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Record Information
Version3.6
Creation Date2006-08-12 20:29:38 UTC
Update Date2016-02-11 01:06:17 UTC
HMDB IDHMDB03418
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Tagatose
DescriptionD-Tagatose, a rare natural hexoketose, is an isomer of d-galactose. D-Tagatose occurs naturally in Sterculia setigera gum, and it is also found in small quantities in various foods such as sterilized and powdered cow's milk, hot cocoa, and a variety of cheeses, yogurts, and other dairy products. It can be synthesized from D-galactose by isomerization under alkaline conditions in the presence of calcium. D-Tagatose have numerous health benefits, including promotion of weight loss, no glycemic effect, anti-plaque, non-cariogenic, anti-halitosis, prebiotic, and anti-biofilm properties, organ transplants, enhancement of flavor, improvement of pregnancy and fetal development, treatment of obesity, and reduction in symptoms associated with type 2 diabetes, hyperglycemia, anemia, and hemophilia. (PMID: 17492284 ).
Structure
Thumb
Synonyms
ValueSource
D-TagatoseChEBI
D-lyxo-2-HexuloseHMDB
D-lyxo-Hex-2-uloseHMDB
D-TagHMDB
lyxo-2-HexuloseHMDB
lyxo-HexuloseHMDB
TagatoseHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
Traditional Nametagatose
CAS Registry Number87-81-0
SMILES
OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO
InChI Identifier
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
InChI KeyInChIKey=BJHIKXHVCXFQLS-PQLUHFTBSA-N
Chemical 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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.202Not 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
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04936
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001109
KNApSAcK IDNot Available
Chemspider ID83142
KEGG Compound IDC00795
BioCyc IDTAGATOSE
BiGG ID36022
Wikipedia LinkTagatose
NuGOwiki LinkHMDB03418
Metagene LinkHMDB03418
METLIN IDNot Available
PubChem Compound92092
PDB IDTAG
ChEBI ID47693
References
Synthesis ReferenceKim, Pil; Yoon, Sang Hyun; Seo, Myung Ji; Oh, Deok Kun; Choi, Jin Hwan. Improvement of tagatose conversion rate by genetic evolution of thermostable galactose isomerase. Biotechnology and Applied Biochemistry (2001), 34(2), 99-102.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Oh DK: Tagatose: properties, applications, and biotechnological processes. Appl Microbiol Biotechnol. 2007 Aug;76(1):1-8. Epub 2007 May 10. [17492284 ]
  2. 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. [11225640 ]