MiMeDB: Showing metabocard for Galactitol (MMDBc0000027)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:27:42 UTC

Update Date

2024-04-30 19:30:53 UTC

Metabolite ID

MMDBc0000027

Metabolite Identification

Common Name

Galactitol

Description

Galactitol 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

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

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

Synonyms

Value	Source
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexol	ChEBI
D-Dulcitol	ChEBI
D-Galactitol	ChEBI
Dulcitol	ChEBI
Dulcose	ChEBI
Euonymit	ChEBI
L-Galactitol	ChEBI
Melampyrin	ChEBI
Melampyrit	ChEBI
Ambap5938	HMDB
Dulcite	HMDB
Hexitol	HMDB
Melampyrite	HMDB
Melampyrum	HMDB
meso-Galactitol	HMDB

Molecular Formula

C₆H₁₄O₆

Average Mass

182.1718

Monoisotopic Mass

182.07903818

IUPAC Name

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

Traditional Name

galactitol

CAS Registry Number

608-66-2

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 Key

FBPFZTCFMRRESA-GUCUJZIJSA-N

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hexitol (CHEBI:16813 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	229 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.7	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.4 m³·mol⁻¹	ChemAxon
Polarizability	17.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Amniotic Fluid
Blood
Brain
Cerebrospinal Fluid (CSF)
Erythrocyte
Eye Lens
Feces
Saliva
Urine

Tissue Locations

Brain
Erythrocyte
Eye Lens

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191761	Aldose reductase	Unknown	P15121	Homo sapiens
MMDBp0196682	Aldo-keto reductase family 1 member B10	Unknown	O60218

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025317	Galactitol	L-Histidine	PTS system galactitol-specific EIIB component	Phosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	8595727
Galactosemia		Association	Human Amniotic Fluid	HMDB	6433315
Galactosemia	Increased	Association	Human Blood	HMDB	11092512
Galactosemia	Increased	Association	Human Urine	HMDB	7671965

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	58	Human saliva; Human feces; Human stool; Human urine; Human appendix biopsy; Human ; Human gastric fluid	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	291	Human feces; Human urine; Human ; Pig ; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human stool; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	78	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	132	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	9	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Firmicutes	20	Human feces; Human urine; Human ; Pig ; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human stool; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	11	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	5	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.65	0.22			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	8595727
Human Amniotic fluid	Detected and Quantified	7.96				uM	Adult (>18 years old)	Both	Galactosemia	HMDB	6433315
Human Blood	Detected and Quantified	11.63	0.46			uM	Adult (>18 years old)	Both	Galactosemia	HMDB	11092512
Human Urine	Detected and Quantified	38500		8000	69000	umol/mmol creatinine	Adult (>18 years old)	Both	Galactosemia	HMDB	7671965
Human Urine	Detected and Quantified	472.5		45	900	umol/mmol creatinine	Adult (>18 years old)	Both	Galactosemia	HMDB	7671965
Human Urine	Detected and Quantified			0	30	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Blood	Detected and Quantified	0.36		0.23	0.48	uM	Adult (>18 years old)	Both	Normal	HMDB	7710082
Human Amniotic fluid	Detected and Quantified	0.7	0.18			uM	Not Specified	Both	Normal	HMDB	6433315
Human Blood	Detected and Quantified	0.82		0.05	2.63	uM	Adult (>18 years old)	Both	Normal	HMDB	6434200
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.65	0.44			uM	Adult (>18 years old)	Both	Normal	HMDB	8595727
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.82		1.17	2.47	uM	Adult (>18 years old)	Both	Normal	HMDB	7710082
Human Urine	Detected and Quantified	42		3	81	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7671965
Human Urine	Detected and Quantified	3.7		0.0	12.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	19.44	4.95			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Eye lens	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21330412

External Links

HMDB ID

HMDB0000107

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16813

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ning C, Segal S: Plasma galactose and galactitol concentration in patients with galactose-1-phosphate uridyltransferase deficiency galactosemia: determination by gas chromatography/mass spectrometry. Metabolism. 2000 Nov;49(11):1460-6. doi: 10.1053/meta.2000.9512. [PubMed:11092512 ]
Jakobs C, Warner TG, Sweetman L, Nyhan WL: Stable isotope dilution analysis of galactitol in amniotic fluid: an accurate approach to the prenatal diagnosis of galactosemia. Pediatr Res. 1984 Aug;18(8):714-8. doi: 10.1203/00006450-198408000-00007. [PubMed:6433315 ]
Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. doi: 10.1203/00006450-200008000-00015. [PubMed:10926297 ]
Budde M, Gusek-Schneider GC, Junemann A, Jansen F, Shin YS: [Familial cataract in plasma galactitol increase without known enzyme defect]. Klin Monbl Augenheilkd. 1999 Oct;215(4):255-7. doi: 10.1055/s-2008-1034710. [PubMed:10572890 ]
Berry GT, Hunter JV, Wang Z, Dreha S, Mazur A, Brooks DG, Ning C, Zimmerman RA, Segal S: In vivo evidence of brain galactitol accumulation in an infant with galactosemia and encephalopathy. J Pediatr. 2001 Feb;138(2):260-2. doi: 10.1067/mpd.2001.110423. [PubMed:11174626 ]
Pettit BR, King GS, Blau K: The analysis of hexitols in biological fluid by selected ion monitoring. Biomed Mass Spectrom. 1980 Jul;7(7):309-13. doi: 10.1002/bms.1200070708. [PubMed:7448335 ]
Ficicioglu C, Yager C, Segal S: Galactitol and galactonate in red blood cells of children with the Duarte/galactosemia genotype. Mol Genet Metab. 2005 Feb;84(2):152-9. doi: 10.1016/j.ymgme.2004.11.001. Epub 2004 Dec 9. [PubMed:15670721 ]
Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. doi: 10.1007/BF02143804. [PubMed:7671965 ]
Roboz J, Kappatos DC, Greaves J, Holland JF: Determination of polyols in serum by selected ion monitoring. Clin Chem. 1984 Oct;30(10):1611-5. [PubMed:6434200 ]
Airey CM, Price DE, Kemp JV, Perkins CM, Wales JK: The effect of aldose reductase inhibition on erythrocyte polyols and galactitol accumulation in diabetic patients. Diabet Med. 1989 Dec;6(9):804-8. doi: 10.1111/j.1464-5491.1989.tb01283.x. [PubMed:2533041 ]
Schwarz HP, Schaefer T, Bachmann C: Galactose and galactitol in the urine of children with compound heterozygosity for Duarte variant and classical galactosemia (GtD/gt) after an oral galactose load. Clin Chem. 1985 Mar;31(3):420-2. [PubMed:3971562 ]
Arola H, Sillanaukee P, Aine E, Koivula T, Isokoski M: Galactitol is not a cause of senile cataract. Graefes Arch Clin Exp Ophthalmol. 1992;230(3):240-2. doi: 10.1007/BF00176297. [PubMed:1597290 ]
Allen JT, Holton JB, Gillett MG: Gas-liquid chromatographic determination of galactitol in amniotic fluid for possible use in prenatal diagnosis of galactosaemia. Clin Chim Acta. 1981 Feb 19;110(1):59-63. doi: 10.1016/0009-8981(81)90300-4. [PubMed:7214715 ]
Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. doi: 10.1006/abio.1995.1041. [PubMed:7710082 ]
Berry GT, Palmieri M, Gross KC, Acosta PB, Henstenburg JA, Mazur A, Reynolds R, Segal S: The effect of dietary fruits and vegetables on urinary galactitol excretion in galactose-1-phosphate uridyltransferase deficiency. J Inherit Metab Dis. 1993;16(1):91-100. doi: 10.1007/BF00711320. [PubMed:8487507 ]

Showing metabocard for Galactitol (MMDBc0000027)

MOL for #<Metabolite:0x00007f91ed4b5470>

3D MOL for #<Metabolite:0x00007f91ed4b5470>

3D SDF for #<Metabolite:0x00007f91ed4b5470>

3D-SDF for #<Metabolite:0x00007f91ed4b5470>

PDB for #<Metabolite:0x00007f91ed4b5470>

3D PDB for #<Metabolite:0x00007f91ed4b5470>

SMILES for #<Metabolite:0x00007f91ed4b5470>

INCHI for #<Metabolite:0x00007f91ed4b5470>

Structure for #<Metabolite:0x00007f91ed4b5470>

3D Structure for #<Metabolite:0x00007f91ed4b5470>