NP-MRD: Showing NP-Card for o1-methyl-glucose (NP0286342)

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Record Information

Version

2.0

Created at

2022-09-09 14:52:29 UTC

Updated at

2022-09-09 14:52:30 UTC

NP-MRD ID

NP0286342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

o1-methyl-glucose

Description

Methyl beta-D-glucopyranoside, also known as Beta-methyl-D-glucoside or methyl hexopyranoside, 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. o1-methyl-glucose is found in Cheiraster dawsoni, Euterpe precatoria, Osmanthus fortunei, Paxillus involutus, Pedicularis plicata, Phlomoides tuberosa and Rosa laevigata. o1-methyl-glucose was first documented in 1997 (PMID: 11671987). Methyl beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 17929936) (PMID: 19630436).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307191923592D          

 13 13  0  0  0  0            999 V2000
 9984.9675 9984.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.1098 9984.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.9676 9983.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.5393 9982.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.1101 9983.0302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.2533 9984.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.2533 9983.4423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.5388 9983.0298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9982.8244 9983.4423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.8243 9984.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9983.5388 9984.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.9674 9985.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.3964 9984.2692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 10 11  1  0  0  0  0
  6  1  1  1  0  0  0
 10  2  1  1  0  0  0
  9  5  1  6  0  0  0
  8  4  1  1  0  0  0
  7  3  1  6  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286342

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7-/m1/s1

> <INCHI_KEY>
HOVAGTYPODGVJG-XUUWZHRGSA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.1825

> <EXACT_MASS>
194.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.29565252029707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.49

> <JCHEM_LOGP>
-2.2894127143333334

> <ALOGPS_LOGS>
0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200415670112982

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21139322915757

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083281156967

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
40.67459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl β-d-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  O   UNK     0    8638.6068638.069   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8633.2728638.071   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8638.6068634.989   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8635.9408633.450   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8633.2728634.990   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8637.2738637.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8637.2738635.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8635.9398634.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8634.6068635.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8634.6058637.299   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8635.9398638.069   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8638.6068639.609   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8631.9408637.303   0.000  0.00  0.00           O+0
CONECT    1    6   12                                                       
CONECT    2   10   13                                                       
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    9                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8    3                                                  
CONECT    8    7    9    4                                                  
CONECT    9    8   10    5                                                  
CONECT   10    9   11    2                                                  
CONECT   11    6   10                                                       
CONECT   12    1                                                            
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
1-O-Methyl-beta-D-glucopyranoside	ChEBI
beta-D-Methylglucopyranoside	ChEBI
Beta-Methyl-D-glucoside	ChEBI
beta-Methylglucoside	ChEBI
Methyl beta-D-glucoside	ChEBI
Methyl hexopyranoside	ChEBI
1-O-Methyl-b-D-glucopyranoside	Generator
1-O-Methyl-β-D-glucopyranoside	Generator
b-D-Methylglucopyranoside	Generator
Β-D-methylglucopyranoside	Generator
b-Methyl-D-glucoside	Generator
Β-methyl-D-glucoside	Generator
b-Methylglucoside	Generator
Β-methylglucoside	Generator
Methyl b-D-glucoside	Generator
Methyl β-D-glucoside	Generator
Methyl b-D-glucopyranoside	Generator
Methyl β-D-glucopyranoside	Generator
Methyl D-glucopyranoside	HMDB
Methyl D-glucoside	HMDB
Methylglucoside	HMDB
Methylglucoside, (beta-D)-isomer	HMDB
1-O-Methylglucose	HMDB
D-Glucoside, methyl	HMDB
Methyl glucose	HMDB
Methyl-D-glucoside	HMDB

Chemical Formula

C₇H₁₄O₆

Average Mass

194.1825 Da

Monoisotopic Mass

194.07904 Da

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

Traditional Name

methyl β-d-glucoside

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7-/m1/s1

InChI Key

HOVAGTYPODGVJG-XUUWZHRGSA-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
Cheiraster dawsoni	LOTUS Database	35616633
Euterpe precatoria	LOTUS Database	35616633
Osmanthus fortunei	LOTUS Database	35616633
Paxillus involutus	LOTUS Database	35616633
Pedicularis plicata	LOTUS Database	35616633
Phlomoides tuberosa	LOTUS Database	35616633
Rosa laevigata	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
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:320055 )
methyl D-glucoside (CHEBI:320055 )

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	ALOGPS
logP	-2.3	ChemAxon
logS	0.65	ALOGPS
pKa (Strongest Acidic)	12.21	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	2	ChemAxon
Refractivity	40.67 m³·mol⁻¹	ChemAxon
Polarizability	18.3 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

HMDB0029965

DrugBank ID

DB01642

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

445238

PDB ID

Not Available

ChEBI ID

320055

Good Scents ID

Not Available

References

General References

Bhattarai KM, Davis AP, Perry JJ, Walter CJ, Menzer S, Williams DJ: A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility. J Org Chem. 1997 Nov 28;62(24):8463-8473. doi: 10.1021/jo971272w. [PubMed:11671987 ]
Cheng G, Fan R, Hernandez-Torres JM, Boulineau FP, Wei A: syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides. Org Lett. 2007 Nov 8;9(23):4849-52. doi: 10.1021/ol702185y. Epub 2007 Oct 12. [PubMed:17929936 ]
Hosoya T, Nakao Y, Sato H, Kawamoto H, Sakaki S: Thermal degradation of methyl beta-D-glucoside. a theoretical study of plausible reaction mechanisms. J Org Chem. 2009 Sep 4;74(17):6891-4. doi: 10.1021/jo900457k. [PubMed:19630436 ]
LOTUS database [Link]

Showing NP-Card for o1-methyl-glucose (NP0286342)

MOL for NP0286342 (o1-methyl-glucose)

3D MOL for NP0286342 (o1-methyl-glucose)

3D SDF for NP0286342 (o1-methyl-glucose)

3D-SDF for NP0286342 (o1-methyl-glucose)

PDB for NP0286342 (o1-methyl-glucose)

3D PDB for NP0286342 (o1-methyl-glucose)

SMILES for NP0286342 (o1-methyl-glucose)

INCHI for NP0286342 (o1-methyl-glucose)

Structure for NP0286342 (o1-methyl-glucose)

3D Structure for NP0286342 (o1-methyl-glucose)