NP-MRD: Showing NP-Card for (-)-Foliachinenoside A1 (NP0071219)

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Record Information

Version

2.0

Created at

2022-04-28 16:36:25 UTC

Updated at

2022-04-28 16:36:25 UTC

NP-MRD ID

NP0071219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Foliachinenoside A1

Description

2,6-Bis(beta-D-glucopyranosyloxy)benzoic acid benzyl ester 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. (-)-Foliachinenoside A1 is found in Salacia chinensis and Salacia chinensis LINN. . Based on a literature review very few articles have been published on 2,6-Bis(beta-D-glucopyranosyloxy)benzoic acid benzyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218362D          

 40 43  0  0  1  0            999 V2000
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   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282218362D          

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   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 22 25  1  1  0  0  0
 21 26  1  6  0  0  0
 20 27  1  1  0  0  0
 27 28  1  0  0  0  0
  1 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  1  0  0  0
 36 37  1  0  0  0  0
 33 38  1  6  0  0  0
 32 39  1  1  0  0  0
 31 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0071219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2C(=O)OCC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O14/c27-9-15-18(29)20(31)22(33)25(39-15)37-13-7-4-8-14(17(13)24(35)36-11-12-5-2-1-3-6-12)38-26-23(34)21(32)19(30)16(10-28)40-26/h1-8,15-16,18-23,25-34H,9-11H2/t15-,16-,18-,19-,20+,21+,22-,23-,25-,26-/m1/s1

> <INCHI_KEY>
NDRNJZCDLHNMRR-NXEOTYAVSA-N

> <FORMULA>
C26H32O14

> <MOLECULAR_WEIGHT>
568.528

> <EXACT_MASS>
568.17920571

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.92302808191051

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-1.4420709326666665

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.421282071893621

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.899077407545116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346304199

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
130.9465

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.27e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+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 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    5   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   21                                                            
CONECT   27   20   28                                                       
CONECT   28   27                                                            
CONECT   29    1   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   40                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   33                                                            
CONECT   39   32                                                            
CONECT   40   31                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
2,6-Bis(b-D-glucopyranosyloxy)benzoate benzyl ester	Generator
2,6-Bis(b-D-glucopyranosyloxy)benzoic acid benzyl ester	Generator
2,6-Bis(beta-D-glucopyranosyloxy)benzoate benzyl ester	Generator
2,6-Bis(β-D-glucopyranosyloxy)benzoate benzyl ester	Generator
2,6-Bis(β-D-glucopyranosyloxy)benzoic acid benzyl ester	Generator

Chemical Formula

C₂₆H₃₂O₁₄

Average Mass

568.5280 Da

Monoisotopic Mass

568.17921 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2C(=O)OCC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H32O14/c27-9-15-18(29)20(31)22(33)25(39-15)37-13-7-4-8-14(17(13)24(35)36-11-12-5-2-1-3-6-12)38-26-23(34)21(32)19(30)16(10-28)40-26/h1-8,15-16,18-23,25-34H,9-11H2/t15-,16-,18-,19-,20+,21+,22-,23-,25-,26-/m1/s1

InChI Key

NDRNJZCDLHNMRR-NXEOTYAVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Salacia chinensis	LOTUS Database	35616633
Salacia chinensis LINN.	Plant	KNApSAcK

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
Hexose monosaccharide
O-glycosyl compound
Benzoate ester
Benzyloxycarbonyl
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
Sugar acid
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
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	-0.53	ALOGPS
logP	-1.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.95 m³·mol⁻¹	ChemAxon
Polarizability	54.92 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

101857079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Foliachinenoside A1 (NP0071219)

MOL for NP0071219 ((-)-Foliachinenoside A1)

3D MOL for NP0071219 ((-)-Foliachinenoside A1)

3D SDF for NP0071219 ((-)-Foliachinenoside A1)

3D-SDF for NP0071219 ((-)-Foliachinenoside A1)

PDB for NP0071219 ((-)-Foliachinenoside A1)

3D PDB for NP0071219 ((-)-Foliachinenoside A1)

SMILES for NP0071219 ((-)-Foliachinenoside A1)

INCHI for NP0071219 ((-)-Foliachinenoside A1)

Structure for NP0071219 ((-)-Foliachinenoside A1)

3D Structure for NP0071219 ((-)-Foliachinenoside A1)