L-Rhamnopyranose
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Basic Info
| Common Name | L-Rhamnopyranose(F00391) |
| 2D Structure | |
| FRCD ID | F00391 |
| CAS Number | |
| PubChem CID | 25310 |
| Formula | C6H12O5 |
| IUPAC Name | (3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol |
| InChI Key | SHZGCJCMOBCMKK-JFNONXLTSA-N |
| InChI | 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 |
| Canonical SMILES | CC1C(C(C(C(O1)O)O)O)O |
| Isomeric SMILES | C[C@H]1[C@@H]([C@H]([C@H](C(O1)O)O)O)O |
| Synonyms |
L-Rhamnose
Rhamnose
L-Rhamnopyranose
6-Deoxy-L-Mannopyranose
6-Deoxy-L-Mannose
L-(+)-RHAMNOSE
L-Rha
Rhamnopyranose
6-Deoxy-Mannose
CHEBI:62346
|
| Classifies |
Predicted: Animal Toxin
|
| Update Date | Nov 13, 2018 16:48 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Monosaccharides |
| Direct Parent | Hexoses |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Hexose monosaccharide - Oxane - Secondary alcohol - Hemiacetal - Oxacycle - Organoheterocyclic compound - Polyol - Hydrocarbon derivative - Alcohol - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 164.157 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Complexity | 139 |
| Monoisotopic Mass | 164.068 |
| Exact Mass | 164.068 |
| XLogP | -2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.5140 |
| Human Intestinal Absorption | HIA- | 0.5618 |
| Caco-2 Permeability | Caco2- | 0.6509 |
| P-glycoprotein Substrate | Non-substrate | 0.6253 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9560 |
| Non-inhibitor | 0.9917 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9389 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6188 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8017 |
| CYP450 2D6 Substrate | Non-substrate | 0.8870 |
| CYP450 3A4 Substrate | Non-substrate | 0.7106 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9489 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9723 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9736 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9775 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9227 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9502 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9649 |
| Non-inhibitor | 0.9726 | |
| AMES Toxicity | Non AMES toxic | 0.8645 |
| Carcinogens | Non-carcinogens | 0.9321 |
| Fish Toxicity | Low FHMT | 0.8979 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8033 |
| Honey Bee Toxicity | High HBT | 0.6938 |
| Biodegradation | Ready biodegradable | 0.6280 |
| Acute Oral Toxicity | III | 0.5590 |
| Carcinogenicity (Three-class) | Non-required | 0.6951 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.0392 | LogS |
| Caco-2 Permeability | -0.1358 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4658 | LD50, mol/kg |
| Fish Toxicity | 2.5783 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.1746 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Modifications of cell wall pectin in chilling-injured 'Friar' plum fruitsubjected to intermediate storage temperatures. | Food Chem | 2018 Mar 1 | 29037727 |
| Lectin Isolated from Japanese Red Sword Beans (Canavalia gladiata) as a PotentialCancer Chemopreventive Agent. | J Food Sci | 2018 Mar | 29437230 |
| Structural, functional, and biological properties of potato peeloligosaccharides. | Int J Biol Macromol | 2018 Jun | 29408417 |
| Polysaccharides obtained from bamboo shoots (Chimonobambusa quadrangularis)processing by-products: New insight into ethanol precipitation andcharacterization. | Int J Biol Macromol | 2018 Jun | 29425874 |
| Ultrasonic extraction, structural characterization, physicochemical propertiesand antioxidant activities of polysaccharides from bamboo shoots (Chimonobambusa quadrangularis) processing by-products. | Int J Biol Macromol | 2018 Jun | 29408482 |
| C-source metabolic profilings of foodborne Shiga-toxin producing E. coli match serogroup differentiations and highlight functional adaptations. | Int J Food Microbiol | 2018 Feb 2 | 29217302 |
| Chemical composition of Cyclocarya paliurus polysaccharide and inflammatory effects in lipopolysaccharide-stimulated RAW264.7 macrophage. | Int J Biol Macromol | 2018 Feb | 29032210 |
| Immunomodulatory acidic polysaccharides from Zizyphus jujuba cv. Huizao: Insightsinto their chemical characteristics and modes of action. | Food Chem | 2018 Aug 30 | 29655744 |
| Characteristics and intestinal immunomodulating activities of water-solublepectic polysaccharides from Chenpi with different storage periods. | J Sci Food Agric | 2018 Aug | 29330852 |
| Anti-fatigue activity of an arabinan-rich pectin from acerola (Malpighiaemarginata). | Int J Biol Macromol | 2018 Apr 1 | 29157904 |
| Extraction, structure, and emulsifying properties of pectin from potato pulp. | Food Chem | 2018 Apr 1 | 29120771 |
| Characterization of a thermostable recombinant l-rhamnose isomerase fromCaldicellulosiruptor obsidiansis OB47 and its application for the production ofl-fructose and l-rhamnulose. | J Sci Food Agric | 2018 Apr | 28960307 |
| Changes in pectin characteristics during the ripening of jujube fruit. | J Sci Food Agric | 2017 Sep | 28230255 |
| Ultrasonic degradation of sweet potato pectin and its antioxidant activity. | Ultrason Sonochem | 2017 Sep | 27617769 |
| Purification, Characterization, and Antioxidant Activity of PolysaccharidesIsolated from Cortex Periplocae. | Molecules | 2017 Oct 31 | 29088064 |
| Structural, functional and pH sensitive release characteristics of water-soluble polysaccharide from the seeds of Albizia lebbeck L. | Carbohydr Polym | 2017 Nov 1 | 28917894 |
| Structural elucidation of a pectin-type polysaccharide from Hovenia dulcispeduncles and its proliferative activity on RAW264.7 cells. | Int J Biol Macromol | 2017 Nov | 28715863 |
| Isolation of a lectin binding rhamnogalacturonan-I containing pecticpolysaccharide from pumpkin. | Carbohydr Polym | 2017 May 1 | 28267513 |
| Husk Tomato (Physalis ixocarpa Brot.) Waste as a Promising Source of Pectin:Extraction and Physicochemical Characterization. | J Food Sci | 2017 Jul | 28585703 |
| Opuntia dillenii (Ker-Gawl) Haw cladode mucilage: Physico-chemical, rheologicaland functional behavior. | Carbohydr Polym | 2017 Feb 10 | 27987807 |