Identification

Name
Fucitol
Accession Number
DB03815  (EXPT01465)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • L-Fucitol
External IDs
NSC-1957
Categories
UNII
961570X3WO
CAS number
13074-06-1
Weight
Average: 166.1724
Monoisotopic: 166.084123558
Chemical Formula
C6H14O5
InChI Key
SKCKOFZKJLZSFA-KCDKBNATSA-N
InChI
InChI=1S/C6H14O5/c1-3(8)5(10)6(11)4(9)2-7/h3-11H,2H2,1H3/t3-,4+,5+,6-/m0/s1
IUPAC Name
(2R,3S,4R,5S)-hexane-1,2,3,4,5-pentol
SMILES
[H][C@@](C)(O)[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O)CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UL-fucose isomeraseNot AvailableShigella flexneri
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Arthur L. Campbell, James R. Behling, Kevin A. Babiak, John S. Ng, Richard A. Mueller, George W. J. Fleet, "Synthesis of N-substituted 1,5-dideoxy-1,5-imino-L-fucitol derivatives." U.S. Patent US4910310, issued March 20, 1990.

US4910310
General References
Not Available
External Links
PubChem Compound
445724
PubChem Substance
46506405
ChemSpider
393279
HET
FOC
Wikipedia
Fucitol
PDB Entries
1fui / 3a9t / 4c21

Clinical Trials

Clinical Trials
Not Available

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 Solubility476.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.7ChemAxon
logS0.46ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.86 m3·mol-1ChemAxon
Polarizability16.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8365
Blood Brain Barrier-0.5311
Caco-2 permeable-0.8806
P-glycoprotein substrateNon-substrate0.6291
P-glycoprotein inhibitor INon-inhibitor0.9505
P-glycoprotein inhibitor IINon-inhibitor0.9621
Renal organic cation transporterNon-inhibitor0.9398
CYP450 2C9 substrateNon-substrate0.8187
CYP450 2D6 substrateNon-substrate0.8761
CYP450 3A4 substrateNon-substrate0.6935
CYP450 1A2 substrateNon-inhibitor0.871
CYP450 2C9 inhibitorNon-inhibitor0.9337
CYP450 2D6 inhibitorNon-inhibitor0.9371
CYP450 2C19 inhibitorNon-inhibitor0.9395
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.958
Ames testNon AMES toxic0.9049
CarcinogenicityNon-carcinogens0.7795
BiodegradationReady biodegradable0.9051
Rat acute toxicity0.5019 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9761
hERG inhibition (predictor II)Non-inhibitor0.9394
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Fatty alcohols / Secondary alcohols / Polyols / Primary alcohols / Hydrocarbon derivatives
Substituents
Hexose monosaccharide / Fatty alcohol / Fatty acyl / Secondary alcohol / Polyol / Hydrocarbon derivative / Primary alcohol / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Manganese ion binding
Specific Function
Converts the aldose L-fucose into the corresponding ketose L-fuculose.
Gene Name
fucI
Uniprot ID
P69923
Uniprot Name
L-fucose isomerase
Molecular Weight
64976.17 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 November 02, 2018 05:45