NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate (NP0294156)

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Record Information

Version

2.0

Created at

2022-09-10 02:34:05 UTC

Updated at

2022-09-10 02:34:06 UTC

NP-MRD ID

NP0294156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate

Description

Alpha-D-Glucopyranose 6-acetate, also known as a-D-glucopyranose 6-acetic acid, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. [(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate is found in Ligularia atroviolacea. Based on a literature review very few articles have been published on alpha-D-Glucopyranose 6-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    4.3801    0.6842   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    0.4716    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    1.4871    0.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060   -0.7223    0.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808   -1.1684    0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234   -0.9263    0.2526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8752   -1.4504    1.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.2187    0.9922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7596   -1.8837   -0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849    0.2807    0.7787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8508    0.4260    0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329    0.6052   -0.4898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9686    1.9013   -0.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    0.4676   -0.1143 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4988    0.8750   -1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393    0.3280   -0.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5336    1.7298   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3838    0.0780   -1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4439   -2.3013    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2887   -0.8422    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -1.5887   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -1.5626    1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -2.6503   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575    0.8072    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0520    1.3979    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344   -0.1619   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492    1.8919   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.1684    0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    1.8769   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  6
  8 22  1  1
  9 23  1  0
 10 24  1  1
 11 25  1  0
 12 26  1  6
 13 27  1  0
 14 28  1  1
 15 29  1  0
M  END


  Mrv1652309102204342D          

 15 15  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0294156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O7/c1-3(9)14-2-4-5(10)6(11)7(12)8(13)15-4/h4-8,10-13H,2H2,1H3/t4-,5-,6+,7-,8+/m1/s1

> <INCHI_KEY>
ILLOJQCWUBEHBA-CBQIKETKSA-N

> <FORMULA>
C8H14O7

> <MOLECULAR_WEIGHT>
222.193

> <EXACT_MASS>
222.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.22196255667553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate

> <JCHEM_LOGP>
-2.4914138076666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.692124801235117

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.298285667359973

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64907625178777

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
45.07489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
a-D-Glucopyranose 6-acetate	Generator
a-D-Glucopyranose 6-acetic acid	Generator
alpha-D-Glucopyranose 6-acetic acid	Generator
Α-D-glucopyranose 6-acetate	Generator
Α-D-glucopyranose 6-acetic acid	Generator

Chemical Formula

C₈H₁₄O₇

Average Mass

222.1930 Da

Monoisotopic Mass

222.07395 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C8H14O7/c1-3(9)14-2-4-5(10)6(11)7(12)8(13)15-4/h4-8,10-13H,2H2,1H3/t4-,5-,6+,7-,8+/m1/s1

InChI Key

ILLOJQCWUBEHBA-CBQIKETKSA-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
Ligularia atroviolacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Oxane
Monosaccharide
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-2.5	ChemAxon
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.07 m³·mol⁻¹	ChemAxon
Polarizability	20.22 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8618936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10443517

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate (NP0294156)

MOL for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

PDB for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

SMILES for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

INCHI for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

Structure for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0294156 ([(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate)