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Record Information
Version4.0
Creation Date2006-08-12 20:29:38 UTC
Update Date2017-09-27 08:24:21 UTC
HMDB IDHMDB0003418
Secondary Accession Numbers
  • HMDB03418
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-lyxo-2-HexuloseHMDB
D-lyxo-Hex-2-uloseHMDB
D-TagHMDB
lyxo-2-HexuloseHMDB
lyxo-HexuloseHMDB
TagatoseHMDB
Tagatose, (D)-isomerMeSH
Tagatose, (beta-D)-isomerMeSH
Tagatose, (alpha-D)-isomerMeSH
Tagatose, (DL)-isomerMeSH
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 KeyBJHIKXHVCXFQLS-PQLUHFTBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.56 m³·mol⁻¹ChemAxon
Polarizability16.44 ųChemAxon
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) (Non-derivatized)splash10-0uxs-0931000000-9deccc61a68dc8c51aa7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0930000000-e1672ba6560efb925aa5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0931000000-9deccc61a68dc8c51aa7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-e1672ba6560efb925aa5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-c785d191926ead60dc63View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0930000000-0c79b52b64467170ea34View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9400000000-cbf0535ab90e3a601a7aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-5303980000-07ca5d770983bd06de30View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-87bee64df7fe316d7affView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-eb4eeb92523e2e200555View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-9100000000-3f790be8b14df714880bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0170-7900000000-041fe274da364a106e71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9300000000-6f545044f1769c501e2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b0a05227494224e23bd2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>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
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. [PubMed: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. [PubMed:11225640 ]