NP-MRD: Showing NP-Card for (-)-Methyl beta-D-fructofuranoside (NP0078606)

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Record Information

Version

2.0

Created at

2022-04-28 23:39:13 UTC

Updated at

2022-04-28 23:39:13 UTC

NP-MRD ID

NP0078606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Methyl beta-D-fructofuranoside

Description

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol belongs to the class of organic compounds known as c-glycosyl compounds. (-)-Methyl beta-D-fructofuranoside is found in Alisma plantago-aquatica, Artemisia monosperma, Brachystemma calycinum, Coriandrum sativum, Lilium tenuifolium, Morinda citrifolia , Ophiopogon japonicus, Turnera diffusa and Vaccinium myrtillus. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308061607422D          

 16 16  0  0  1  0            999 V2000
   -0.9067   -1.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517   -0.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643    1.4442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6830    0.0460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  1  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  6  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  5 10  1  6  0  0  0
  6 11  1  1  0  0  0
 12  1  1  0  0  0  0
  7 12  1  1  0  0  0
 13  4  1  0  0  0  0
 13  7  1  0  0  0  0
  4 14  1  6  0  0  0
  5 15  1  1  0  0  0
  6 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078606

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O6/c1-12-7(3-9)6(11)5(10)4(2-8)13-7/h4-6,8-11H,2-3H2,1H3/t4-,5-,6+,7-/m1/s1

> <INCHI_KEY>
JPHVNZOOBXUCDJ-MVIOUDGNSA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.183

> <EXACT_MASS>
194.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.235544778986608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol

> <ALOGPS_LOGP>
-2.01

> <JCHEM_LOGP>
-2.1148728143333333

> <ALOGPS_LOGS>
0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.394406658049533

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.09067258776722

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9814325619371136

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
41.112

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-AUG-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-AUG-16         0                                  
HETATM    1  C   UNK     0      -1.692  -2.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.451  -1.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.091   3.157   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.858  -2.448   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.217  -0.610   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.547   2.696   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.312   2.779   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.275   0.086   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2    4    8                                                       
CONECT    3    7    9                                                       
CONECT    4    2    5   13   14                                             
CONECT    5    4    6   10   15                                             
CONECT    6    5    7   11   16                                             
CONECT    7    3    6   12   13                                             
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    1    7                                                       
CONECT   13    4    7                                                       
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(alpha-D)-Isomer OF methylfructoside	MeSH
1-O-Methylfructofuranose	MeSH
Methyl-alpha-D-fructofuranoside	MeSH
Methyl-beta-D-fructofuranoside	MeSH
Methyl-beta-D-fructoside	MeSH
Methylfructoside	MeSH

Chemical Formula

C₇H₁₄O₆

Average Mass

194.1830 Da

Monoisotopic Mass

194.07904 Da

IUPAC Name

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol

Traditional Name

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)[C@@]([H])(CO)O[C@@](CO)(OC)[C@@]1([H])O

InChI Identifier

InChI=1S/C7H14O6/c1-12-7(3-9)6(11)5(10)4(2-8)13-7/h4-6,8-11H,2-3H2,1H3/t4-,5-,6+,7-/m1/s1

InChI Key

JPHVNZOOBXUCDJ-MVIOUDGNSA-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
Alisma plantago-aquatica	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Brachystemma calycinum	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Lilium tenuifolium	LOTUS Database	35616633
Morinda citrifolia	Plant	KNApSAcK
Ophiopogon japonicus	LOTUS Database	35616633
Turnera diffusa	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Ketal
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Primary alcohol
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	ALOGPS
logP	-2.1	ChemAxon
logS	0.77	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	41.11 m³·mol⁻¹	ChemAxon
Polarizability	18.24 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

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

128889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Methyl beta-D-fructofuranoside (NP0078606)

MOL for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

3D MOL for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

3D SDF for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

3D-SDF for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

PDB for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

3D PDB for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

SMILES for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

INCHI for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

Structure for NP0078606 ((-)-Methyl beta-D-fructofuranoside)

3D Structure for NP0078606 ((-)-Methyl beta-D-fructofuranoside)