Identification
NameRhamnose
Accession NumberDB02961  (EXPT02795, DB01869)
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
Synonyms
L-rhamnose
External IDs FEMA NO. 3730
Product Ingredients 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
CategoriesNot Available
UNIIQN34XC755A
CAS number3615-41-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
Chemical FormulaC6H12O5
InChI KeyPNNNRSAQSRJVSB-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
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not 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
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-014i-0920000000-3f32654cd6b207d5192cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-014i-0910000000-3efed9ba21b4acc1a0a7View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-0920000000-15cadd38d19e98599380View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-0920000000-845777ce5ccb02564dd4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-0910000000-a3998948f1f154365feaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-0900000000-09ff33efc7ead61776acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c17a9df600308d9b31beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-ff3539fb021325c23c4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9200000000-b270b5d83d44008211baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f516852459b277fdb157View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ly9-9600000000-efc90d58c6475abfcecdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9100000000-3b89500afd7b488df6faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7b10fe17f3ce9401fd3fView in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentHexoses
Alternative ParentsMedium-chain aldehydes / Beta-hydroxy aldehydes / Alpha-hydroxyaldehydes / Secondary alcohols / Polyols / Organic oxides / Hydrocarbon derivatives
SubstituentsHexose monosaccharide / Medium-chain aldehyde / Beta-hydroxy aldehyde / Alpha-hydroxyaldehyde / Secondary alcohol / Polyol / Organic oxide / Hydrocarbon derivative / Carbonyl group / Aldehyde
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsaldehyde, 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
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 June 23, 2017 10:18