| Identification | Back Directory | [Name]
D-MANNOHEPTULOSE | [CAS]
3615-44-9 | [Synonyms]
Ai3-61577
Nsc 226836
MANNOHEPTULOSE
D-MANNOHEPTULOSE
Einecs 222-795-5
Mannoheptulose,D-
D-Mannoketoheptose
D-manno-2-heptulose
ALPHA-D-MANNOHEPTULOSE
D-Manno-heptulose (8ci)
D-MANNOHEPTULOSE USP/EP/BP
d-Manno-[UL-13C7]hept-2-ulose | [EINECS(EC#)]
222-795-5 | [Molecular Formula]
C7H14O7 | [MDL Number]
MFCD00037814 | [MOL File]
3615-44-9.mol | [Molecular Weight]
210.18 |
| Chemical Properties | Back Directory | [Melting point ]
148-150°C | [alpha ]
D20 +29° (c = 2 in H2O) | [Boiling point ]
628.0±55.0 °C(Predicted) | [density ]
1.645±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Methanol (Slightly), Water (Slightly) | [form ]
Solid | [pka]
11.86±0.20(Predicted) | [color ]
White to Off-White | [Optical Rotation]
+29 | [Merck ]
13,4686 | [BRN ]
1726433 | [InChI]
1S/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3-,4-,5+,6+,7?/m1/s1 | [InChIKey]
HAIWUXASLYEWLM-BWSJPXOBSA-N | [SMILES]
OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H](O)[C@@H]1O | [EPA Substance Registry System]
D-manno-2-Heptulose (3615-44-9) |
| Hazard Information | Back Directory | [Description]
D-Glucose is phosphorylated by glucokinase and three tissue-specific hexokinases to produce glucose-6-phosphate in humans. D-Mannoheptulose is a heptose that inhibits glucokinases and hexokinases from diverse organisms through competition with D-glucose (Ki = 0.25 mM). It blocks glucose oxidation and glucose-mediated insulin release from pancreatic islet cells. D-Mannoheptulose prevents the conversion of glucose to glucose-6-phosphate that can mediate the activation of the carbohydrate response element binding protein. By blocking glucose phosphorylation, D-mannoheptulose causes transient hyperglycemia in dogs when given at 1 g/kg but not at 8 mg/kg, although postprandial energy expenditure is increased at the lower dose. | [Chemical Properties]
White Solid | [Uses]
Mannoheptulose occurs naturally in avocado fruit. | [Definition]
ChEBI: D-keto-manno-heptulose is the open chain form of D-manno-heptulose. | [References]
[1] H G COORE P J R. Inhibition of glucose phosphorylation by mannoheptulose.[J]. Biochemical Journal, 1964, 91 1: 56-59. DOI: 10.1042/bj0910056
[2] S J ASHCROFT P J R. Enzymes of glucose metabolism in normal mouse pancreatic islets.[J]. Biochemical Journal, 1970, 119 1: 5-15. DOI: 10.1042/bj1190005
[3] N DAI. Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence.[J]. Plant Cell, 1999, 11 7: 1253-1266. DOI: 10.1105/tpc.11.7.1253
[4] S J ASHCROFT P J R L C Weerasinghe. Interrelationship of islet metabolism, adenosine triphosphate content and insulin release.[J]. Biochemical Journal, 1973, 132 2: 223-231. DOI: 10.1042/bj1320223
[5] DANIEL JOHNSON. Glucose-dependent modulation of insulin secretion and intracellular calcium ions by GKA50, a glucokinase activator.[J]. Diabetes, 2007, 56 6: 1694-1702. DOI: 10.2337/db07-0026
[6] MING V. LI . Glucose-6-phosphate mediates activation of the carbohydrate responsive binding protein (ChREBP)[J]. Biochemical and biophysical research communications, 2010, 395 3: Pages 395-400. DOI: 10.1016/j.bbrc.2010.04.028
[7] LESLIE L MCKNIGHT. Mannoheptulose has differential effects on fasting and postprandial energy expenditure and respiratory quotient in adult Beagle dogs fed diets of different macronutrient contents.[J]. Journal of Nutritional Science, 2014, 3: e17. DOI: 10.1017/jns.2014.17 |
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