NP-MRD: Showing NP-Card for beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose (NP0049257)

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Record Information

Version

2.0

Created at

2022-03-17 21:09:35 UTC

Updated at

2022-03-17 21:09:35 UTC

NP-MRD ID

NP0049257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose

Description

Panose belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Panose is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose is found in Melilotus officinalis. Formed by the transferase action on lactose of the b-galactosidases from Saccharomyces fragilis, Aspergillus flavus and Penicillium chrysogenum.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307301919572D          

 34 36  0  0  0  0            999 V2000
    0.2112   -0.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -1.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -0.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -2.3831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -1.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -3.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -3.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -4.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -4.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257   -6.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -6.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -4.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0756   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0756   -5.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -6.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -7.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -3.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -6.9206    0.0000 O   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  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 15 14  1  0  0  0  0
 14 16  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 24 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 27 31  1  0  0  0  0
 26 32  1  0  0  0  0
 25 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END


  Mrv1652307301919572D          

 34 36  0  0  0  0            999 V2000
    0.2112   -0.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -1.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -0.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -2.3831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -1.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -3.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -3.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -4.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -4.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257   -6.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -6.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -4.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0756   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0756   -5.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -6.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6467   -7.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611   -3.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -4.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -6.9206    0.0000 O   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  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 15 14  1  0  0  0  0
 14 16  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 24 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 27 31  1  0  0  0  0
 26 32  1  0  0  0  0
 25 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2OC(OC3C(O)C(O)C(O)OC3CO)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O16/c19-1-4-7(21)9(23)13(27)17(32-4)30-3-6-8(22)10(24)14(28)18(33-6)34-15-5(2-20)31-16(29)12(26)11(15)25/h4-29H,1-3H2

> <INCHI_KEY>
OWEGMIWEEQEYGQ-UHFFFAOYSA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.4371

> <EXACT_MASS>
504.169034976

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.53009967638786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxane-2,3,4-triol

> <JCHEM_LOGP>
-6.474210509333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.962799798441964

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.215584174385581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486682235600147

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
100.74999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxane-2,3,4-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       0.394  -1.368   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.939  -2.138   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.273  -1.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.607  -2.138   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.607  -3.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.273  -4.448   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.394   0.172   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.273   0.172   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.941  -1.368   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.941  -4.448   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.939  -3.678   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.273  -5.988   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.939  -6.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.939  -8.298   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.273  -9.068   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.394  -9.068   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.394 -10.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.939 -11.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.273 -10.608   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.728 -11.378   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.728  -8.298   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.607 -11.378   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.941 -10.608   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.274 -11.378   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.941  -9.068   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.274  -8.298   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.608  -9.068   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -7.608 -10.608   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.274 -12.918   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.941 -13.688   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.942  -8.298   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.274  -6.758   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -3.607  -8.298   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.939 -12.918   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5   11   12                                                  
CONECT    7    1                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    2    6                                                       
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   19   14                                                       
CONECT   16   17   14   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   15   22                                                  
CONECT   20   17                                                            
CONECT   21   16                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   28   23   29                                                  
CONECT   25   26   23   33                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   24                                                       
CONECT   29   24   30                                                       
CONECT   30   29                                                            
CONECT   31   27                                                            
CONECT   32   26                                                            
CONECT   33   25                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-a-Isomaltosylglucose	HMDB
alpha-D-GLCP-(1->6)-alpha-D-GLCP-(1->4)-D-GLCP	HMDB
O-a-D-Glucopyranosyl-(1->6)-O-a-D-glucopyranosyl-(1->4)-D-glucose, 9ci	HMDB

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4371 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxane-2,3,4-triol

Traditional Name

6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxane-2,3,4-triol

CAS Registry Number

61237-56-7

SMILES

OCC1OC(OCC2OC(OC3C(O)C(O)C(O)OC3CO)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C18H32O16/c19-1-4-7(21)9(23)13(27)17(32-4)30-3-6-8(22)10(24)14(28)18(33-6)34-15-5(2-20)31-16(29)12(26)11(15)25/h4-29H,1-3H2

InChI Key

OWEGMIWEEQEYGQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Melilotus officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-13556 )

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	-6.5	ChemAxon
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	46.53 Å³	ChemAxon
Number of Rings	3	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

HMDB0029937

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019339

KNApSAcK ID

Not Available

Chemspider ID

3333356

KEGG Compound ID

C00713

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

PANOSE

METLIN ID

Not Available

PubChem Compound

4120027

PDB ID

Not Available

ChEBI ID

7912

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose (NP0049257)

MOL for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

3D MOL for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

3D SDF for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

3D-SDF for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

PDB for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

3D PDB for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

SMILES for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

INCHI for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

Structure for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)

3D Structure for NP0049257 (beta-D-Glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->4)-D-mannose)