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Identification
NameL-Rhamnose
Accession NumberDB02961  (EXPT02795, DB01869)
TypeSmall Molecule
GroupsExperimental
DescriptionA methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIO654621E3T
CAS number3615-41-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
Chemical FormulaC6H12O5
InChI KeyPNNNRSAQSRJVSB-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)[[email protected]](O)[C@@H](O)C=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
L-rhamnose isomeraseProteinunknownNot AvailableEscherichia coli (strain K12)P32170 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point122 °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
Polarizability15.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassAldehydes
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Monosaccharide
  • Saccharide
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23