Showing Metabocard for D-xylono-1,5-lactone (BASm0000448)
| Common Name | D-xylono-1,5-lactone |
|---|---|
| Description | D-xylonolactone is a lactone derivative of xylonic acid. It is an intermediate in the pentose and glucuronate interconversion pathway and can be formed from either D-xylonic acid or D-xylose. D-xylose is a simple 5 carbon sugar that is found in a variety of edible plants. It is also frequently used in intestinal absorption tests to help diagnose problems that prevent the small intestine from absorbing nutrients in food. Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation and so it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate. D-xylose is normally easily absorbed by the intestines where it can be converted to D-xylonolactone by intestinal D-xylose 1-dehydrogenase (EC 1.1.1.175). |
| Structure | |
| Molecular Formula | C5H8O5 |
| Average Mass | 148.11400 |
| Monoisotopic Mass | 148.03717 |
| IUPAC Name | (3R,4S,5R)-3,4,5-trihydroxyoxan-2-one |
| Traditional Name | D-xylono-1,5-lactone |
| CAS Registry Number | Not Available |
| SMILES | O=C1OC[C@@H](O)[C@H](O)[C@H]1O |
| InChI Identifier | InChI=1S/C5H8O5/c6-2-1-10-5(9)4(8)3(2)7/h2-4,6-8H,1H2/t2-,3+,4-/m1/s1 |
| InChI Key | XXBSUZSONOQQGK-FLRLBIABSA-N |
| CHEBI ID | CHEBI:15867 |
| HMDB ID | HMDB0011676 |
| State | Solid |
| Water Solubility | 8.30e+02 g/l |
| logP | -2.09 |
| logS | 0.75 |
| pKa (Strongest Acidic) | 11.63 |
| pKa (Strongest Basic) | -3.54 |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 3 |
| Polar Surface Area | 86.99 Ų |
| Rotatable Bond Count | 0 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 28.82 m³·mol⁻¹ |
| Polarizability | 12.53 |