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Identification
NameTagatose
Accession NumberDB04936
TypeSmall Molecule
GroupsInvestigational
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NaturloseNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIT7A20Y888Y
CAS number87-81-0
WeightAverage: 180.1559
Monoisotopic: 180.063388116
Chemical FormulaC6H12O6
InChI KeyInChIKey=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)[[email protected]](O)[[email protected]](O)C(=O)CO
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationIntended for use as a therapeutic adjunct in the treatment of type II diabetes.
PharmacodynamicsOral 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 actionhe 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.
Related Articles
AbsorptionOnly 15-20 percent of tagatose is absorbed in the small intestine.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point133-135 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0uxs-0931000000-9deccc61a68dc8c51aa7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0uxr-0930000000-e1672ba6560efb925aa5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-1900000000-72ad7431e281814fc59aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kb-9000000000-ac1464fac3ca774eb08bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mk-9000000000-4bc4673c212944cded87View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (69.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on October 21, 2007 16:23 / Updated on August 17, 2016 12:24