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

Identification

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Name
(5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-phenyl-1,6-dioxa-2-azaspiro[4.5]dec-2-ene-8,9,10-triol
Accession Number
DB08151
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 295.2879
Monoisotopic: 295.105587281
Chemical Formula
C14H17NO6
InChI Key
YLTDNVVQKRHCJP-RKQHYHRCSA-N
InChI
InChI=1S/C14H17NO6/c16-7-10-11(17)12(18)13(19)14(20-10)6-9(15-21-14)8-4-2-1-3-5-8/h1-5,10-13,16-19H,6-7H2/t10-,11-,12+,13-,14-/m1/s1
IUPAC Name
(5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-phenyl-1,6-dioxa-2-azaspiro[4.5]dec-2-ene-8,9,10-triol
SMILES
[H][C@]1(CO)O[C@@]2(CC(=NO2)C2=CC=CC=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
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
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

General References
Not Available
External Links
PubChem Compound
44263483
PubChem Substance
99444622
ChemSpider
24648469
BindingDB
34108
ChEMBL
CHEMBL594972
HET
M08
PDB Entries
2qrh

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 Solubility9.04 mg/mLALOGPS
logP-0.7ALOGPS
logP-0.32ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)12.05ChemAxon
pKa (Strongest Basic)3.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area111.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.67 m3·mol-1ChemAxon
Polarizability29.48 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9068
Blood Brain Barrier+0.5511
Caco-2 permeable-0.6822
P-glycoprotein substrateNon-substrate0.5834
P-glycoprotein inhibitor INon-inhibitor0.8955
P-glycoprotein inhibitor IINon-inhibitor0.9576
Renal organic cation transporterNon-inhibitor0.7342
CYP450 2C9 substrateNon-substrate0.8217
CYP450 2D6 substrateNon-substrate0.8033
CYP450 3A4 substrateSubstrate0.5172
CYP450 1A2 substrateNon-inhibitor0.8358
CYP450 2C9 inhibitorNon-inhibitor0.8301
CYP450 2D6 inhibitorNon-inhibitor0.8802
CYP450 2C19 inhibitorNon-inhibitor0.8345
CYP450 3A4 inhibitorNon-inhibitor0.9625
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9395
Ames testNon AMES toxic0.6501
CarcinogenicityNon-carcinogens0.905
BiodegradationNot ready biodegradable0.7977
Rat acute toxicity2.4401 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9792
hERG inhibition (predictor II)Non-inhibitor0.8555
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 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
Oxanes / Monosaccharides / Benzene and substituted derivatives / Isoxazolines / Secondary alcohols / Polyols / Oxacyclic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds
show 2 more
Substituents
C-glycosyl compound / Monocyclic benzene moiety / Monosaccharide / Oxane / Benzenoid / Isoxazoline / Secondary alcohol / Oxacycle / Azacycle / Polyol
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:10592235]

Drug created on September 15, 2010 15:28 / Updated on August 02, 2019 08:19