NP-MRD: Showing NP-Card for 2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol (NP0328749)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 12:30:51 UTC

Updated at

2022-09-12 12:30:51 UTC

NP-MRD ID

NP0328749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Isosalicin, also known as p-tolunitril or 4-cyanotoluene, 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. Isosalicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isosalicin has been detected, but not quantified in, alcoholic beverages and tea. 2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol is found in Catharanthus roseus, Crepis foetida and Foeniculum vulgare. This could make isosalicin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.3631   -1.7060    2.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -2.0251    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4700   -1.0614   -0.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1539   -0.9070   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4993    0.2933   -0.2209 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3643    0.2864   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6280    0.5353   -1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    0.0545   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7878    0.6497    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8469    0.3095    1.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520   -0.6226    1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737   -1.2342    0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -0.9039   -0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -1.5256   -1.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568    1.5423   -0.2811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4470    1.9980   -1.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.3442    0.2882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4904    2.4734    0.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.0928   -0.2174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8730    0.2595   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972   -2.5577    2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -1.9011    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650   -3.0779    0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -1.6694   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512    0.4078    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8155    1.7139   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.3503   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229    1.3989    1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9646    0.7512    2.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5843   -0.8931    2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3429   -1.9854   -0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216   -2.1924   -2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489    2.3591    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5560    2.1352   -2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    1.1664    1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878    3.2629    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -0.0441    0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4266    0.9222   -2.0433 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 13  8  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  6
  5 25  1  1
  7 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  1
 20 38  1  0
M  END


  Mrv0541 05061307302D          

 20 21  0  0  0  0            999 V2000
    1.4289    3.3000    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    3.7125    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
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
   -2.1434    7.0125    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
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  9  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  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19  6  1  0  0  0  0
 19 13  1  0  0  0  0
 20  9  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2=CC=CC=C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O7/c14-5-9-10(16)11(17)12(18)13(20-9)19-6-7-3-1-2-4-8(7)15/h1-4,9-18H,5-6H2

> <INCHI_KEY>
VBSPBYNZPRRGSB-UHFFFAOYSA-N

> <FORMULA>
C13H18O7

> <MOLECULAR_WEIGHT>
286.2778

> <EXACT_MASS>
286.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.262793971862095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-0.8685049186666667

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.21081066847107

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.116631878957493

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083553670037

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
67.2681

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]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       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  10.780   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  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335  13.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  13.090   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    9   14                                                       
CONECT    6    7   19                                                       
CONECT    7    3    6    8                                                  
CONECT    8    4    7   15                                                  
CONECT    9    5   10   20                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   19   20                                                  
CONECT   14    5                                                            
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    6   13                                                       
CONECT   20    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl-4-cyanobenzene	HMDB
4-Cyanotoluene	HMDB
4-Methyl-benzonitrile	HMDB
4-Methylbenzonitrile	HMDB
4-Methylcyanobenzene	HMDB
4-Toluenkarbonitril	HMDB
4-Tolunitrile	HMDB
Nitril kyseliny p-toluylove	HMDB
p-Cyanotoluene	HMDB
p-Methylbenzonitrile	HMDB
p-Toluenenitrile	HMDB
p-Toluic nitrile	HMDB
p-Tolunitril	HMDB
p-Tolunitrile	HMDB
p-Toluonitrile	HMDB
p-Tolylnitrile	HMDB

Chemical Formula

C₁₃H₁₈O₇

Average Mass

286.2778 Da

Monoisotopic Mass

286.10525 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(OCC2=CC=CC=C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H18O7/c14-5-9-10(16)11(17)12(18)13(20-9)19-6-7-3-1-2-4-8(7)15/h1-4,9-18H,5-6H2

InChI Key

VBSPBYNZPRRGSB-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
Catharanthus roseus	LOTUS Database	35616633
Crepis foetida	LOTUS Database	35616633
Foeniculum vulgare	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	-1.4	ALOGPS
logP	-0.87	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.12	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	4	ChemAxon
Refractivity	67.27 m³·mol⁻¹	ChemAxon
Polarizability	28.26 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

HMDB0034023

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012261

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

12304407

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-hydroxyphenyl)methoxy]oxane-3,4,5-triol (NP0328749)

MOL for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

3D MOL for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

3D SDF for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

3D-SDF for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

PDB for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

3D PDB for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

SMILES for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

INCHI for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

Structure for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)

3D Structure for NP0328749 (2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol)