NP-MRD: Showing NP-Card for n-Decyl-beta-D-Glucopyranoside (NP0331776)

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Record Information

Version

2.0

Created at

2023-08-23 16:01:18 UTC

Updated at

2024-09-03 04:16:53 UTC

NP-MRD ID

NP0331776

Natural Product DOI

https://doi.org/10.57994/0841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-Decyl-beta-D-Glucopyranoside

Description

(2R,3R,4S,5S,6R)-2-(decyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol (2R,3R,4S,5S,6R)-2-(decyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004221604072D          

 27 27  0  0  1  0            999 V2000
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    9.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    9.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  1  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  6  0  0  0
 15 20  1  6  0  0  0
 21 10  1  0  0  0  0
 16 21  1  1  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
 12 23  1  6  0  0  0
 13 24  1  1  0  0  0
 14 25  1  6  0  0  0
 15 26  1  1  0  0  0
 16 27  1  6  0  0  0
M  END


  Mrv1572004221604072D          

 27 27  0  0  1  0            999 V2000
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    9.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    9.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  1  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  6  0  0  0
 15 20  1  6  0  0  0
 21 10  1  0  0  0  0
 16 21  1  1  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
 12 23  1  6  0  0  0
 13 24  1  1  0  0  0
 14 25  1  6  0  0  0
 15 26  1  1  0  0  0
 16 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0331776

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h12-20H,2-11H2,1H3/t12-,13-,14+,15-,16-/m1/s1

> <INCHI_KEY>
JDRSMPFHFNXQRB-IBEHDNSVSA-N

> <FORMULA>
C16H32O6

> <MOLECULAR_WEIGHT>
320.426

> <EXACT_MASS>
320.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69795464902786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.7018982903333342

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200256715324073

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210987486903665

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834105517934

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
82.1542

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
decyl glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.670  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.673  13.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.339  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.339  15.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.005  16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672  15.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.672  13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      24.006  13.860   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.673  16.170   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      20.005  17.710   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      17.338  16.170   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      17.338  13.090   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      20.005  13.090   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      22.673  14.630   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      21.339  16.940   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      20.005  14.630   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      18.672  16.940   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      17.338  14.630   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   21                                                       
CONECT   11   12   17                                                       
CONECT   12   11   13   22   23                                             
CONECT   13   12   14   18   24                                             
CONECT   14   13   15   19   25                                             
CONECT   15   14   16   20   26                                             
CONECT   16   15   21   22   27                                             
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   10   16                                                       
CONECT   22   12   16                                                       
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
Decyl glucoside	MeSH

Chemical Formula

C₁₆H₃₂O₆

Average Mass

320.4260 Da

Monoisotopic Mass

320.21989 Da

IUPAC Name

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

Traditional Name

decyl glucoside

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H32O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h12-20H,2-11H2,1H3/t12-,13-,14+,15-,16-/m1/s1

InChI Key

JDRSMPFHFNXQRB-IBEHDNSVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
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	2.21	ALOGPS
logP	1.7	ChemAxon
logS	-1.9	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	11	ChemAxon
Refractivity	82.15 m³·mol⁻¹	ChemAxon
Polarizability	36.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

62142

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for n-Decyl-beta-D-Glucopyranoside (NP0331776)

MOL for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

3D MOL for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

3D SDF for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

3D-SDF for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

PDB for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

3D PDB for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

SMILES for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

INCHI for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

Structure for NP0331776 (n-Decyl-beta-D-Glucopyranoside)

3D Structure for NP0331776 (n-Decyl-beta-D-Glucopyranoside)