(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(2-naphthyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol

Identification

Generic Name
(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(2-naphthyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol
DrugBank Accession Number
DB08500
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 347.3624
Monoisotopic: 347.136887409
Chemical Formula
C18H21NO6
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
UGlycogen phosphorylase, muscle formNot AvailableHumans
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
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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 c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glycosyl compounds
Alternative Parents
Phenylisoxazolidines / Naphthalenes / Azaspirodecane derivatives / Oxanes / Monosaccharides / Secondary alcohols / Polyols / Oxacyclic compounds / N-organohydroxylamines / Azacyclic compounds
show 3 more
Substituents
Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azaspirodecane / Benzenoid / C-glycosyl compound / Hydrocarbon derivative / Isoxazolidine / Monosaccharide / N-organohydroxylamine
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZCJBDRSKHARECB-PYTCMNEWSA-N
InChI
InChI=1S/C18H21NO6/c20-9-14-15(21)16(22)17(23)18(24-14)8-13(19-25-18)12-6-5-10-3-1-2-4-11(10)7-12/h1-7,13-17,19-23H,8-9H2/t13-,14+,15+,16-,17+,18+/m0/s1
IUPAC Name
(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(naphthalen-2-yl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol
SMILES
[H][C@]1(C[C@]2(ON1)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)C1=CC2=CC=CC=C2C=C1

References

General References
Not Available
PubChem Compound
46937156
PubChem Substance
99444971
ChemSpider
25058635
ZINC
ZINC000038965477
PDBe Ligand
S06
PDB Entries
2qrp

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 Solubility4.45 mg/mLALOGPS
logP0.14ALOGPS
logP0.55ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.07ChemAxon
pKa (Strongest Basic)4.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area111.41 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.64 m3·mol-1ChemAxon
Polarizability34.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9589
Blood Brain Barrier+0.5082
Caco-2 permeable-0.6926
P-glycoprotein substrateNon-substrate0.5665
P-glycoprotein inhibitor INon-inhibitor0.9209
P-glycoprotein inhibitor IINon-inhibitor0.9776
Renal organic cation transporterNon-inhibitor0.8815
CYP450 2C9 substrateNon-substrate0.8627
CYP450 2D6 substrateNon-substrate0.7889
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8524
CYP450 2C9 inhibitorNon-inhibitor0.861
CYP450 2D6 inhibitorNon-inhibitor0.8525
CYP450 2C19 inhibitorNon-inhibitor0.8421
CYP450 3A4 inhibitorNon-inhibitor0.9591
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8664
Ames testNon AMES toxic0.5895
CarcinogenicityNon-carcinogens0.9196
BiodegradationNot ready biodegradable0.9745
Rat acute toxicity2.5677 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9545
hERG inhibition (predictor II)Non-inhibitor0.7875
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/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
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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 on September 15, 2010 21:32 / Updated on June 12, 2020 16:52