NAV

Fucitol

Identification

Generic Name
Fucitol
DrugBank Accession Number
DB03815
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 166.1724
Monoisotopic: 166.084123558
Chemical Formula
C6H14O5
Synonyms
  • L-Fucitol
External IDs
  • NSC-1957
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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

Chemical Identifiers

UNII
961570X3WO
CAS number
13074-06-1
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

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
PubChem Compound
445724
PubChem Substance
46506405
ChemSpider
393279
ZINC
ZINC000002575033
PDBe Ligand
FOC
Wikipedia
Fucitol
PDB Entries
1fui / 3a9t / 4c21

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 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-MSsplash10-08i4-9200000000-3a42655db4c6b3b25ee1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-9826dd0380346c0e364c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9100000000-5821fd98154b50b3c9c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-90efae42f7cbe9e97263
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-cba8ab24fdfbb7504690
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-9000000000-dc804bd2f8ea23f9d244
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-8a9712a5a1633a32cdec
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]-136.8048546
predicted
DarkChem Lite v0.1.0
[M-H]-137.72076
predicted
DeepCCS 1.0 (2019)
[M+H]+137.3993546
predicted
DarkChem Lite v0.1.0
[M+H]+140.07635
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.7853546
predicted
DarkChem Lite v0.1.0
[M+Na]+146.4788
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. L-fucose isomerase
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. [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