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Hydroxy-Phenyl-Acetic Acid 8-Methyl-8-Aza-Bicyclo[3.2.1]Oct-3-Yl Ester

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Data Packages
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Identification

Generic Name
Hydroxy-Phenyl-Acetic Acid 8-Methyl-8-Aza-Bicyclo[3.2.1]Oct-3-Yl Ester
DrugBank Accession Number
DB02161
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 275.3428
Monoisotopic: 275.152143543
Chemical Formula
C16H21NO3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULiver carboxylesterase 1Not 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 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
Piperidines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkylamines / Secondary alcohols / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organic oxides
show 3 more
Substituents
Alcohol / Amine / Amino acid or derivatives / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 16 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
ZTVIKZXZYLEVOL-LXTVHRRPSA-N
InChI
InChI=1S/C16H21NO3/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13+,14-,15-/m1/s1
IUPAC Name
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2R)-2-hydroxy-2-phenylacetate
SMILES
[H][C@](O)(C(=O)O[C@@]1([H])C[C@]2([H])CC[C@]([H])(C1)N2C)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
447234
PubChem Substance
46506304
ZINC
ZINC000101317194
PDBe Ligand
HTQ
PDB Entries
1mx5 / 2dqz

Clinical Trials

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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 Solubility5.57 mg/mLALOGPS
logP1.91ALOGPS
logP1.59Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.99Chemaxon
pKa (Strongest Basic)9.38Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.77 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity75.81 m3·mol-1Chemaxon
Polarizability29.29 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.899
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8056
P-glycoprotein substrateSubstrate0.5336
P-glycoprotein inhibitor IInhibitor0.6116
P-glycoprotein inhibitor IINon-inhibitor0.961
Renal organic cation transporterInhibitor0.6806
CYP450 2C9 substrateNon-substrate0.699
CYP450 2D6 substrateNon-substrate0.6588
CYP450 3A4 substrateSubstrate0.6287
CYP450 1A2 substrateNon-inhibitor0.9179
CYP450 2C9 inhibitorNon-inhibitor0.9296
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9375
CYP450 3A4 inhibitorNon-inhibitor0.9702
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9564
Ames testNon AMES toxic0.7026
CarcinogenicityNon-carcinogens0.9711
BiodegradationNot ready biodegradable0.6278
Rat acute toxicity2.5928 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9392
hERG inhibition (predictor II)Non-inhibitor0.6657
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-MSsplash10-0a4i-1900000000-dd60d5b701d6363758b0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-33d57aeac00280f5f9dc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0970000000-7a9ba483aacb93e47583
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05di-0590000000-3c323792686ae6de5e15
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-2910000000-b6548a18e97680b6b011
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-7910000000-b6ad90e0bd24e787a855
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2910000000-36d582f1e6d2bc27fb78
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]-161.11572
predicted
DeepCCS 1.0 (2019)
[M+H]+163.51129
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.42381
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Liver carboxylesterase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
Specific Function
Carboxylesterase activity
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52