3-(HYDROXY-PHENYL-PHOSPHINOYLOXY)-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID METHYL ESTER

Identification

Generic Name
3-(HYDROXY-PHENYL-PHOSPHINOYLOXY)-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID METHYL ESTER
DrugBank Accession Number
DB08618
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 339.3233
Monoisotopic: 339.123559331
Chemical Formula
C16H22NO5P
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
UIg gamma-2 chain C regionNot 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 tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Not Available
Direct Parent
Tropane alkaloids
Alternative Parents
Piperidinecarboxylic acids / Phosphonic acid esters / N-alkylpyrrolidines / Benzene and substituted derivatives / Organic phosphonic acids / Methyl esters / Trialkylamines / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds
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Substituents
Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Methyl ester
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tropane alkaloid, phosphonic ester, methyl ester (CHEBI:273574)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
WJTKWTJTOSZMKO-PMOUVXMZSA-N
InChI
InChI=1S/C16H22NO5P/c1-17-11-8-9-13(17)15(16(18)21-2)14(10-11)22-23(19,20)12-6-4-3-5-7-12/h3-7,11,13-15H,8-10H2,1-2H3,(H,19,20)/t11-,13+,14-,15+/m0/s1
IUPAC Name
{[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]oxy}(phenyl)phosphinic acid
SMILES
[H][C@@]12CC[C@@]([H])(N1C)[C@@]([H])(C(=O)OC)[C@]([H])(C2)O[P@](O)(=O)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
644013
PubChem Substance
99445089
ChemSpider
559089
ChEBI
273574
ZINC
ZINC000016051773
PDBe Ligand
TGN
PDB Entries
2ajx

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 Solubility9.49 mg/mLALOGPS
logP0.91ALOGPS
logP-0.33ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.12ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.81 m3·mol-1ChemAxon
Polarizability33.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.901
Blood Brain Barrier+0.8488
Caco-2 permeable+0.5103
P-glycoprotein substrateNon-substrate0.5114
P-glycoprotein inhibitor IInhibitor0.6206
P-glycoprotein inhibitor IINon-inhibitor0.9837
Renal organic cation transporterNon-inhibitor0.5605
CYP450 2C9 substrateNon-substrate0.71
CYP450 2D6 substrateNon-substrate0.8531
CYP450 3A4 substrateSubstrate0.6785
CYP450 1A2 substrateNon-inhibitor0.8381
CYP450 2C9 inhibitorNon-inhibitor0.868
CYP450 2D6 inhibitorNon-inhibitor0.8575
CYP450 2C19 inhibitorNon-inhibitor0.8519
CYP450 3A4 inhibitorNon-inhibitor0.9236
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9733
Ames testNon AMES toxic0.6344
CarcinogenicityNon-carcinogens0.9135
BiodegradationNot ready biodegradable0.6613
Rat acute toxicity3.0262 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6681
hERG inhibition (predictor II)Non-inhibitor0.7276
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
Humans
Pharmacological action
Unknown
General Function
Immunoglobulin receptor binding
Specific Function
Not Available
Gene Name
IGHG2
Uniprot ID
P01859
Uniprot Name
Ig gamma-2 chain C region
Molecular Weight
35900.445 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 21:33 / Updated at June 12, 2020 16:52