Showing NP-Card for Galactitol (NP0000604)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:40:57 UTC
NP-MRD IDNP0000604
Secondary Accession NumbersNone
Natural Product Identification
Common NameGalactitol
DescriptionGalactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. Galactitol has a slightly sweet taste. It is produced from galactose in a reaction catalyzed by aldose reductase. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individual's ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000604 (Galactitol)

  Mrv1652303202019002D          

 12 11  0  0  1  0            999 V2000
   13.6187   -7.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9043   -9.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3332   -9.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1899   -7.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7620   -8.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7610   -8.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6187   -8.5741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9043   -8.9867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3332   -8.9867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1899   -8.5741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0475   -8.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4755   -8.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  8  2  1  6  0  0  0
  9  3  1  1  0  0  0
 10  4  1  6  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000604 (Galactitol)

HMDB0000107
     RDKit          3D
Galactitol
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.9342    0.3703    0.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    0.8099   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.3824   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8250   -1.3518    0.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361   -0.0203   -0.6970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2501    0.9608   -1.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    0.3464    0.5526 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3255   -0.6494    1.5224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.6531    0.3357 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0961    1.6352   -0.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032   -0.5624    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154   -1.0954   -1.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472   -0.3675   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.2674    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521    1.5543   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1823   -0.8001   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147   -2.2276    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.9422   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    0.5552   -2.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    1.2540    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993   -1.5222    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403    1.0484    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534    2.4243   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.2730    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5168   -1.3235    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -1.3613   -1.6246 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
  9 11  1  0
 11 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  6
  4 17  1  0
  5 18  1  6
  6 19  1  0
  7 20  1  1
  8 21  1  0
  9 22  1  1
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

3D SDF for NP0000604 (Galactitol)

  Mrv1652303202019002D          

 12 11  0  0  1  0            999 V2000
   13.6187   -7.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9043   -9.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3332   -9.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1899   -7.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7620   -8.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7610   -8.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6187   -8.5741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9043   -8.9867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3332   -8.9867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1899   -8.5741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0475   -8.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4755   -8.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  8  2  1  6  0  0  0
  9  3  1  1  0  0  0
 10  4  1  6  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000604

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-

> <INCHI_KEY>
FBPFZTCFMRRESA-GUCUJZIJSA-N

> <FORMULA>
C6H14O6

> <MOLECULAR_WEIGHT>
182.1718

> <EXACT_MASS>
182.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.246117178806152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol

> <ALOGPS_LOGP>
-2.68

> <JCHEM_LOGP>
-3.7300188486666666

> <ALOGPS_LOGS>
0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.37874915684328

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.585200956788803

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974211614825128

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
38.403600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galactitol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000604 (Galactitol)

HMDB0000107
     RDKit          3D
Galactitol
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.9342    0.3703    0.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    0.8099   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.3824   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8250   -1.3518    0.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361   -0.0203   -0.6970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2501    0.9608   -1.6747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    0.3464    0.5526 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3255   -0.6494    1.5224 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    0.6531    0.3357 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0961    1.6352   -0.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032   -0.5624    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154   -1.0954   -1.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472   -0.3675   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.2674    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521    1.5543   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1823   -0.8001   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147   -2.2276    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.9422   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    0.5552   -2.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    1.2540    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993   -1.5222    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403    1.0484    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534    2.4243   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.2730    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5168   -1.3235    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -1.3613   -1.6246 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
  9 11  1  0
 11 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  6
  4 17  1  0
  5 18  1  6
  6 19  1  0
  7 20  1  1
  8 21  1  0
  9 22  1  1
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

PDB for NP0000604 (Galactitol)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0      25.422 -14.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      24.088 -18.315   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.755 -18.315   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.754 -14.465   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      29.422 -16.775   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      20.087 -16.005   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.422 -16.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.088 -16.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.755 -16.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.754 -16.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.089 -16.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.421 -16.775   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   11                                                            
CONECT    6   12                                                            
CONECT    7    1    8    9                                                  
CONECT    8    2    7   10                                                  
CONECT    9    3    7   11                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5    9                                                       
CONECT   12    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000604 (Galactitol)

COMPND    HMDB0000107
HETATM    1  O1  UNL     1      -3.934   0.370   0.074  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.619   0.810  -0.066  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.778  -0.382  -0.413  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.825  -1.352   0.555  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.336  -0.020  -0.697  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.250   0.961  -1.675  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.411   0.346   0.553  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.326  -0.649   1.522  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.869   0.653   0.336  1.00  0.00           C  
HETATM   10  O5  UNL     1       2.096   1.635  -0.627  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.703  -0.562   0.061  1.00  0.00           C  
HETATM   12  O6  UNL     1       2.415  -1.095  -1.186  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.147  -0.367  -0.563  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.299   1.267   0.901  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.552   1.554  -0.892  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.182  -0.800  -1.372  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.715  -2.228   0.135  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.117  -0.942  -1.110  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.107   0.555  -2.572  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.052   1.254   1.050  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.499  -1.522   1.092  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.240   1.048   1.338  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.553   2.424  -0.370  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.772  -0.273   0.160  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.517  -1.324   0.857  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.278  -1.361  -1.625  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4    5   16
CONECT    4   17
CONECT    5    6    7   18
CONECT    6   19
CONECT    7    8    9   20
CONECT    8   21
CONECT    9   10   11   22
CONECT   10   23
CONECT   11   12   24   25
CONECT   12   26
END
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SMILES for NP0000604 (Galactitol)

OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
Download

INCHI for NP0000604 (Galactitol)

InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
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View in JSmol
Synonyms
ValueSource
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
D-DulcitolChEBI
D-GalactitolChEBI
DulcitolChEBI
DulcoseChEBI
EuonymitChEBI
L-GalactitolChEBI
MelampyrinChEBI
MelampyritChEBI
Ambap5938HMDB
DulciteHMDB
HexitolHMDB
MelampyriteHMDB
MelampyrumHMDB
Meso-galactitolHMDB
Chemical FormulaC6H14O6
Average Mass182.1718 Da
Monoisotopic Mass182.07904 Da
IUPAC Name(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional Namegalactitol
CAS Registry Number608-66-2
SMILES
OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
InChI KeyFBPFZTCFMRRESA-GUCUJZIJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-02View Spectrum
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mL at 15 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP-3.10Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000107
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030767
KNApSAcK IDC00001160
Chemspider ID11357
KEGG Compound IDC01697
BioCyc IDNot Available
BiGG ID38183
Wikipedia LinkGalactitol
METLIN ID5148
PubChem Compound11850
PDB IDNot Available
ChEBI ID16813
Good Scents IDrw1306661
References
General References