Identification

Name
scyllo-inositol
Accession Number
DB03106  (EXPT01892, DB05987, DB11931)
Type
Small Molecule
Groups
Investigational
Description

An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction. Scyllitol has been investigated for the treatment of Alzheimer Disease.

Structure
Thumb
Synonyms
  • (1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol
  • 1,3,5/2,4,6-cyclohexanehexol
  • Cocositol
  • Quercinitol
  • Scyllitol
External IDs
AZD 103 / AZD-103 / ELND 005 / ELND-005 / ELND005
Categories
Not Available
UNII
1VS4X81277
CAS number
488-59-5
Weight
Average: 180.1559
Monoisotopic: 180.063388116
Chemical Formula
C6H12O6
InChI Key
CDAISMWEOUEBRE-CDRYSYESSA-N
InChI
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
IUPAC Name
(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlucosylceramidaseNot AvailableHuman
U1-phosphatidylinositol phosphodiesteraseNot AvailableBacillus cereus
UCDP-diacylglycerol--inositol 3-phosphatidyltransferase
inhibitor
Human
U1-phosphatidylinositol phosphodiesteraseNot AvailableListeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)
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

Abdul H. Faug, "Compound useful for the production of 3-deoxy-3-fluoro-myo-inositol." U.S. Patent US4937390, issued March, 1964.

US4937390
General References
Not Available
External Links
KEGG Compound
C06153
PubChem Compound
892
PubChem Substance
46505198
ChemSpider
10254646
ChEBI
10642
ChEMBL
CHEMBL468154
Therapeutic Targets Database
DNC000974
HET
2H3
PDB Entries
4n54

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2TerminatedPreventionColon Carcinoma / Dysplasia in Crohn Disease / Low Grade Dysplasia in Ulcerative Colitis / Rectal Carcinoma1
2Active Not RecruitingTreatmentInsulin Resistance / Periodontitis / Polycystic Ovaries Syndrome1
2CompletedPreventionBronchopulmonary Dysplasia (BPD) / Infant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Retinopathy of Prematurity1
2CompletedPreventionLung Cancer Non-Small Cell Cancer (NSCLC) / Squamous Lung Dysplasia1
2CompletedTreatmentAlzheimer's Disease (AD)3
2CompletedTreatmentDown Syndrome (DS)1
2TerminatedTreatmentBipolar 1 Disorder1
Not AvailableUnknown StatusTreatmentPolycystic Ovaries Syndrome1

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 Solubility485.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.8ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.78 m3·mol-1ChemAxon
Polarizability16.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8654
Blood Brain Barrier-0.5194
Caco-2 permeable-0.5533
P-glycoprotein substrateNon-substrate0.7394
P-glycoprotein inhibitor INon-inhibitor0.9633
P-glycoprotein inhibitor IINon-inhibitor0.9901
Renal organic cation transporterNon-inhibitor0.9282
CYP450 2C9 substrateNon-substrate0.8523
CYP450 2D6 substrateNon-substrate0.9081
CYP450 3A4 substrateNon-substrate0.7198
CYP450 1A2 substrateNon-inhibitor0.8485
CYP450 2C9 inhibitorNon-inhibitor0.9099
CYP450 2D6 inhibitorNon-inhibitor0.952
CYP450 2C19 inhibitorNon-inhibitor0.9641
CYP450 3A4 inhibitorNon-inhibitor0.8545
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9045
Ames testNon AMES toxic0.7623
CarcinogenicityNon-carcinogens0.8722
BiodegradationReady biodegradable0.5644
Rat acute toxicity1.6459 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.967
hERG inhibition (predictor II)Non-inhibitor0.9701
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 cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Cyclohexanols
Alternative Parents
Sugar alcohols / Cyclitols and derivatives / Polyols / Hydrocarbon derivatives
Substituents
Cyclohexanol / Sugar alcohol / Cyclitol or derivatives / Cyclic alcohol / Polyol / Hydrocarbon derivative / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
inositol (CHEBI:10642)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Not Available
Gene Name
GBA
Uniprot ID
P04062
Uniprot Name
Glucosylceramidase
Molecular Weight
59715.745 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]
Kind
Protein
Organism
Bacillus cereus
Pharmacological action
Unknown
General Function
Phosphoric diester hydrolase activity
Specific Function
Cleaves glycosylphosphatidylinositol (GPI) and phosphatidylinositol (PI) anchors but not PI phosphates.
Gene Name
Not Available
Uniprot ID
P14262
Uniprot Name
1-phosphatidylinositol phosphodiesterase
Molecular Weight
38108.93 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Manganese ion binding
Specific Function
Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due t...
Gene Name
CDIPT
Uniprot ID
O14735
Uniprot Name
CDP-diacylglycerol--inositol 3-phosphatidyltransferase
Molecular Weight
23538.47 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)
Pharmacological action
Unknown
General Function
Phosphoric diester hydrolase activity
Specific Function
Cleaves glycosylphosphatidylinositol (GPI) and phosphatidylinositol (PI) anchors but not PI phosphates. Important factor in pathogenesis, PI-PLC activity is present only in virulent listeria specie...
Gene Name
plcA
Uniprot ID
P34024
Uniprot Name
1-phosphatidylinositol phosphodiesterase
Molecular Weight
36317.61 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:08