Rhamnose
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Identification
- Generic Name
- Rhamnose
- DrugBank Accession Number
- DB02961
- Background
A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 164.1565
Monoisotopic: 164.068473494 - Chemical Formula
- C6H12O5
- Synonyms
- L-rhamnose
- External IDs
- FEMA NO. 3730
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UL-rhamnose isomerase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Hexoses
- Alternative Parents
- Medium-chain aldehydes / Beta-hydroxy aldehydes / Alpha-hydroxyaldehydes / Secondary alcohols / Polyols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aldehyde / Aliphatic acyclic compound / Alpha-hydroxyaldehyde / Beta-hydroxy aldehyde / Carbonyl group / Hexose monosaccharide / Hydrocarbon derivative / Medium-chain aldehyde / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- aldehyde, L-rhamnose (CHEBI:16055)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- QN34XC755A
- CAS number
- 3615-41-6
- InChI Key
- PNNNRSAQSRJVSB-BXKVDMCESA-N
- InChI
- InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
- IUPAC Name
- (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
- SMILES
- [H][C@@](C)(O)[C@]([H])(O)[C@@]([H])(O)[C@@]([H])(O)C=O
References
- Synthesis Reference
Peter S. J. Cheetham, Michael A. Quail, "Process for preparing L-rhamnose." U.S. Patent US5077206, issued May, 1975.
US5077206- General References
- Not Available
- External Links
- PDB Entries
- 1de6 / 1x8d / 2i56 / 3itt / 3m0h / 3m0v / 3m0y / 4gji
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 122 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 258.0 mg/mL ALOGPS logP -2 ALOGPS logP -2.5 Chemaxon logS 0.2 ALOGPS pKa (Strongest Acidic) 12.31 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 97.99 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 35.8 m3·mol-1 Chemaxon Polarizability 15.24 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.904 Blood Brain Barrier + 0.6505 Caco-2 permeable - 0.8361 P-glycoprotein substrate Non-substrate 0.6823 P-glycoprotein inhibitor I Non-inhibitor 0.9712 P-glycoprotein inhibitor II Non-inhibitor 0.9665 Renal organic cation transporter Non-inhibitor 0.9588 CYP450 2C9 substrate Non-substrate 0.8163 CYP450 2D6 substrate Non-substrate 0.9111 CYP450 3A4 substrate Non-substrate 0.7357 CYP450 1A2 substrate Non-inhibitor 0.8235 CYP450 2C9 inhibitor Non-inhibitor 0.8432 CYP450 2D6 inhibitor Non-inhibitor 0.9503 CYP450 2C19 inhibitor Non-inhibitor 0.9466 CYP450 3A4 inhibitor Non-inhibitor 0.8437 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9379 Ames test Non AMES toxic 0.8425 Carcinogenicity Non-carcinogens 0.5951 Biodegradation Ready biodegradable 0.8253 Rat acute toxicity 1.3420 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9882 hERG inhibition (predictor II) Non-inhibitor 0.9677
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 136.6409684 predictedDarkChem Lite v0.1.0 [M-H]- 136.0626684 predictedDarkChem Lite v0.1.0 [M-H]- 134.8032 predictedDeepCCS 1.0 (2019) [M+H]+ 138.4475684 predictedDarkChem Lite v0.1.0 [M+H]+ 137.5216684 predictedDarkChem Lite v0.1.0 [M+H]+ 137.19601 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.6115684 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.74889 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsL-rhamnose isomerase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the interconversion of L-rhamnose and L-rhamnulose (PubMed:14243758, PubMed:1650346, PubMed:2558952, PubMed:8564401). Can also catalyze the isomerization of L-lyxose to L-xylulose (PubMed:1650346).
- Specific Function
- identical protein binding
- Gene Name
- rhaA
- Uniprot ID
- P32170
- Uniprot Name
- L-rhamnose isomerase
- Molecular Weight
- 47198.95 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52