Rhamnose

Identification

Name
Rhamnose
Accession Number
DB02961  (EXPT02795, DB01869)
Type
Small Molecule
Groups
Experimental
Description

A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. [PubChem]

Structure
Thumb
Synonyms
  • L-rhamnose
External IDs
FEMA NO. 3730
Categories
Not Available
UNII
QN34XC755A
CAS number
3615-41-6
Weight
Average: 164.1565
Monoisotopic: 164.068473494
Chemical Formula
C6H12O5
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UL-rhamnose isomeraseNot AvailableEscherichia 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
KEGG Compound
C00507
PubChem Compound
19233
PubChem Substance
46507432
ChemSpider
18150
ChEBI
16055
HET
RNS
Wikipedia
Rhamnose
PDB Entries
1de6 / 1x8d / 2i56 / 3itt / 3m0h / 3m0v / 3m0y / 4gji

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility258.0 mg/mLALOGPS
logP-2ALOGPS
logP-2.5ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.8 m3·mol-1ChemAxon
Polarizability15.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.904
Blood Brain Barrier+0.6505
Caco-2 permeable-0.8361
P-glycoprotein substrateNon-substrate0.6823
P-glycoprotein inhibitor INon-inhibitor0.9712
P-glycoprotein inhibitor IINon-inhibitor0.9665
Renal organic cation transporterNon-inhibitor0.9588
CYP450 2C9 substrateNon-substrate0.8163
CYP450 2D6 substrateNon-substrate0.9111
CYP450 3A4 substrateNon-substrate0.7357
CYP450 1A2 substrateNon-inhibitor0.8235
CYP450 2C9 inhibitorNon-inhibitor0.8432
CYP450 2D6 inhibitorNon-inhibitor0.9503
CYP450 2C19 inhibitorNon-inhibitor0.9466
CYP450 3A4 inhibitorNon-inhibitor0.8437
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9379
Ames testNon AMES toxic0.8425
CarcinogenicityNon-carcinogens0.5951
BiodegradationReady biodegradable0.8253
Rat acute toxicity1.3420 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9882
hERG inhibition (predictor II)Non-inhibitor0.9677
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)GC-MSsplash10-014i-0920000000-3f32654cd6b207d5192c
GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)GC-MSsplash10-014i-0910000000-3efed9ba21b4acc1a0a7
GC-MS Spectrum - EI-BGC-MSsplash10-014i-0920000000-15cadd38d19e98599380
GC-MS Spectrum - EI-BGC-MSsplash10-014i-0920000000-845777ce5ccb02564dd4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0910000000-a3998948f1f154365fea
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-09ff33efc7ead61776ac
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-3900000000-ff3539fb021325c23c4a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9200000000-b270b5d83d44008211ba
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-f516852459b277fdb157
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ly9-9600000000-efc90d58c6475abfcecd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0abi-9100000000-3b89500afd7b488df6fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-7b10fe17f3ce9401fd3f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-c17a9df600308d9b31be

Taxonomy

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
Hexose monosaccharide / Medium-chain aldehyde / Beta-hydroxy aldehyde / Alpha-hydroxyaldehyde / Secondary alcohol / Polyol / Organic oxide / Hydrocarbon derivative / Carbonyl group / Aldehyde
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
aldehyde, L-rhamnose (CHEBI:16055)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Manganese ion binding
Specific Function
Not Available
Gene Name
rhaA
Uniprot ID
P32170
Uniprot Name
L-rhamnose isomerase
Molecular Weight
47198.95 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:06