Showing Metabocard for L-gulono-1,4-lactone (BASm0001013)
| Common Name | L-gulono-1,4-lactone |
|---|---|
| Description | L-Gulonolactone (also known as reduced ascorbic acid, RAA) is the substrate of the enzyme L-gulono-1,4-lactone oxidoreductase (EC 1.1.3.8), which catalyzes the last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals. The enzyme L-Gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans. L-Gulonolactone is present in human blood and has been used as one of the markers to compare changes in exercise-induced oxidative stress. (PMID:16956367 , 16494601 ). |
| Structure | |
| Molecular Formula | C6H10O6 |
| Average Mass | 178.14000 |
| Monoisotopic Mass | 178.04774 |
| IUPAC Name | (3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one |
| Traditional Name | L-gulono-1,4-lactone |
| CAS Registry Number | 1128-23-0 |
| SMILES | O=C1O[C@H]([C@@H](O)CO)[C@H](O)[C@@H]1O |
| InChI Identifier | InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1 |
| InChI Key | SXZYCXMUPBBULW-SKNVOMKLSA-N |
| CHEBI ID | CHEBI:17587 |
| HMDB ID | HMDB0003466 |
| State | Not Available |
| Water Solubility | 6.37e+02 g/l |
| logP | -2.05 |
| logS | 0.55 |
| pKa (Strongest Acidic) | 11.62 |
| pKa (Strongest Basic) | -2.97 |
| Hydrogen Acceptor Count | 5 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 107.22 Ų |
| Rotatable Bond Count | 2 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 34.78 m³·mol⁻¹ |
| Polarizability | 15.56 |