alpha-L-fucose

Identification

Generic Name
alpha-L-fucose
DrugBank Accession Number
DB04473
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 164.1565
Monoisotopic: 164.068473494
Chemical Formula
C6H12O5
Synonyms
  • α-L-Fuc
  • α-L-fucose
  • α-L-Fucp

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot Available
UEnvelope glycoprotein gp160Not AvailableSIV-mac
UIg gamma-1 chain C regionNot AvailableHumans
UGenome polyproteinNot AvailableDENV-3
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
Not Available
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
Oxanes / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Hemiacetal / Hexose monosaccharide / Hydrocarbon derivative / Organoheterocyclic compound / Oxacycle / Oxane / Polyol / Secondary alcohol
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
L-fucopyranose (CHEBI:42548)
Affected organisms
Not Available

Chemical Identifiers

UNII
OF086I9H7W
CAS number
6696-41-9
InChI Key
SHZGCJCMOBCMKK-SXUWKVJYSA-N
InChI
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
IUPAC Name
(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
SMILES
C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O

References

General References
Not Available
PubChem Compound
439554
PubChem Substance
46504974
ChemSpider
388645
ChEBI
42548
ZINC
ZINC000001532814
PDBe Ligand
FUC
PDB Entries
1ah1 / 1ax0 / 1ax1 / 1ax2 / 1axy / 1axz / 1b0f / 1b41 / 1b5f / 1bcr
show 1925 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility827.0 mg/mLALOGPS
logP-2.4ALOGPS
logP-1.9Chemaxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area90.15 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity34.38 m3·mol-1Chemaxon
Polarizability15.21 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5618
Blood Brain Barrier+0.514
Caco-2 permeable-0.6509
P-glycoprotein substrateNon-substrate0.6253
P-glycoprotein inhibitor INon-inhibitor0.956
P-glycoprotein inhibitor IINon-inhibitor0.9917
Renal organic cation transporterNon-inhibitor0.9389
CYP450 2C9 substrateNon-substrate0.8017
CYP450 2D6 substrateNon-substrate0.887
CYP450 3A4 substrateNon-substrate0.7106
CYP450 1A2 substrateNon-inhibitor0.9489
CYP450 2C9 inhibitorNon-inhibitor0.9723
CYP450 2D6 inhibitorNon-inhibitor0.9736
CYP450 2C19 inhibitorNon-inhibitor0.9775
CYP450 3A4 inhibitorNon-inhibitor0.9227
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9502
Ames testNon AMES toxic0.8645
CarcinogenicityNon-carcinogens0.9321
BiodegradationReady biodegradable0.628
Rat acute toxicity1.4658 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9649
hERG inhibition (predictor II)Non-inhibitor0.9726
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00os-0900000000-2fd25b416f5022d25dd5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-5e9626749e20ae1bd20e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9600000000-bc55946922c083913fd9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0596-9100000000-b68b73d7078851964dd3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4u-9000000000-f302506ece1058fcb5ae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-9521539248f8e5260493
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]-132.7398684
predicted
DarkChem Lite v0.1.0
[M-H]-137.65947
predicted
DeepCCS 1.0 (2019)
[M+H]+135.2056684
predicted
DarkChem Lite v0.1.0
[M+H]+139.98146
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.4533684
predicted
DarkChem Lite v0.1.0
[M+Na]+146.61845
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
Envelope protein E binding to host cell surface receptor is followed by virus internalization through clathrin-mediated endocytosis. Envelope protein E is subsequently involved in membrane fusion b...
Gene Name
Not Available
Uniprot ID
P27914
Uniprot Name
Genome polyprotein
Molecular Weight
187438.87 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]
Kind
Protein
Organism
SIV-mac
Pharmacological action
Unknown
General Function
The surface protein gp120 (SU) attaches the virus to the host lymphoid cell by binding to the primary receptor CD4. This interaction induces a structural rearrangement creating a high affinity binding site for a chemokine coreceptor like CCR5. This peculiar 2 stage receptor-interaction strategy allows gp120 to maintain the highly conserved coreceptor-binding site in a cryptic conformation, protected from neutralizing antibodies. These changes are transmitted to the transmembrane protein gp41 and are thought to activate its fusogenic potential by unmasking its fusion peptide (By similarity).
Specific Function
Structural molecule activity
Gene Name
env
Uniprot ID
P05884
Uniprot Name
Envelope glycoprotein gp160
Molecular Weight
Not Available
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Immunoglobulin receptor binding
Specific Function
Not Available
Gene Name
IGHG1
Uniprot ID
P01857
Uniprot Name
Ig gamma-1 chain C region
Molecular Weight
36105.695 Da
Kind
Protein
Organism
DENV-3
Pharmacological action
Unknown
General Function
Structural molecule activity
Specific Function
Capsid protein C self-assembles to form an icosahedral capsid about 30 nm in diameter. The capsid encapsulates the genomic RNA.prM acts as a chaperone for envelope protein E during intracellular vi...
Gene Name
Not Available
Uniprot ID
P27915
Uniprot Name
Genome polyprotein
Molecular Weight
378060.625 Da

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