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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:29:38 UTC
Update Date2021-09-14 15:44:47 UTC
HMDB IDHMDB0003418
Secondary Accession Numbers
  • HMDB03418
Metabolite Identification
Common NameD-Tagatose
DescriptionD-Tagatose (CAS: 87-81-0), 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 has 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; obesity treatment; and reduction in symptoms associated with type 2 diabetes, hyperglycemia, anemia, and hemophilia (PMID:17492284 ).
Structure
Data?1582752276
Synonyms
ValueSource
D-Lyxo-2-hexuloseHMDB
D-Lyxo-hex-2-uloseHMDB
D-TagHMDB
Lyxo-2-hexuloseHMDB
Lyxo-hexuloseHMDB
TagatoseHMDB
Tagatose, (D)-isomerHMDB
Tagatose, (beta-D)-isomerHMDB
Tagatose, (alpha-D)-isomerHMDB
Tagatose, (DL)-isomerHMDB
D-TagatopyranoseHMDB
TagatopyranoseHMDB
beta-D-TagatopyranoseHMDB
beta-D-TagatoseHMDB
Β-D-tagatopyranoseHMDB
Β-D-tagatoseHMDB
b-D-TagatopyranoseHMDB
D-TagatoseHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.156
Monoisotopic Molecular Weight180.063388106
IUPAC Name(2R,3S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameβ-D-tagatopyranose
CAS Registry Number20197-42-6
SMILES
OC[C@@]1(O)OC[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5+,6-/m1/s1
InChI KeyLKDRXBCSQODPBY-DPYQTVNSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.202Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility399 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg129.77230932474
AllCCS[M-H]-ExperimentalNot Available129.772http://allccs.zhulab.cn/database/detail?ID=AllCCS00000396

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
D-Tagatose,1TMS,#11752.9675https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#21742.4346https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#31751.6187https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#41737.4463https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#51753.5137https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#11727.3402https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#21731.9012https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#31737.4377https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#41727.8997https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#51744.1982https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#61734.4967https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#71733.7573https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#81723.2323https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#91688.9996https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#101704.1431https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#11750.2974https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#21767.7611https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#31738.1187https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#41713.7587https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#51747.4048https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#61743.852https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#71741.2212https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#81733.3438https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#91754.151https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#101698.2463https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#11780.2516https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#21788.9886https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#31828.2352https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#41767.6804https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#51784.7595https://arxiv.org/abs/1905.12712
D-Tagatose,5TMS,#11903.7284https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#12006.5377https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#22009.8174https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#31988.6361https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#41962.1846https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#51973.6067https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#12193.4688https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#22199.503https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#32185.5747https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#42185.439https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#52204.7117https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#62186.0137https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#72181.9297https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#82176.063https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#92151.4893https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#102159.538https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#12432.5461https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#22427.159https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#32413.2021https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#42419.6245https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#52436.7866https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#62430.6118https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#72421.9028https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#82431.1104https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#92428.2686https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#102409.5088https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#12666.833https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#22650.9458https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#32647.7903https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#42658.429https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#52658.8936https://arxiv.org/abs/1905.12712
D-Tagatose,5TBDMS,#12868.984https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxs-0931000000-9deccc61a68dc8c51aa72019-05-23View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0930000000-e1672ba6560efb925aa52019-05-23View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0931000000-9deccc61a68dc8c51aa72019-05-23View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-e1672ba6560efb925aa52019-05-23View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-c785d191926ead60dc632019-05-23View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0930000000-0c79b52b64467170ea342019-05-23View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-1900000000-72ad7431e281814fc59a2019-05-23View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kb-9000000000-ac1464fac3ca774eb08b2019-05-23View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mk-9000000000-4bc4673c212944cded872019-05-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6900000000-def874fe6470032fdd272021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9100000000-b495c0f16251b5ee98e12021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-d526231c78d5ea2b9be52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pk-0900000000-d9de28ed437f1079125e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9700000000-21b6c695fb9bdd5ae08d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-7c49e3a2d60cfed68a762021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2019-05-23View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, H2O, predicted)2019-05-23View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001109
KNApSAcK IDNot Available
Chemspider ID10194220
KEGG Compound IDC00795
BioCyc IDD-tagatose
BiGG IDNot Available
Wikipedia LinkTagatose
METLIN IDNot Available
PubChem Compound14408225
PDB IDNot Available
ChEBI ID49092
Food Biomarker OntologyNot Available
VMH IDTAGAT_D
MarkerDB IDNot Available
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 ]