(1S,2R,3S,4R,5R)-2,3,4-trihydroxy-N-octyl-6-oxa-8-azabicyclo[3.2.1]octane-8-carbothioamide

Identification

Generic Name
(1S,2R,3S,4R,5R)-2,3,4-trihydroxy-N-octyl-6-oxa-8-azabicyclo[3.2.1]octane-8-carbothioamide
DrugBank Accession Number
DB08260
Background

(1S,2R,3S,4R,5R)-2,3,4-trihydroxy-N-octyl-6-oxa-8-azabicyclo[3.2.1]octane-8-carbothioamide is a solid. This compound belongs to the oxepanes. These are compounds containing an oxepane ring, which is an a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. This drug targets the protein beta-glucosidase A.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 332.459
Monoisotopic: 332.176978084
Chemical Formula
C15H28N2O4S
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-glucosidase ANot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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
Adverseeffects
Improve decision support & research outcomes
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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 oxepanes. These are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxepanes
Sub Class
Not Available
Direct Parent
Oxepanes
Alternative Parents
Piperidines / Oxazolidines / Thioureas / Secondary alcohols / Polyols / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LFSNQOFOMJLHIW-MEBFFEOJSA-N
InChI
InChI=1S/C15H28N2O4S/c1-2-3-4-5-6-7-8-16-15(22)17-10-9-21-14(17)13(20)12(19)11(10)18/h10-14,18-20H,2-9H2,1H3,(H,16,22)/t10-,11+,12-,13+,14+/m0/s1
IUPAC Name
(1S,2R,3S,4R,5R)-2,3,4-trihydroxy-N-octyl-6-oxa-8-azabicyclo[3.2.1]octane-8-carbothioamide
SMILES
[H][C@@]12CO[C@@]([H])(N1C(=S)NCCCCCCCC)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O

References

General References
Not Available
PubChem Compound
24963032
PubChem Substance
99444731
ChemSpider
25059175
ZINC
ZINC000053683045
PDBe Ligand
NCW
PDB Entries
2vrj

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 Solubility0.805 mg/mLALOGPS
logP1.31ALOGPS
logP1.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area85.19 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.5 m3·mol-1ChemAxon
Polarizability36.35 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6689
Blood Brain Barrier-0.9175
Caco-2 permeable-0.6606
P-glycoprotein substrateSubstrate0.6795
P-glycoprotein inhibitor INon-inhibitor0.7557
P-glycoprotein inhibitor IINon-inhibitor0.9789
Renal organic cation transporterNon-inhibitor0.8703
CYP450 2C9 substrateNon-substrate0.7933
CYP450 2D6 substrateNon-substrate0.7988
CYP450 3A4 substrateNon-substrate0.5217
CYP450 1A2 substrateNon-inhibitor0.7964
CYP450 2C9 inhibitorNon-inhibitor0.7546
CYP450 2D6 inhibitorNon-inhibitor0.8963
CYP450 2C19 inhibitorNon-inhibitor0.7602
CYP450 3A4 inhibitorNon-inhibitor0.9253
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9038
Ames testNon AMES toxic0.6331
CarcinogenicityNon-carcinogens0.9047
BiodegradationNot ready biodegradable0.6447
Rat acute toxicity2.4667 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9153
hERG inhibition (predictor II)Non-inhibitor0.6366
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

Targets

Drugtargets2
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Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Beta-glucosidase activity
Specific Function
Not Available
Gene Name
bglA
Uniprot ID
Q08638
Uniprot Name
Beta-glucosidase A
Molecular Weight
51548.055 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52