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Identification
NameL-Rhamnose
Accession NumberDB02961  (DB01869, EXPT02795)
Typesmall molecule
Groupsexperimental
Description

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

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number3615-41-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
Chemical FormulaC6H12O5
InChI KeyInChIKey=PNNNRSAQSRJVSB-JGWLITMVSA-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-/m1/s1
IUPAC Name
(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyhexanal
SMILES
C[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassMonosaccharides
Direct parentHexoses
Alternative parentsSecondary Alcohols; 1,2-Diols; Polyamines; Enolates; Aldehydes
Substituents1,2-diol; secondary alcohol; polyol; enolate; polyamine; alcohol; aldehyde
Classification descriptionThis compound belongs to the hexoses. These are monosaccharides in which the sugar unit is a hexose.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.8432
CYP450 2D6 substrate Non-inhibitor 0.9503
CYP450 2C19 substrate Non-inhibitor 0.9466
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point122 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility2.58e+02 g/lALOGPS
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 area97.99ChemAxon
rotatable bond count4ChemAxon
refractivity35.8ChemAxon
polarizability15.3ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot 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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00507
PubChem Compound93579
PubChem Substance46507432
ChEBI16055
ChEMBL
HETRNS
WikipediaRhamnose
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. L-rhamnose isomerase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
L-rhamnose isomerase P32170 Details

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
  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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19