Showing metabocard for D-Xylitol (MMDBc0000222)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:40:19 UTC
Update Date2024-04-30 19:31:33 UTC
Metabolite IDMMDBc0000222
Metabolite Identification
Common NameD-Xylitol
DescriptionXylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by humans. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol can be produced industrially starting from primary matters rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in the corn raids, the almond hulls or the barks of birch (or of the by-products of wood: shavings hard, paper pulp). Of all polyols, it is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to his use in confectionery, it is used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced mutans streptococci levels in saliva and plaque in adults (PMID: 17426399 , 15964535 ). Studies have also shown xylitol chewing gum can help prevent acute otitis media (ear aches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Xylitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9238729fa8>

00508.mol
  Mrv1652303202019292D          

 10  9  0  0  0  0            999 V2000
   -2.1459   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7163   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4297    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1459   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  1  0  0  0
  3  9  1  1  0  0  0
  5 10  1  1  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9238729fa8>

HMDB0002917
     RDKit          3D
D-Xylitol
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.7859    1.7060   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804    0.7945    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364    0.1992   -0.7203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9427   -0.4443   -1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -0.8927   -0.2458 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5342   -1.4484   -1.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892   -0.4271    0.6578 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5435    0.1431    1.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    0.4665   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    0.6503    0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5057    1.2015   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5216    0.0464    0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    1.3372    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.9877   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1956   -1.2862   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951   -1.6592    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -2.3045   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.3421    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -0.0616    2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4401   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095   -0.0314   -0.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.9250    0.2992 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  6
  4 15  1  0
  5 16  1  1
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9238729fa8>

00508.mol
  Mrv1652303202019292D          

 10  9  0  0  0  0            999 V2000
   -2.1459   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7163   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4297    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1459   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  1  0  0  0
  3  9  1  1  0  0  0
  5 10  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000222

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+

> <INCHI_KEY>
HEBKCHPVOIAQTA-SCDXWVJYSA-N

> <FORMULA>
C5H12O5

> <MOLECULAR_WEIGHT>
152.1458

> <EXACT_MASS>
152.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.421768323067532

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3r,4S)-pentane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.53

> <JCHEM_LOGP>
-3.099683906666666

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.742189661908146

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.760078510562963

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742034412471314

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
32.4411

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xylitol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9238729fa8>

HMDB0002917
     RDKit          3D
D-Xylitol
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.7859    1.7060   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804    0.7945    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364    0.1992   -0.7203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9427   -0.4443   -1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -0.8927   -0.2458 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5342   -1.4484   -1.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892   -0.4271    0.6578 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5435    0.1431    1.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    0.4665   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    0.6503    0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5057    1.2015   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5216    0.0464    0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    1.3372    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.9877   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1956   -1.2862   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951   -1.6592    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -2.3045   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.3421    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -0.0616    2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4401   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095   -0.0314   -0.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.9250    0.2992 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  6
  4 15  1  0
  5 16  1  1
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
M  END
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PDB for #<Metabolite:0x00007f9238729fa8>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 00508.mol                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0      -4.006  -0.385   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.669   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.332  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.337  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.669   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.006  -0.385   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   1.925   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.332  -1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.337  -1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    3                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f9238729fa8>

COMPND    HMDB0002917
HETATM    1  O1  UNL     1      -2.786   1.706  -0.233  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.880   0.795   0.363  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.036   0.199  -0.720  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.943  -0.444  -1.601  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.113  -0.893  -0.246  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.534  -1.448  -1.379  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.989  -0.427   0.658  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.543   0.143   1.834  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.985   0.467  -0.064  1.00  0.00           C  
HETATM   10  O5  UNL     1       3.065   0.650   0.818  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.506   1.201  -0.709  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.522   0.046   0.871  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.316   1.337   1.146  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.492   0.988  -1.270  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.196  -1.286  -1.111  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.695  -1.659   0.277  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.929  -2.304  -1.147  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.564  -1.342   0.945  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.136  -0.062   2.602  1.00  0.00           H  
HETATM   20  H10 UNL     1       1.567   1.440  -0.333  1.00  0.00           H  
HETATM   21  H11 UNL     1       2.309  -0.031  -1.000  1.00  0.00           H  
HETATM   22  H12 UNL     1       3.863   0.925   0.299  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3   12   13
CONECT    3    4    5   14
CONECT    4   15
CONECT    5    6    7   16
CONECT    6   17
CONECT    7    8    9   18
CONECT    8   19
CONECT    9   10   20   21
CONECT   10   22
END
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SMILES for #<Metabolite:0x00007f9238729fa8>

OC[C@H](O)[C@@H](O)[C@H](O)CO
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INCHI for #<Metabolite:0x00007f9238729fa8>

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
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Synonyms
ValueSource
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaolChEBI
XylitChEBI
XyliteChEBI
Xylo-pentitolHMDB
XylitolHMDB
D-XYLITOLChEBI
Molecular FormulaC5H12O5
Average Mass152.1458
Monoisotopic Mass152.068473494
IUPAC Name(2R,3r,4S)-pentane-1,2,3,4,5-pentol
Traditional Namexylitol
CAS Registry Number87-99-0
SMILES
OC[C@H](O)[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
InChI KeyHEBKCHPVOIAQTA-SCDXWVJYSA-N