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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-12 20:29:38 UTC

Update Date

2021-09-14 15:44:47 UTC

HMDB ID

HMDB0003418

Secondary Accession Numbers

HMDB03418

Metabolite Identification

Common Name

D-Tagatose

Description

D-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

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      28.955 -12.604   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.554 -13.696   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.061 -13.007   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.415 -11.449   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.727 -12.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.393 -13.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.393 -14.547   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.060 -15.317   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.727 -15.317   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.727 -16.857   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      26.061 -14.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      27.394 -15.317   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    3    9   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/OC%5BC@@%5D1(O)OC%5BC@@H%5D(O)%... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       3.126  -0.832  -0.029  1.00  0.00           O  
HETATM    2  C   UNL     1       2.188  -0.062   0.725  1.00  0.00           C  
HETATM    3  C   UNL     1       0.845  -0.034  -0.008  1.00  0.00           C  
HETATM    4  O   UNL     1       1.018   0.556  -1.298  1.00  0.00           O  
HETATM    5  O   UNL     1       0.356  -1.368  -0.156  1.00  0.00           O  
HETATM    6  C   UNL     1      -0.888  -1.459  -0.854  1.00  0.00           C  
HETATM    7  C   UNL     1      -1.963  -0.692  -0.080  1.00  0.00           C  
HETATM    8  H   UNL     1      -2.902  -0.723  -0.633  1.00  0.00           H  
HETATM    9  O   UNL     1      -2.146  -1.291   1.205  1.00  0.00           O  
HETATM   10  C   UNL     1      -1.518   0.763   0.091  1.00  0.00           C  
HETATM   11  H   UNL     1      -2.253   1.302   0.690  1.00  0.00           H  
HETATM   12  O   UNL     1      -1.401   1.381  -1.192  1.00  0.00           O  
HETATM   13  C   UNL     1      -0.160   0.791   0.800  1.00  0.00           C  
HETATM   14  H   UNL     1      -0.262   0.364   1.798  1.00  0.00           H  
HETATM   15  O   UNL     1       0.299   2.140   0.901  1.00  0.00           O  
HETATM   16  H   UNL     1       4.002  -0.893   0.377  1.00  0.00           H  
HETATM   17  H   UNL     1       2.056  -0.512   1.709  1.00  0.00           H  
HETATM   18  H   UNL     1       2.561   0.956   0.838  1.00  0.00           H  
HETATM   19  H   UNL     1       1.643   0.085  -1.865  1.00  0.00           H  
HETATM   20  H   UNL     1      -0.779  -1.028  -1.849  1.00  0.00           H  
HETATM   21  H   UNL     1      -1.180  -2.506  -0.942  1.00  0.00           H  
HETATM   22  H   UNL     1      -2.424  -2.216   1.171  1.00  0.00           H  
HETATM   23  H   UNL     1      -2.224   1.393  -1.699  1.00  0.00           H  
HETATM   24  H   UNL     1      -0.294   2.721   1.398  1.00  0.00           H  
CONECT    1    2   16                                                 
CONECT    2    1    3   17   18                                       
CONECT    3    2    4    5   13                                       
CONECT    4    3   19                                                 
CONECT    5    3    6                                                 
CONECT    6    5    7   20   21                                       
CONECT    7    6    8    9   10                                       
CONECT    8    7                                                      
CONECT    9    7   22                                                 
CONECT   10    7   11   12   13                                       
CONECT   11   10                                                      
CONECT   12   10   23                                                 
CONECT   13   10   14    3   15                                       
CONECT   14   13                                                      
CONECT   15   13   24                                                 
CONECT   16    1                                                      
CONECT   17    2                                                      
CONECT   18    2                                                      
CONECT   19    4                                                      
CONECT   20    6                                                      
CONECT   21    6                                                      
CONECT   22    9                                                      
CONECT   23   12                                                      
CONECT   24   15                                                      
MASTER        0    0    0    0    0    0    0    0   24    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
D-Lyxo-2-hexulose	HMDB
D-Lyxo-hex-2-ulose	HMDB
D-Tag	HMDB
Lyxo-2-hexulose	HMDB
Lyxo-hexulose	HMDB
Tagatose	HMDB
Tagatose, (D)-isomer	HMDB
Tagatose, (beta-D)-isomer	HMDB
Tagatose, (alpha-D)-isomer	HMDB
Tagatose, (DL)-isomer	HMDB
D-Tagatopyranose	HMDB
Tagatopyranose	HMDB
beta-D-Tagatopyranose	HMDB
beta-D-Tagatose	HMDB
Β-D-tagatopyranose	HMDB
Β-D-tagatose	HMDB
b-D-Tagatopyranose	HMDB
D-Tagatose	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.156

Monoisotopic Molecular Weight

180.063388106

IUPAC Name

(2R,3S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

Traditional Name

β-D-tagatopyranose

CAS Registry Number

20197-42-6

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 Key

LKDRXBCSQODPBY-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Oxane
Monosaccharide
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-tagatopyranose (CHEBI:49092 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.202	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	399 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.8	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M-H]-	Experimental	MetCCS_train_neg	129.772	30932474
AllCCS	[M-H]-	Experimental	Not Available	129.772	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000396

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
D-Tagatose,1TMS,#1	1752.9675	https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#2	1742.4346	https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#3	1751.6187	https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#4	1737.4463	https://arxiv.org/abs/1905.12712
D-Tagatose,1TMS,#5	1753.5137	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#1	1727.3402	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#2	1731.9012	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#3	1737.4377	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#4	1727.8997	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#5	1744.1982	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#6	1734.4967	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#7	1733.7573	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#8	1723.2323	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#9	1688.9996	https://arxiv.org/abs/1905.12712
D-Tagatose,2TMS,#10	1704.1431	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#1	1750.2974	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#2	1767.7611	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#3	1738.1187	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#4	1713.7587	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#5	1747.4048	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#6	1743.852	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#7	1741.2212	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#8	1733.3438	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#9	1754.151	https://arxiv.org/abs/1905.12712
D-Tagatose,3TMS,#10	1698.2463	https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#1	1780.2516	https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#2	1788.9886	https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#3	1828.2352	https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#4	1767.6804	https://arxiv.org/abs/1905.12712
D-Tagatose,4TMS,#5	1784.7595	https://arxiv.org/abs/1905.12712
D-Tagatose,5TMS,#1	1903.7284	https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#1	2006.5377	https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#2	2009.8174	https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#3	1988.6361	https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#4	1962.1846	https://arxiv.org/abs/1905.12712
D-Tagatose,1TBDMS,#5	1973.6067	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#1	2193.4688	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#2	2199.503	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#3	2185.5747	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#4	2185.439	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#5	2204.7117	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#6	2186.0137	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#7	2181.9297	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#8	2176.063	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#9	2151.4893	https://arxiv.org/abs/1905.12712
D-Tagatose,2TBDMS,#10	2159.538	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#1	2432.5461	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#2	2427.159	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#3	2413.2021	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#4	2419.6245	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#5	2436.7866	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#6	2430.6118	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#7	2421.9028	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#8	2431.1104	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#9	2428.2686	https://arxiv.org/abs/1905.12712
D-Tagatose,3TBDMS,#10	2409.5088	https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#1	2666.833	https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#2	2650.9458	https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#3	2647.7903	https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#4	2658.429	https://arxiv.org/abs/1905.12712
D-Tagatose,4TBDMS,#5	2658.8936	https://arxiv.org/abs/1905.12712
D-Tagatose,5TBDMS,#1	2868.984	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0uxs-0931000000-9deccc61a68dc8c51aa7	2019-05-23	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0uxr-0930000000-e1672ba6560efb925aa5	2019-05-23	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-0931000000-9deccc61a68dc8c51aa7	2019-05-23	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxr-0930000000-e1672ba6560efb925aa5	2019-05-23	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0920000000-c785d191926ead60dc63	2019-05-23	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-0930000000-0c79b52b64467170ea34	2019-05-23	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-1900000000-72ad7431e281814fc59a	2019-05-23	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kb-9000000000-ac1464fac3ca774eb08b	2019-05-23	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05mk-9000000000-4bc4673c212944cded87	2019-05-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-6900000000-def874fe6470032fdd27	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9100000000-b495c0f16251b5ee98e1	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-d526231c78d5ea2b9be5	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01pk-0900000000-d9de28ed437f1079125e	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-9700000000-21b6c695fb9bdd5ae08d	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-7c49e3a2d60cfed68a76	2021-09-08	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2019-05-23	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, H₂O, predicted)	2019-05-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001109

KNApSAcK ID

Not Available

Chemspider ID

10194220

KEGG Compound ID

C00795

BioCyc ID

D-tagatose

BiGG ID

Not Available

Wikipedia Link

Tagatose

METLIN ID

Not Available

PubChem Compound

14408225

PDB ID

Not Available

ChEBI ID

49092

Food Biomarker Ontology

Not Available

VMH ID

TAGAT_D

MarkerDB ID

Not Available

References

Synthesis Reference

Kim, 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

Oh DK: Tagatose: properties, applications, and biotechnological processes. Appl Microbiol Biotechnol. 2007 Aug;76(1):1-8. Epub 2007 May 10. [PubMed:17492284 ]
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 ]

Showing metabocard for D-Tagatose (HMDB0003418)

MOL for HMDB0003418 (D-Tagatose)

3D MOL for HMDB0003418 (D-Tagatose)

3D SDF for HMDB0003418 (D-Tagatose)

3D-SDF for HMDB0003418 (D-Tagatose)

PDB for HMDB0003418 (D-Tagatose)

3D PDB for HMDB0003418 (D-Tagatose)

SMILES for HMDB0003418 (D-Tagatose)

INCHI for HMDB0003418 (D-Tagatose)

Structure for HMDB0003418 (D-Tagatose)

3D Structure for HMDB0003418 (D-Tagatose)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR