Showing Compound Card for Galactitol (CDB006163)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:11 UTC
Updated at2020-12-07 19:06:57 UTC
CannabisDB IDCDB006163
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGalactitol
DescriptionGalactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactitol is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. It is this galactose that is broken down to galactitol via a reaction catalyzed by aldose reductase. Galactitol has a slightly sweet taste. 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. Outside of the human body, Galactitol has been detected, but not quantified in, several different foods, such as common buckwheats, winter squash, calabash, black walnuts, and peanuts. This could make galactitol a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Molecular Weight182.17
Monoisotopic Molecular Weight182.079
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling Point275-280 °CWikipedia
Water Solubility31 mg/mL at 15 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGalactitol, non-derivatized, GC-MS Spectrumsplash10-014j-0941000000-61141f9f2ddc66e0b016Spectrum
GC-MSGalactitol, 6 TMS, GC-MS Spectrumsplash10-0gb9-1983000000-0a0dafcfea843fbb3c72Spectrum
GC-MSGalactitol, non-derivatized, GC-MS Spectrumsplash10-014j-0941000000-61141f9f2ddc66e0b016Spectrum
GC-MSGalactitol, non-derivatized, GC-MS Spectrumsplash10-0gb9-1983000000-0a0dafcfea843fbb3c72Spectrum
Predicted GC-MSGalactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-9400000000-7a0f08ea65cbca1920f5Spectrum
Predicted GC-MSGalactitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4Spectrum
Predicted GC-MSGalactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGalactitol, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-005a-5900000000-35da0de23de5b9170aed2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-552b84764ceb9b497a7e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-052f-9000000000-dfb4eef021d94d5145882012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, negativesplash10-001i-0900000000-028ff289dc870279e2182020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-001i-1900000000-a99ee988b2a1bbab91372020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-0uyr-6900000000-04315425478b660c89472020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-0kg9-9400000000-54350b0516f39f8c9b502020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-0abi-9100000000-b4cf2b00830b765d5dcb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0089-9000000000-20463a683f8ab7aa9e4d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0udi-0900000000-43b7e571c1185de1e99b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-00di-9000000000-160eaf7ef39d088537382020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0udi-3900000000-3114e2bfe0cdbc68be192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000j-9000000000-635a869063bea88c00912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0uk9-3900000000-2ecc694b3a9844ec3ee52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-03di-0900000000-61d17fd37e0e3ac16e372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-03di-1900000000-90b308bca6baee5ab0182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0ik9-2900000000-eb87481835668a3b0d3d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0w29-5900000000-a78bc11bf7d88c2b913e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0udi-8900000000-0ae9e05f3f4517635bba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0zmi-9500000000-4156ee30d358f68b25902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0udi-3900000000-0370fdfaee1df82b525d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-05fr-9000000000-9699f16da2c5fbaef32d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000j-9000000000-0a119385f247c8ed7ae42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-014i-0490000000-403aabe62ebe0fa60ab32020-07-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldose reductaseAKR1B17q35P15121 details
Aldo-keto reductase family 1 member B10AKR1B10O60218 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000107
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006453
KNApSAcK IDC00001160
Chemspider ID11357
KEGG Compound IDC01697
BioCyc IDNot Available
BiGG ID38183
Wikipedia LinkGalactitol
METLIN ID5148
PubChem Compound11850
PDB IDNot Available
ChEBI ID16813
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldose reductase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Enzyme Details
2. Aldo-keto reductase family 1 member B10
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available