Record Information |
---|
Version | 2.0 |
---|
Created at | 2017-03-23 03:12:34 UTC |
---|
Updated at | 2021-10-07 20:38:22 UTC |
---|
NP-MRD ID | NP0000751 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Fructose-1P |
---|
Description | Fructose 1-phosphate, also known as D-fructose-1-p, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Metabolism of fructose thus essentially results in intermediates of glycolysis. The final product of glycolysis (pyruvate) may then undergo gluconeogenesis, enter the TCA cycle or be stored as fatty acids. Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, fructose 1-phosphate participates in a number of enzymatic reactions. In particular, fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. Because fructokinase has a high Vmax fructose entering cells is quickly phosphorylated to fructose 1-phosphate. In humans, fructose 1-phosphate is involved in fructose intolerance, hereditary. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It is generated mainly by hepatic fructokinase but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule. Aldolase B converts it into glyceraldehyde and dihydroxyacetone phosphate (DHAP). Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness. |
---|
Structure | OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1 |
---|
Synonyms | Value | Source |
---|
beta-D-Fructose 1-phosphate | ChEBI | b-D-Fructose 1-phosphate | Generator | b-D-Fructose 1-phosphoric acid | Generator | beta-D-Fructose 1-phosphoric acid | Generator | Β-D-fructose 1-phosphate | Generator | Β-D-fructose 1-phosphoric acid | Generator | Fructose 1-phosphoric acid | Generator | D-Fructose 1-phosphate | HMDB | D-Fructose-1-p | HMDB | D-Fructose-1-phosphate | HMDB | Fructose-1-p | HMDB | Fructose-1-phosphate | HMDB | b-D-Fructofuranose 1-phosphate | HMDB | b-D-Fructofuranose 1-phosphoric acid | HMDB | beta-D-Fructofuranose 1-phosphoric acid | HMDB | Β-D-fructofuranose 1-phosphate | HMDB | Β-D-fructofuranose 1-phosphoric acid | HMDB |
|
---|
Chemical Formula | C6H12O6 |
---|
Average Mass | 180.1559 Da |
---|
Monoisotopic Mass | 180.06339 Da |
---|
IUPAC Name | {[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid |
---|
Traditional Name | [(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid |
---|
CAS Registry Number | 57-48-7 |
---|
SMILES | [H][C@@](O)(CO)[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 Key | BJHIKXHVCXFQLS-UYFOZJQFSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Species Where Detected | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Hexose phosphates |
---|
Alternative Parents | |
---|
Substituents | - Hexose phosphate
- Pentose phosphate
- Pentose-5-phosphate
- C-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Primary alcohol
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 399 g/l | Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/) | LogP | -2.23 | Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/) |
|
---|
Predicted Properties | |
---|