NAV

(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methylphenyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol

Identification

Generic Name
(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methylphenyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol
DrugBank Accession Number
DB08503
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 311.3303
Monoisotopic: 311.136887409
Chemical Formula
C15H21NO6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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 / Azaspirodecane derivatives / Toluenes / 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 / Monocyclic benzene moiety / Monosaccharide
show 12 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
HRCKGDOSPBFICB-MZHQWRCYSA-N
InChI
InChI=1S/C15H21NO6/c1-8-2-4-9(5-3-8)10-6-15(22-16-10)14(20)13(19)12(18)11(7-17)21-15/h2-5,10-14,16-20H,6-7H2,1H3/t10-,11+,12+,13-,14+,15+/m0/s1
IUPAC Name
(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methylphenyl)-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=CC=C(C)C=C1

References

General References
Not Available
PubChem Compound
46937157
PubChem Substance
99444974
ChemSpider
25059099
ZINC
ZINC000038965475
PDBe Ligand
S13
PDB Entries
2qrq

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 Solubility27.9 mg/mLALOGPS
logP-0.33ALOGPS
logP0.078Chemaxon
logS-1ALOGPS
pKa (Strongest Acidic)12.07Chemaxon
pKa (Strongest Basic)3.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area111.41 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity86.24 m3·mol-1Chemaxon
Polarizability31.38 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9309
Blood Brain Barrier-0.7356
Caco-2 permeable-0.6815
P-glycoprotein substrateNon-substrate0.5171
P-glycoprotein inhibitor INon-inhibitor0.8813
P-glycoprotein inhibitor IINon-inhibitor0.9887
Renal organic cation transporterNon-inhibitor0.883
CYP450 2C9 substrateNon-substrate0.8091
CYP450 2D6 substrateNon-substrate0.7921
CYP450 3A4 substrateSubstrate0.5114
CYP450 1A2 substrateNon-inhibitor0.8775
CYP450 2C9 inhibitorNon-inhibitor0.8541
CYP450 2D6 inhibitorNon-inhibitor0.8565
CYP450 2C19 inhibitorNon-inhibitor0.8465
CYP450 3A4 inhibitorNon-inhibitor0.9652
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.891
Ames testNon AMES toxic0.605
CarcinogenicityNon-carcinogens0.9077
BiodegradationNot ready biodegradable0.9162
Rat acute toxicity2.5342 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9522
hERG inhibition (predictor II)Non-inhibitor0.8244
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/MSsplash10-03di-0019000000-027a97e8ffca04733952
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-0497000000-116c415ff7b71db28b98
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0391000000-6411e8c4d4a2ffdc98a8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-2892000000-94690c2b13cba737ff66
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-5910000000-c58e73b121cd914845cc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-6920000000-6d96f35df2ca18dfde52
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]-178.39796
predicted
DeepCCS 1.0 (2019)
[M+H]+180.29338
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.15053
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glycogen phosphorylase, muscle form
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 at September 15, 2010 21:32 / Updated at June 12, 2020 16:52