NP-MRD: Showing NP-Card for Cellobiose (NP0000320)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-04-19 09:27:37 UTC

NP-MRD ID

NP0000320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cellobiose

Description

Cellobiose, also known as GLCB1-4GLCB or cellose, is a disaccharide. It is also classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair beta-glucose molecules creating a beta (1→4) bond. It belongs to the class of organic compounds known as O-glycosyl compounds. These are glycosides in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Cellobiose can be obtained by enzymatic hydrolysis of cellulose and cellulose-rich materials such as cotton, jute, or paper. Cellobiose is a plant metabolite found in flowering plants, conifers and other gymnosperms. Cellobiose can also be found in vertebrates that have consumed plant foods. It has been detected, but not quantified in, several different foods, such as okra, common chokecherries, cherry tomatoes, and welsh onions. Cellobiose can be used as an indicator carbohydrate for Crohn's disease and malabsorption syndrome. Intestinal permeability to detect Crohn's disease and malabsorption syndrome can be measured by the sugar absorption test. This test is based on determining the ratio of the urinary excretion of a large (a disaccharide such as cellobiose) and a small carbohydrate (a monosaccharide such as lactulose or rhamnose) after oral administration. Patients with Crohn's disease or with ulcerative colitis have increased permeability indices in comparison to healthy controls (PMID: 15546811 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000055
     RDKit          3D
Cellobiose
 45 46  0  0  0  0  0  0  0  0999 V2000
    3.3309    3.1106   -0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.8264   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    0.8488    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7562    0.8385   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -0.2167    0.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1979   -0.0650   -0.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138   -0.0324    0.0976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3925   -1.0811   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4082   -1.2915    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.4531    2.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.9226   -1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    0.3317   -2.0113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2614    0.4426   -2.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    1.4377   -1.0125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9913    2.6448   -1.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168    1.3719   -0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4856    1.8336    1.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306   -1.4808   -0.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8482   -2.5948   -0.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418   -1.6433    0.9002 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475   -2.8135    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388   -0.4631    0.7581 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5355   -0.3776    1.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    3.0330   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8652    1.8300    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.5422   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.2495    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.3039    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.1527    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -2.0566   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870   -2.2225    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.4180    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -0.5860    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537    0.5154   -2.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0264    0.0279   -2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1369    1.4818   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    2.5053   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858    2.0742   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4736    1.8776    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -1.2419   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3267   -3.2725   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -1.6460    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -2.6026    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2701   -0.6041   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -1.2810    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 16  7  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  1
  5 28  1  1
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END

Cellobiose.mol
  Mrv1652303182019232D          

 23 24  0  0  0  0            999 V2000
    0.8250    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 10 23  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1

> <INCHI_KEY>
GUBGYTABKSRVRQ-QRZGKKJRSA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.2965

> <EXACT_MASS>
342.116211546

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.080234566711404

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.01

> <JCHEM_LOGP>
-4.703374863666666

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.173689317234608

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.254374125721942

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835652988272

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.3367

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-cellobiose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000055
     RDKit          3D
Cellobiose
 45 46  0  0  0  0  0  0  0  0999 V2000
    3.3309    3.1106   -0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.8264   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    0.8488    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7562    0.8385   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -0.2167    0.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1979   -0.0650   -0.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138   -0.0324    0.0976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3925   -1.0811   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4082   -1.2915    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.4531    2.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.9226   -1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    0.3317   -2.0113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2614    0.4426   -2.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    1.4377   -1.0125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9913    2.6448   -1.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168    1.3719   -0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4856    1.8336    1.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306   -1.4808   -0.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8482   -2.5948   -0.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418   -1.6433    0.9002 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475   -2.8135    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388   -0.4631    0.7581 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5355   -0.3776    1.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    3.0330   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8652    1.8300    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.5422   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.2495    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.3039    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.1527    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -2.0566   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870   -2.2225    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.4180    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -0.5860    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537    0.5154   -2.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0264    0.0279   -2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1369    1.4818   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    2.5053   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858    2.0742   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4736    1.8776    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -1.2419   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3267   -3.2725   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -1.6460    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -2.6026    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2701   -0.6041   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -1.2810    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 16  7  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  1
  5 28  1  1
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Cellobiose.mol                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  O   UNK     0       1.540   5.335   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.770   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.390   1.334   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.770  -1.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.540  -5.335   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.390  -1.334   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.850   1.334   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.770   1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21                                                            
CONECT   23   10    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0000055
HETATM    1  O1  UNL     1       3.331   3.111  -0.057  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.868   1.826  -0.036  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.923   0.849   0.659  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.756   0.839  -0.026  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.901  -0.217   0.253  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.198  -0.065  -0.552  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.414  -0.032   0.098  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.392  -1.081  -0.296  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.408  -1.291   0.828  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.769  -1.453   2.052  1.00  0.00           O  
HETATM   11  O5  UNL     1      -2.989  -0.923  -1.510  1.00  0.00           O  
HETATM   12  C7  UNL     1      -3.103   0.332  -2.011  1.00  0.00           C  
HETATM   13  O6  UNL     1      -4.261   0.443  -2.795  1.00  0.00           O  
HETATM   14  C8  UNL     1      -3.117   1.438  -1.012  1.00  0.00           C  
HETATM   15  O7  UNL     1      -2.991   2.645  -1.714  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.017   1.372  -0.007  1.00  0.00           C  
HETATM   17  O8  UNL     1      -2.486   1.834   1.209  1.00  0.00           O  
HETATM   18  C10 UNL     1       1.631  -1.481  -0.145  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.848  -2.595  -0.241  1.00  0.00           O  
HETATM   20  C11 UNL     1       2.742  -1.643   0.900  1.00  0.00           C  
HETATM   21  O10 UNL     1       3.447  -2.813   0.701  1.00  0.00           O  
HETATM   22  C12 UNL     1       3.639  -0.463   0.758  1.00  0.00           C  
HETATM   23  O11 UNL     1       4.535  -0.378   1.844  1.00  0.00           O  
HETATM   24  H1  UNL     1       2.385   3.033  -0.301  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.865   1.830   0.447  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.042   1.542  -1.096  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.804   1.249   1.696  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.671  -0.304   1.333  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.202  -0.153   1.187  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.832  -2.057  -0.337  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.987  -2.222   0.648  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.084  -0.418   0.922  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.713  -0.586   2.487  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.254   0.515  -2.723  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.026   0.028  -2.299  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.137   1.482  -0.542  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.578   2.505  -2.606  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.186   2.074  -0.302  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.474   1.878   1.266  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.178  -1.242  -1.097  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.327  -3.273  -0.764  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.259  -1.646   1.910  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.354  -2.603   0.402  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.270  -0.604  -0.142  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.841  -1.281   2.121  1.00  0.00           H  
CONECT    1    2   24
CONECT    2    3   25   26
CONECT    3    4   22   27
CONECT    4    5
CONECT    5    6   18   28
CONECT    6    7
CONECT    7    8   16   29
CONECT    8    9   11   30
CONECT    9   10   31   32
CONECT   10   33
CONECT   11   12
CONECT   12   13   14   34
CONECT   13   35
CONECT   14   15   16   36
CONECT   15   37
CONECT   16   17   38
CONECT   17   39
CONECT   18   19   20   40
CONECT   19   41
CONECT   20   21   22   42
CONECT   21   43
CONECT   22   23   44
CONECT   23   45
END

HMDB0000055
     RDKit          3D
Cellobiose
 45 46  0  0  0  0  0  0  0  0999 V2000
    3.3309    3.1106   -0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.8264   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    0.8488    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7562    0.8385   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -0.2167    0.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1979   -0.0650   -0.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138   -0.0324    0.0976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3925   -1.0811   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4082   -1.2915    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688   -1.4531    2.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.9226   -1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    0.3317   -2.0113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2614    0.4426   -2.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    1.4377   -1.0125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9913    2.6448   -1.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168    1.3719   -0.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4856    1.8336    1.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306   -1.4808   -0.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8482   -2.5948   -0.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418   -1.6433    0.9002 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475   -2.8135    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388   -0.4631    0.7581 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5355   -0.3776    1.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    3.0330   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8652    1.8300    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.5422   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.2495    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.3039    1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.1527    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -2.0566   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870   -2.2225    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.4180    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -0.5860    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537    0.5154   -2.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0264    0.0279   -2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1369    1.4818   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    2.5053   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858    2.0742   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4736    1.8776    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -1.2419   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3267   -3.2725   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -1.6460    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -2.6026    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2701   -0.6041   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -1.2810    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 16  7  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  1
  5 28  1  1
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
1-beta-D-Glucopyranosyl-4-beta-D-glucopyranose	ChEBI
4-O-beta-D-Glucopyranosyl-beta-D-glucopyranose	ChEBI
beta-D-GLC-(1->4)-beta-D-GLC	ChEBI
beta-D-GLCP-(1->4)-beta-D-GLCP	ChEBI
beta-D-Glucosyl-(1->4)-beta-D-glucose	ChEBI
GLCB1-4GLCB	ChEBI
Glcbeta1-4glcbeta	ChEBI
1-b-D-Glucopyranosyl-4-b-D-glucopyranose	Generator
1-Β-D-glucopyranosyl-4-β-D-glucopyranose	Generator
4-O-b-D-Glucopyranosyl-b-D-glucopyranose	Generator
4-O-Β-D-glucopyranosyl-β-D-glucopyranose	Generator
b-D-GLC-(1->4)-b-D-GLC	Generator
Β-D-GLC-(1->4)-β-D-GLC	Generator
b-D-GLCP-(1->4)-b-D-GLCP	Generator
Β-D-GLCP-(1->4)-β-D-GLCP	Generator
b-D-Glucosyl-(1->4)-b-D-glucose	Generator
Β-D-glucosyl-(1->4)-β-D-glucose	Generator
4-(b-D-Glucosido)-D-glucose	HMDB
4-(b-delta-Glucosido)-delta-glucose	HMDB
4-(beta-D-Glucosido)-D-glucose	HMDB
4-(beta-delta-Glucosido)-delta-glucose	HMDB
4-beta-D-Glucopyranosyl-D-glucopyranose	HMDB
4-beta-delta-Glucopyranosyl-delta-glucopyranose	HMDB
4-O-b-D-Glucopyranosyl-D-glucose	HMDB
4-O-beta-D-Glucopyranosyl-D-glucose	HMDB
4-O-beta-delta-Glucopyranosyl-delta-glucose	HMDB
Cellose	HMDB
D-(+)-Cellobiose	HMDB
D-Cellobiose	HMDB
D-Glucosyl-b-(1->4)-D-glucose	HMDB
D-Glucosyl-beta-(1-4)-D-glucose	HMDB
D-Glucosyl-beta-(1->4)-D-glucose	HMDB
delta-(+)-Cellobiose	HMDB
delta-Cellobiose	HMDB
delta-Glucosyl-beta-(1-4)-delta-glucose	HMDB
delta-Glucosyl-beta-(1->4)-delta-glucose	HMDB
4 O beta D Glucopyranosyl D glucopyranose	HMDB
4-O-beta-D-Glucopyranosyl-D-glucopyranose	HMDB
b-Cellobiose	HMDB
Β-cellobiose	HMDB
CELLOBIOSE	ChEBI

Chemical Formula

C₁₂H₂₂O₁₁

Average Mass

342.2965 Da

Monoisotopic Mass

342.11621 Da

IUPAC Name

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

Traditional Name

β-cellobiose

CAS Registry Number

528-50-7

SMILES

OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1

InChI Key

GUBGYTABKSRVRQ-QRZGKKJRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona muricata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arabidopsis thaliana	Plant	KNApSAcK
Averrhoa carambola	Plant	KNApSAcK
Brassica oleracea L. ssp. Botrytis	Plant	KNApSAcK
Capsicum annuum	Plant	KNApSAcK
Cassia multijuga	Plant	KNApSAcK
Daphnia pulex	LOTUS Database	35616633
Forsythia spp.	Plant	KNApSAcK
Forsythia suspensa	Plant	KNApSAcK
Haemodorum corymbosum	Plant	KNApSAcK
Homo sapiens (Urine)	Animalia	KNApSAcK
Litoria verreauxii	LOTUS Database	35616633
Manilkara zapota	Plant	KNApSAcK
Medicago sativa	Plant	KNApSAcK
Nigella sativa	LOTUS Database	35616633
Oryza sativa	Plant	KNApSAcK
Panax ginseng	Plant	KNApSAcK
Paris polyphylla	LOTUS Database	35616633
Prunus avium	Plant	KNApSAcK
Solanum lycopersicum	Plant	KNApSAcK
Triticum aestivum	Plant	KNApSAcK
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Disaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

cellobiose (CHEBI:36217 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	229 - 230 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	111 mg/mL at 15 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	586 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.08 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cellobiose

METLIN ID

3480

PubChem Compound

10712

PDB ID

Not Available

ChEBI ID

36217

Good Scents ID

rw1233711

References

General References

Morita T, Ozawa M, Ito H, Kimio S, Kiriyama S: Cellobiose is extensively digested in the small intestine by beta-galactosidase in rats. Nutrition. 2008 Nov-Dec;24(11-12):1199-204. doi: 10.1016/j.nut.2008.06.029. Epub 2008 Aug 26. [PubMed:18752931 ]
Matsuura Y: Degradation of konjac glucomannan by enzymes in human feces and formation of short-chain fatty acids by intestinal anaerobic bacteria. J Nutr Sci Vitaminol (Tokyo). 1998 Jun;44(3):423-36. [PubMed:9742462 ]
Nakamura S, Oku T, Ichinose M: Bioavailability of cellobiose by tolerance test and breath hydrogen excretion in humans. Nutrition. 2004 Nov-Dec;20(11-12):979-83. [PubMed:15561487 ]
Cain WJ, Millar JS, Himebauch AS, Tietge UJ, Maugeais C, Usher D, Rader DJ: Lipoprotein [a] is cleared from the plasma primarily by the liver in a process mediated by apolipoprotein [a]. J Lipid Res. 2005 Dec;46(12):2681-91. Epub 2005 Sep 8. [PubMed:16150825 ]
Cobden I, Hamilton I, Rothwell J, Axon AT: Cellobiose/mannitol test: physiological properties of probe molecules and influence of extraneous factors. Clin Chim Acta. 1985 May 15;148(1):53-62. [PubMed:3924445 ]
Welcker K, Martin A, Kolle P, Siebeck M, Gross M: Increased intestinal permeability in patients with inflammatory bowel disease. Eur J Med Res. 2004 Oct 29;9(10):456-60. [PubMed:15546811 ]
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Showing NP-Card for Cellobiose (NP0000320)

MOL for NP0000320 (Cellobiose)

3D MOL for NP0000320 (Cellobiose)

3D SDF for NP0000320 (Cellobiose)

3D-SDF for NP0000320 (Cellobiose)

PDB for NP0000320 (Cellobiose)

3D PDB for NP0000320 (Cellobiose)

SMILES for NP0000320 (Cellobiose)

INCHI for NP0000320 (Cellobiose)

Structure for NP0000320 (Cellobiose)

3D Structure for NP0000320 (Cellobiose)