    1.2740   -1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    0.3388   -0.9384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0052    0.7314   -1.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    0.9273   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -0.3196   -0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352   -0.1262    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2100   -0.3150   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -0.1435    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    0.2258    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3882    0.4188    2.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861    0.7907    3.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    0.2459    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682   -0.9830   -1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7519   -1.9051   -1.8255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -1.4613   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6798   -1.9467    0.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -0.2882    0.2721 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5629   -0.6900    0.5955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    1.5668    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321    2.5149    0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3843    2.7582   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663    0.5089   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7608    0.2437    0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046    1.7187   -0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431    1.3832   -1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -1.1011   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.6672    0.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -0.6097   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782   -0.2912   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    0.3617    1.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579    0.9230    3.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    0.3998    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.7968   -2.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472   -2.5410   -1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2165   -2.2420   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -2.8709    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    0.0638    1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0390   -0.8365   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 10  9  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  6
  5 26  1  1
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 15 35  1  0
 14 34  1  0
 12 33  1  0
 11 32  1  0
 10 31  1  0
 16 36  1  6
 17 37  1  0
 18 38  1  6
 19 39  1  0
 20 40  1  1
 21 41  1  0
M  END


  Mrv0541 05061310232D          

 21 22  0  0  0  0            999 V2000
    3.5724    3.7125    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    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
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCCC2=CC(O)=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O7/c15-7-10-11(17)12(18)13(19)14(21-10)20-5-4-8-2-1-3-9(16)6-8/h1-3,6,10-19H,4-5,7H2

> <INCHI_KEY>
DIGNKQFJIIKEBA-UHFFFAOYSA-N

> <FORMULA>
C14H20O7

> <MOLECULAR_WEIGHT>
300.3044

> <EXACT_MASS>
300.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.268814981660086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-0.5798437136666671

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.213691663193718

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.053251636213764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083411880946

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
72.0231

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

> <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       6.668   6.930   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   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  18.480   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  13.090   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  13.090   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  15.400   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1    9                                                       
CONECT    4    5    8                                                       
CONECT    5    4   20                                                       
CONECT    6    8    9                                                       
CONECT    7   10   15                                                       
CONECT    8    2    4    6                                                  
CONECT    9    3    6   16                                                  
CONECT   10    7   11   21                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   20   21                                                  
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    5   14                                                       
CONECT   21   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O₇

Average Mass

300.3044 Da

Monoisotopic Mass

300.12090 Da

IUPAC Name

2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1OC(OCCC2=CC(O)=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H20O7/c15-7-10-11(17)12(18)13(19)14(21-10)20-5-4-8-2-1-3-9(16)6-8/h1-3,6,10-19H,4-5,7H2

InChI Key

DIGNKQFJIIKEBA-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
Sambucus nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
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	-1.2	ALOGPS
logP	-0.58	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	30.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038332

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017667

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

75586327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol (NP0325527)

MOL for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D MOL for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D SDF for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D-SDF for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

PDB for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D PDB for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

SMILES for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

INCHI for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

Structure for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D Structure for NP0325527 (2-(hydroxymethyl)-6-[2-(3-hydroxyphenyl)ethoxy]oxane-3,4,5-triol)