NAV

Rhamnose

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
3D
Similar Structures
Weight
Average: 164.1565
Monoisotopic: 164.068473494
Chemical Formula
C6H12O5
Synonyms
  • L-rhamnose
External IDs
  • FEMA NO. 3730
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Pharmacology

Indication

Not Available

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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

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
KEGG Compound
C00507
PubChem Compound
19233
PubChem Substance
46507432
ChemSpider
18150
RxNav
1872246
ChEBI
16055
ZINC
ZINC000002038606
PDBe Ligand
RNS
Wikipedia
Rhamnose
PDB Entries
1de6 / 1x8d / 2i56 / 3itt / 3m0h / 3m0v / 3m0y / 4gji

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedScreeningInfants, Premature / Intestinal Permeability1
0CompletedDiagnosticCrohn's Disease (CD)1

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)12.31Chemaxon
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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-c17a9df600308d9b31be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2900000000-7beae0d1b67501fcb819
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-9300000000-d8665ec56300b843aef8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0adi-9100000000-1352cae092fb635a679b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-9000000000-d4dc17807a67e32ab31f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006y-9000000000-252ac3ef76a19fc26d87
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-9000000000-3aa9f6c350d846f38146
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.6409684
predicted
DarkChem Lite v0.1.0
[M-H]-136.0626684
predicted
DarkChem Lite v0.1.0
[M-H]-134.8032
predicted
DeepCCS 1.0 (2019)
[M+H]+138.4475684
predicted
DarkChem Lite v0.1.0
[M+H]+137.5216684
predicted
DarkChem Lite v0.1.0
[M+H]+137.19601
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.6115684
predicted
DarkChem Lite v0.1.0
[M+Na]+143.74889
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. L-rhamnose isomerase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52