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Chemistry

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Also known as: 87-81-0, D-lyxo-hexulose, Lyxo-2-hexulose, 17598-81-1, Tagatose, d-, Naturlose

Molecular Formula

C₆H₁₂O₆

Molecular Weight

180.16 g/mol

InChI Key

BJHIKXHVCXFQLS-PQLUHFTBSA-N

FDA UNII

T7A20Y888Y

tagatose is a natural product found in Pogostemon cablin and Solanum lycopersicum with data available.

1 2D Structure

Tagatose

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

2.1.2 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

2.1.3 InChI Key

BJHIKXHVCXFQLS-PQLUHFTBSA-N

2.1.4 Canonical SMILES

C(C(C(C(C(=O)CO)O)O)O)O

2.1.5 Isomeric SMILES

C([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

T7A20Y888Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D-tagatose

2. Tagatose

3. Tagatose, (alpha-d)-isomer

4. Tagatose, (beta-d)-isomer

5. Tagatose, (d)-isomer

6. Tagatose, (dl)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 87-81-0

2. D-lyxo-hexulose

3. Lyxo-2-hexulose

4. 17598-81-1

5. Tagatose, D-

6. Naturlose

7. Keto-d-tagatose

8. Tagatose [nf]

9. Chebi:47693

10. T7a20y888y

11. Tagatose (nf)

12. Rel-(3s,4s,5r)-1,3,4,5,6-pentahydroxyhexan-2-one

13. Dl-tagatose

14. Einecs 201-772-3

15. Unii-t7a20y888y

16. Mfcd00134449

17. D-tagatose [mi]

18. D-tagatose [fcc]

19. Tagatose [mart.]

20. Tagatose [usp-rs]

21. Schembl4035

22. Tagatose, D- [ii]

23. Chembl1236183

24. Zinc2516866

25. D-(-)-tagatose, >=98.5%

26. S5387

27. D-(-)-tagatose, Analytical Standard

28. Akos015856492

29. Akos015902493

30. Ccg-266424

31. Db04936

32. Ncgc00248704-01

33. As-44378

34. Hy-42680

35. Cs-0028435

36. T1501

37. D09007

38. Wurcs=2.0/1,1,0/[ho112h]/1/

39. 134t449

40. Q414089

41. W-200517

42. Tagatose, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₂O₆
Molecular Weight	180.16 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	180.06338810 g/mol
Monoisotopic Mass	180.06338810 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	147
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Intended for use as a therapeutic adjunct in the treatment of type II diabetes.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oral 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.

5.2 MeSH Pharmacological Classification

Iron Chelating Agents

Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems. (See all compounds classified as Iron Chelating Agents.)

5.3 Absorption, Distribution and Excretion

Absorption

Only 15-20 percent of tagatose is absorbed in the small intestine.

5.4 Metabolism/Metabolites

Tagatose does not influence the level of blood glucose nor insulin levels.

5.5 Mechanism of Action

he 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.

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