Showing Metabocard for 6-phospho-D-glucono-1,5-lactone (BASm0003084)
| Common Name | 6-phospho-d-glucono-1,5-lactone | ||||
|---|---|---|---|---|---|
| Description | 6-phosphoglucono-delta-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. (PMID 3711719 ). The pentose-phosphate pathway provides reductive power and nucleotide precursors to the cell through oxidative and nonoxidative branches. 6-Phosphogluconolactonase is the second enzyme of the oxidative branch and catalyzes the hydrolysis of 6-phosphogluconolactones, the products of glucose 6-phosphate oxidation by glucose-6-phosphate dehydrogenase. By efficiently catalyzing the hydrolysis of d-6PGL, 6-phosphogluconolactonase prevents the reaction between d-6PGL and intracellular nucleophiles; such a reaction would interrupt the functioning of the pentose-phosphate pathway. (PMID 11457850 ). | ||||
| Structure | |||||
| Molecular Formula | C6H11O9P | ||||
| Average Mass | 258.11990 | ||||
| Monoisotopic Mass | 258.01407 | ||||
| IUPAC Name | {[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid | ||||
| Traditional Name | [(2r,3s,4s,5r)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxyphosphonic acid | ||||
| CAS Registry Number | 2641-81-8 | ||||
| SMILES | O=C1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H](O)[C@H]1O | ||||
| InChI Identifier | InChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1 | ||||
| InChI Key | IJOJIVNDFQSGAB-SQOUGZDYSA-N | ||||
| CHEBI ID | CHEBI:57955 | ||||
| HMDB ID | HMDB0001127 | ||||
| Pathways |
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| State | Solid | ||||
| Water Solubility | 3.26e+01 g/l | ||||
| logP | -1.99 | ||||
| logS | -0.90 | ||||
| pKa (Strongest Acidic) | 1.30 | ||||
| pKa (Strongest Basic) | -3.66 | ||||
| Hydrogen Acceptor Count | 7 | ||||
| Hydrogen Donor Count | 5 | ||||
| Polar Surface Area | 153.75 Ų | ||||
| Rotatable Bond Count | 3 | ||||
| Physiological Charge | -2 | ||||
| Formal Charge | 0 | ||||
| Refractivity | 45.65 m³·mol⁻¹ | ||||
| Polarizability | 19.89 |