NP-MRD: Showing NP-Card for Melibiose (NP0000538)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:09 UTC

NP-MRD ID

NP0000538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melibiose

Description

Melibiose is disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans, but can be broken down by gut microflora, such as E. Coli. In fact, E. Coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted to β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestability Melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that can strongly affected the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance. (PMID 17986780 ).

Structure

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

HMDB0000048
     RDKit          3D
Melibiose
 45 46  0  0  0  0  0  0  0  0999 V2000
   -3.3490    2.7694   -0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    1.9634   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    0.6490   -1.2039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3499   -0.1776   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -0.8286    0.0708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1367   -1.7354   -0.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099   -1.5788    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -0.2246    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6257   -0.2581    1.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    0.8990    1.5341 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5229    1.9794    1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2149    0.8833    0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9869    2.0993   -0.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -0.2023   -0.6435 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8497   -1.4181   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386    0.0165   -0.7009 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8830    1.3268   -1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3989   -1.6333    0.4697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0815   -2.9622    0.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -1.5135   -0.6582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5481   -2.2614   -0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240   -0.0163   -0.7489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0203    0.3850    0.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117    2.7768   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763    1.7751    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    2.5033   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    0.9274   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403   -0.1492    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967   -2.3176    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -1.8528    1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    0.6106    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    0.9499    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    2.3036    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2857    0.7198    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    2.7465   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -0.1652   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428   -1.4086    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897   -0.6671   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.3308   -2.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -1.1934    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -3.4911   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8990   -1.8560   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5311   -2.7747    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    0.1529   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491    0.9181    0.6105 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
 10 11  1  0
 10 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  8  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  5 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  1
 10 32  1  1
 11 33  1  0
 12 34  1  1
 13 35  1  0
 14 36  1  6
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  1
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END


  Mrv1652303182019232D          

 23 24  0  0  0  0            999 V2000
 9998.8937 9998.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6084 9999.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.037110000.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4700 9999.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0371 9996.7641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4700 9997.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.463410001.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.748310001.7190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4634 9998.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0330 9998.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.033010000.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.463410000.4796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.749010000.0671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.7490 9999.2421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4634 9998.8297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.1778 9999.2421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.177810000.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0385 9999.2414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3241 9998.8289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3241 9998.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0385 9997.5915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7530 9998.0039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7530 9998.8289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 17  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16  1  1  6  0  0  0
 12  7  1  1  0  0  0
 13 11  1  1  0  0  0
 14 10  1  1  0  0  0
 15  9  1  6  0  0  0
 19  2  1  6  0  0  0
 18  3  1  1  0  0  0
 23  4  1  6  0  0  0
 22  6  1  1  0  0  0
 21  5  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000538

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
DLRVVLDZNNYCBX-CQHUIXDMSA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.2965

> <EXACT_MASS>
342.116211546

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.18665169443941

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.00

> <JCHEM_LOGP>
-4.703374863666666

> <ALOGPS_LOGS>
0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.133081366054801

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.248198780146973

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.3367

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.11e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000048
     RDKit          3D
Melibiose
 45 46  0  0  0  0  0  0  0  0999 V2000
   -3.3490    2.7694   -0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    1.9634   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    0.6490   -1.2039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3499   -0.1776   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -0.8286    0.0708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1367   -1.7354   -0.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099   -1.5788    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -0.2246    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6257   -0.2581    1.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    0.8990    1.5341 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5229    1.9794    1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2149    0.8833    0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9869    2.0993   -0.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -0.2023   -0.6435 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8497   -1.4181   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386    0.0165   -0.7009 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8830    1.3268   -1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3989   -1.6333    0.4697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0815   -2.9622    0.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -1.5135   -0.6582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5481   -2.2614   -0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240   -0.0163   -0.7489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0203    0.3850    0.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117    2.7768   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763    1.7751    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    2.5033   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    0.9274   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403   -0.1492    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967   -2.3176    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -1.8528    1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    0.6106    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    0.9499    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    2.3036    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2857    0.7198    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    2.7465   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -0.1652   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428   -1.4086    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897   -0.6671   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.3308   -2.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -1.1934    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -3.4911   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8990   -1.8560   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5311   -2.7747    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    0.1529   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491    0.9181    0.6105 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
 10 11  1  0
 10 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  8  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  5 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  1
 10 32  1  1
 11 33  1  0
 12 34  1  1
 13 35  1  0
 14 36  1  6
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  1
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  O   UNK     0    8664.6028664.482   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.9368665.251   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.6038666.792   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.2778665.251   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8668.6038660.626   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8671.2778662.168   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.9328669.105   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8660.5978669.875   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8661.9328662.940   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8659.2628664.482   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8659.2628667.563   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8661.9328667.562   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.5988666.792   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.5988665.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.9328664.482   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.2658665.252   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8663.2658666.792   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8668.6058665.251   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.2728664.481   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8667.2728662.941   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8668.6058662.171   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.9398662.941   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8669.9398664.481   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1   19                                                       
CONECT    3   18                                                            
CONECT    4   23                                                            
CONECT    5   21                                                            
CONECT    6   22                                                            
CONECT    7    8   12                                                       
CONECT    8    7                                                            
CONECT    9   15                                                            
CONECT   10   14                                                            
CONECT   11   13                                                            
CONECT   12   13   17    7                                                  
CONECT   13   12   14   11                                                  
CONECT   14   13   15   10                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17    1                                                  
CONECT   17   12   16                                                       
CONECT   18   19   23    3                                                  
CONECT   19   18   20    2                                                  
CONECT   20   19   21                                                       
CONECT   21   22   20    5                                                  
CONECT   22   21   23    6                                                  
CONECT   23   18   22    4                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0000048
HETATM    1  O1  UNL     1      -3.349   2.769  -0.555  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.216   1.963  -0.458  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.431   0.649  -1.204  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.350  -0.178  -1.139  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.179  -0.829   0.071  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.137  -1.735  -0.094  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.910  -1.579   0.776  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.588  -0.225   0.680  1.00  0.00           C  
HETATM    9  O4  UNL     1       2.626  -0.258   1.640  1.00  0.00           O  
HETATM   10  C6  UNL     1       3.395   0.899   1.534  1.00  0.00           C  
HETATM   11  O5  UNL     1       2.523   1.979   1.564  1.00  0.00           O  
HETATM   12  C7  UNL     1       4.215   0.883   0.249  1.00  0.00           C  
HETATM   13  O6  UNL     1       3.987   2.099  -0.400  1.00  0.00           O  
HETATM   14  C8  UNL     1       3.641  -0.202  -0.644  1.00  0.00           C  
HETATM   15  O7  UNL     1       3.850  -1.418  -0.009  1.00  0.00           O  
HETATM   16  C9  UNL     1       2.139   0.016  -0.701  1.00  0.00           C  
HETATM   17  O8  UNL     1       1.883   1.327  -1.130  1.00  0.00           O  
HETATM   18  C10 UNL     1      -2.399  -1.633   0.470  1.00  0.00           C  
HETATM   19  O9  UNL     1      -2.082  -2.962   0.737  1.00  0.00           O  
HETATM   20  C11 UNL     1      -3.402  -1.513  -0.658  1.00  0.00           C  
HETATM   21  O10 UNL     1      -4.548  -2.261  -0.437  1.00  0.00           O  
HETATM   22  C12 UNL     1      -3.724  -0.016  -0.749  1.00  0.00           C  
HETATM   23  O11 UNL     1      -4.020   0.385   0.564  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.612   2.777  -1.526  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.976   1.775   0.618  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.389   2.503  -0.919  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.594   0.927  -2.267  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.940  -0.149   0.901  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.697  -2.318   0.442  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.685  -1.853   1.816  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.936   0.611   1.005  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.037   0.950   2.436  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.387   2.304   2.495  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.286   0.720   0.479  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.734   2.746  -0.214  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.090  -0.165  -1.661  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.643  -1.409   0.590  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.690  -0.667  -1.464  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.062   1.331  -2.109  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.881  -1.193   1.367  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.935  -3.491  -0.093  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.899  -1.856  -1.589  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.531  -2.775   0.407  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.558   0.153  -1.430  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.849   0.918   0.610  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   29   30
CONECT    8    9   16   31
CONECT    9   10
CONECT   10   11   12   32
CONECT   11   33
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

HMDB0000048
     RDKit          3D
Melibiose
 45 46  0  0  0  0  0  0  0  0999 V2000
   -3.3490    2.7694   -0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    1.9634   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    0.6490   -1.2039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3499   -0.1776   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -0.8286    0.0708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1367   -1.7354   -0.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099   -1.5788    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -0.2246    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6257   -0.2581    1.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    0.8990    1.5341 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5229    1.9794    1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2149    0.8833    0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9869    2.0993   -0.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -0.2023   -0.6435 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8497   -1.4181   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386    0.0165   -0.7009 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8830    1.3268   -1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3989   -1.6333    0.4697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0815   -2.9622    0.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -1.5135   -0.6582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5481   -2.2614   -0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240   -0.0163   -0.7489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0203    0.3850    0.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117    2.7768   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763    1.7751    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    2.5033   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    0.9274   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403   -0.1492    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967   -2.3176    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -1.8528    1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    0.6106    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    0.9499    2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    2.3036    2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2857    0.7198    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    2.7465   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -0.1652   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428   -1.4086    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897   -0.6671   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.3308   -2.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -1.1934    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -3.4911   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8990   -1.8560   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5311   -2.7747    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577    0.1529   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491    0.9181    0.6105 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
 10 11  1  0
 10 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  8  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  5 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  1
 10 32  1  1
 11 33  1  0
 12 34  1  1
 13 35  1  0
 14 36  1  6
 15 37  1  0
 16 38  1  6
 17 39  1  0
 18 40  1  1
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  6
 23 45  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
alpha-D-Galacto-hexopyranosyl-(1->6)-alpha-D-gluco-hexopyranose	ChEBI
WURCS=2.0/2,2,1/[a2122h-1a_1-5][a2112h-1a_1-5]/1-2/a6-b1	ChEBI
a-D-Galacto-hexopyranosyl-(1->6)-a-D-gluco-hexopyranose	Generator
Α-D-galacto-hexopyranosyl-(1->6)-α-D-gluco-hexopyranose	Generator
6-O-alpha-D-Galactopyranosyl-D-glucose	HMDB
6-O-alpha-D-Galactopyranosyl-alpha-D-glucopyranose	HMDB
6-O-Α-D-galactopyranosyl-D-glucose	HMDB
6-O-Α-D-galactopyranosyl-α-D-glucopyranose	HMDB
D-(+)-Melibiose	HMDB
D-Melibiose	HMDB
alpha-D-Melibiose	HMDB
alpha-Melibiose	HMDB
Α-D-melibiose	HMDB
Α-melibiose	HMDB
Melibiose	HMDB
a-D-Galp-(1->6)-a-D-GLCP	Generator
Α-D-galp-(1->6)-α-D-GLCP	Generator

Chemical Formula

C₁₂H₂₂O₁₁

Average Mass

342.2965 Da

Monoisotopic Mass

342.11621 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

585-99-9

SMILES

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

InChI Identifier

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

InChI Key

DLRVVLDZNNYCBX-CQHUIXDMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 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
Arabidopsis thaliana	KNApSAcK Database	22123792
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...
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Larix laricina	LOTUS Database	35616633
Pyrus malus	KNApSAcK Database	22123792
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis vinifera L.	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

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	84 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	511 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.17	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	31.19 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

HMDB0000048

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001142

Chemspider ID

5034823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Melibiose

METLIN ID

Not Available

PubChem Compound

6602503

PDB ID

Not Available

ChEBI ID

151217

Good Scents ID

Not Available

References

General References

Almeida IC, Milani SR, Gorin PA, Travassos LR: Complement-mediated lysis of Trypanosoma cruzi trypomastigotes by human anti-alpha-galactosyl antibodies. J Immunol. 1991 Apr 1;146(7):2394-400. [PubMed:1706399 ]
Sharma A, Ahmed H, Allen HJ: Isolation of a melibiose-binding protein from human spleen. Glycoconj J. 1995 Feb;12(1):17-21. [PubMed:7795409 ]
Steuer MK, Steuer M, Bonkowsky V, Gabius HJ, Hofstadter F: Characterization of sugar receptor expression by neoglycoproteins in oral and oropharyngeal squamous cell carcinomas. Eur Arch Otorhinolaryngol. 1995;252(5):292-7. [PubMed:7576587 ]
Vaughan HA, Loveland BE, Sandrin MS: Gal alpha(1,3)Gal is the major xenoepitope expressed on pig endothelial cells recognized by naturally occurring cytotoxic human antibodies. Transplantation. 1994 Oct 27;58(8):879-82. [PubMed:7524207 ]
Barboza Junior MS, Silva TM, Guerrant RL, Lima AA: Measurement of intestinal permeability using mannitol and lactulose in children with diarrheal diseases. Braz J Med Biol Res. 1999 Dec;32(12):1499-504. [PubMed:10585631 ]
Furukawa K, Ying R, Nakajima T, Matsuki T: Hemagglutinins in fungus extracts and their blood group specificity. Exp Clin Immunogenet. 1995;12(4):223-31. [PubMed:8919354 ]
Gibbons RJ, Qureshi JV: Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Infect Immun. 1979 Dec;26(3):1214-7. [PubMed:528053 ]
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Showing NP-Card for Melibiose (NP0000538)

MOL for NP0000538 (Melibiose)

3D MOL for NP0000538 (Melibiose)

3D SDF for NP0000538 (Melibiose)

3D-SDF for NP0000538 (Melibiose)

PDB for NP0000538 (Melibiose)

3D PDB for NP0000538 (Melibiose)

SMILES for NP0000538 (Melibiose)

INCHI for NP0000538 (Melibiose)

Structure for NP0000538 (Melibiose)

3D Structure for NP0000538 (Melibiose)