NP-MRD: Showing NP-Card for Gaultherin (NP0137519)

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Record Information

Version

2.0

Created at

2022-05-30 16:54:52 UTC

Updated at

2022-05-30 16:54:53 UTC

NP-MRD ID

NP0137519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gaultherin

Description

Gaultherin is found in Gaultheria pyroloides.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533007131513482D          

 40 42  0  0  1  0            999 V2000
    5.0013    3.7125    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
    1.4289    2.4750    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
    1.4289    3.3000    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
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 18 39  1  6  0  0  0
 19 40  1  6  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533007131513482D          

 40 42  0  0  1  0            999 V2000
    5.0013    3.7125    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
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M  END
> <DATABASE_ID>
NP0137519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)CO[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC=CC=C3C(=O)OC)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O12/c1-27-17(26)8-4-2-3-5-10(8)30-19-16(25)14(23)13(22)11(31-19)7-29-18-15(24)12(21)9(20)6-28-18/h2-5,9,11-16,18-25H,6-7H2,1H3/t9-,11-,12+,13-,14+,15-,16-,18+,19-/m1/s1

> <INCHI_KEY>
VHUNCYDAXJGCLO-AHMNSWSSSA-N

> <FORMULA>
C19H26O12

> <MOLECULAR_WEIGHT>
446.405

> <EXACT_MASS>
446.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.242817310768714

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}benzoate

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-1.7354113386666665

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.457133532645344

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.922599605265926

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084756

> <JCHEM_POLAR_SURFACE_AREA>
184.59999999999997

> <JCHEM_REFRACTIVITY>
98.65939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  13.090   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      -0.000  18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  17.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000  15.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.000  20.020   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  18.480   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667  15.400   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334  16.170   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.000  13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      -1.334  19.250   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.000  12.320   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.000  16.940   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.334  10.010   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.334  10.010   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.667  16.940   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.000   7.700   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.334  14.630   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.667   7.700   0.000  0.00  0.00           H+0
CONECT    1   27                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   28                                                       
CONECT    7   11   29                                                       
CONECT    8    4   10   17                                                  
CONECT    9    6   12   20   32                                             
CONECT   10    5    8   30                                                  
CONECT   11    7   13   31   33                                             
CONECT   12    9   15   21   34                                             
CONECT   13   11   14   22   35                                             
CONECT   14   13   16   23   36                                             
CONECT   15   12   18   24   37                                             
CONECT   16   14   19   25   38                                             
CONECT   17    8   26   27                                                  
CONECT   18   15   28   29   39                                             
CONECT   19   16   30   31   40                                             
CONECT   20    9                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27    1   17                                                       
CONECT   28    6   18                                                       
CONECT   29    7   18                                                       
CONECT   30   10   19                                                       
CONECT   31   11   19                                                       
CONECT   32    9                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
Gaultherin	MeSH
2-((6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy) benzoic acid methyl ester	MeSH

Chemical Formula

C₁₉H₂₆O₁₂

Average Mass

446.4050 Da

Monoisotopic Mass

446.14243 Da

IUPAC Name

methyl 2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}benzoate

Traditional Name

methyl 2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}benzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)CO[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC=CC=C3C(=O)OC)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C19H26O12/c1-27-17(26)8-4-2-3-5-10(8)30-19-16(25)14(23)13(22)11(31-19)7-29-18-15(24)12(21)9(20)6-28-18/h2-5,9,11-16,18-25H,6-7H2,1H3/t9-,11-,12+,13-,14+,15-,16-,18+,19-/m1/s1

InChI Key

VHUNCYDAXJGCLO-AHMNSWSSSA-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
Gaultheria pyroloides	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
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
Monocyclic benzene moiety
Benzenoid
Oxane
Methyl ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
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	-1.2	ALOGPS
logP	-1.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.66 m³·mol⁻¹	ChemAxon
Polarizability	42.24 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

FDB007460

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

5315244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gaultherin (NP0137519)

MOL for NP0137519 (Gaultherin)

3D MOL for NP0137519 (Gaultherin)

3D SDF for NP0137519 (Gaultherin)

3D-SDF for NP0137519 (Gaultherin)

PDB for NP0137519 (Gaultherin)

3D PDB for NP0137519 (Gaultherin)

SMILES for NP0137519 (Gaultherin)

INCHI for NP0137519 (Gaultherin)

Structure for NP0137519 (Gaultherin)

3D Structure for NP0137519 (Gaultherin)