Showing Metabocard for L-rhamnopyranose (BASm0004268)
| Common Name | L-rhamnopyranose |
|---|---|
| Description | Rhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of certain bacteria. L-rhamnose is metabolized to L-Lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. It exists in two anomeric forms, alpha-L-rhamnose and beta-L-rhamnose. Rhamnose has been found in Klebsiella, Pseudomonas (https://link.springer.com/article/10.1007/BF00369505) (https://onlinelibrary.wiley.com/doi/abs/10.1002/ejlt.200300816). |
| Structure | |
| Molecular Formula | C6H12O5 |
| Average Mass | 164.15650 |
| Monoisotopic Mass | 164.06847 |
| IUPAC Name | (3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol |
| Traditional Name | (3r,4r,5r,6s)-6-methyloxane-2,3,4,5-tetrol |
| CAS Registry Number | 3615-41-6 |
| SMILES | C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O |
| InChI Identifier | InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6?/m0/s1 |
| InChI Key | SHZGCJCMOBCMKK-JFNONXLTSA-N |
| CHEBI ID | CHEBI:62346 |
| HMDB ID | HMDB0000849 |
| State | Solid |
| Water Solubility | 8.27e+02 g/l |
| logP | -2.39 |
| logS | 0.70 |
| pKa (Strongest Acidic) | 11.30 |
| pKa (Strongest Basic) | -3.61 |
| Hydrogen Acceptor Count | 5 |
| Hydrogen Donor Count | 4 |
| Polar Surface Area | 90.15 Ų |
| Rotatable Bond Count | 0 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 34.38 m³·mol⁻¹ |
| Polarizability | 15.09 |