Tagatose

Identification

Name
Tagatose
Accession Number
DB04936
Type
Small Molecule
Groups
Investigational
Description

Tagatose is a functional sweetener. It is a naturally occurring monosaccharide, specifically a hexose. It is often found in dairy products, and is very similar in texture to sucrose (table sugar) and is 92% as sweet, but with only 38% of the calories. It is approved as a food additive as a low calorie sweetener. Additionally, it is under investigation by Spherix for the treatment of obesity and type II diabetes.

Structure
Thumb
Synonyms
  • D-lyxo-hex-2-ulose
  • D-lyxo-hexulose
  • D-tag
  • D-tagatose
International/Other Brands
Naturlose
Categories
UNII
T7A20Y888Y
CAS number
87-81-0
Weight
Average: 180.1559
Monoisotopic: 180.063388116
Chemical Formula
C6H12O6
InChI Key
BJHIKXHVCXFQLS-PQLUHFTBSA-N
InChI
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6-/m1/s1
IUPAC Name
(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
SMILES
OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO

Pharmacology

Indication

Intended for use as a therapeutic adjunct in the treatment of type II diabetes.

Pharmacodynamics

Oral tagatose significantly blunts the rise in plasma glucose seen after oral glucose in patients with diabetes mellitus in a dose-dependent manner without significantly affecting insulin levels. The minimal elevation of plasma tagatose levels in normal patients and the adverse gastrointestinal effects seen following larger doses of tagatose support poor absorption of this hexose and suggest that tagatose may act by attenuating glucose absorption in the intestine.

Mechanism of action

he steps in the metabolism of tagatose are identical to those for fructose or fruit sugar but tagatose is incompletely absorbed. Only 15-20 percent of tagatose is absorbed in the small intestine. The major part of ingested tagatose is fermented in the colon by indigenous microflora, resulting in the production of short-chain fatty acids. The short chain fatty acids are absorbed almost completely and metabolized.

Absorption

Only 15-20 percent of tagatose is absorbed in the small intestine.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Since it is metabolized differently from sucrose, tagatose has a minimal effect on blood glucose and insulin levels.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Technetium Tc-99m oxidronateTagatose can cause a decrease in the absorption of Technetium Tc-99m oxidronate resulting in a reduced serum concentration and potentially a decrease in efficacy.
Food Interactions
Not Available

References

General References
  1. Donner TW, Wilber JF, Ostrowski D: D-tagatose, a novel hexose: acute effects on carbohydrate tolerance in subjects with and without type 2 diabetes. Diabetes Obes Metab. 1999 Sep;1(5):285-91. [PubMed:11225640]
External Links
Human Metabolome Database
HMDB0003418
PubChem Compound
92092
PubChem Substance
175426910
ChemSpider
83142
ChEBI
47693
HET
TAG
Wikipedia
Tagatose
PDB Entries
2qum / 3vnl
MSDS
Download (69.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)133-135 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility399.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-3.3ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.56 m3·mol-1ChemAxon
Polarizability16.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7519
Blood Brain Barrier-0.5821
Caco-2 permeable-0.8899
P-glycoprotein substrateNon-substrate0.6377
P-glycoprotein inhibitor INon-inhibitor0.9527
P-glycoprotein inhibitor IINon-inhibitor0.9369
Renal organic cation transporterNon-inhibitor0.9292
CYP450 2C9 substrateNon-substrate0.8653
CYP450 2D6 substrateNon-substrate0.8805
CYP450 3A4 substrateNon-substrate0.7379
CYP450 1A2 substrateNon-inhibitor0.8273
CYP450 2C9 inhibitorNon-inhibitor0.9441
CYP450 2D6 inhibitorNon-inhibitor0.9417
CYP450 2C19 inhibitorNon-inhibitor0.9346
CYP450 3A4 inhibitorNon-inhibitor0.9195
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9652
Ames testNon AMES toxic0.8597
CarcinogenicityNon-carcinogens0.7946
BiodegradationReady biodegradable0.913
Rat acute toxicity1.4430 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9837
hERG inhibition (predictor II)Non-inhibitor0.9306
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0uxs-0931000000-9deccc61a68dc8c51aa7
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0uxr-0930000000-e1672ba6560efb925aa5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uxs-0931000000-9deccc61a68dc8c51aa7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uxr-0930000000-e1672ba6560efb925aa5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0920000000-c785d191926ead60dc63
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uxs-0930000000-0c79b52b64467170ea34
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-001i-1900000000-72ad7431e281814fc59a
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00kb-9000000000-ac1464fac3ca774eb08b
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-05mk-9000000000-4bc4673c212944cded87
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Monosaccharides
Alternative Parents
Beta-hydroxy ketones / Acyloins / Alpha-hydroxy ketones / Secondary alcohols / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Monosaccharide / Beta-hydroxy ketone / Acyloin / Alpha-hydroxy ketone / Secondary alcohol / Ketone / Polyol / Organic oxide / Hydrocarbon derivative / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tagatose, D-tagatose (CHEBI:47693)

Drug created on October 21, 2007 16:23 / Updated on October 01, 2018 13:58