(R)-(+) 5(9BH)-OXO-9B-PHENYL-2,3-DIHYDROTHIAZOLO[2,3-A]ISOINDOL-3-CARBOXYLIC ACID METHYL ESTER

Identification

Name
(R)-(+) 5(9BH)-OXO-9B-PHENYL-2,3-DIHYDROTHIAZOLO[2,3-A]ISOINDOL-3-CARBOXYLIC ACID METHYL ESTER
Accession Number
DB07473
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: 325.382
Monoisotopic: 325.077264041
Chemical Formula
C18H15NO3S
InChI Key
JYIHODAXBBPFQF-MAUKXSAKSA-N
InChI
InChI=1S/C18H15NO3S/c1-22-17(21)15-11-23-18(12-7-3-2-4-8-12)14-10-6-5-9-13(14)16(20)19(15)18/h2-10,15H,11H2,1H3/t15-,18+/m0/s1
IUPAC Name
methyl (3R,9bR)-5-oxo-9b-phenyl-2H,3H,5H,9bH-[1,3]thiazolo[2,3-a]isoindole-3-carboxylate
SMILES
COC(=O)[[email protected]@H]1CS[[email protected]]2(N1C(=O)C1=CC=CC=C21)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot AvailableHIV-1
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
444704
PubChem Substance
99443944
ChemSpider
392561
HET
BM5
PDB Entries
1c0u

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 Solubility0.0147 mg/mLALOGPS
logP2.93ALOGPS
logP3.45ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.85 m3·mol-1ChemAxon
Polarizability33.31 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9843
Blood Brain Barrier+0.9105
Caco-2 permeable+0.5668
P-glycoprotein substrateNon-substrate0.6467
P-glycoprotein inhibitor INon-inhibitor0.8867
P-glycoprotein inhibitor IINon-inhibitor0.853
Renal organic cation transporterNon-inhibitor0.7822
CYP450 2C9 substrateNon-substrate0.6948
CYP450 2D6 substrateNon-substrate0.7853
CYP450 3A4 substrateSubstrate0.599
CYP450 1A2 substrateInhibitor0.5805
CYP450 2C9 inhibitorInhibitor0.7004
CYP450 2D6 inhibitorNon-inhibitor0.8683
CYP450 2C19 inhibitorInhibitor0.7532
CYP450 3A4 inhibitorNon-inhibitor0.5084
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.652
Ames testNon AMES toxic0.6323
CarcinogenicityNon-carcinogens0.897
BiodegradationNot ready biodegradable0.9662
Rat acute toxicity2.4447 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.8241
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 alpha amino acid esters. These are ester derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid esters
Alternative Parents
Isoindolones / Isoindoles / Benzene and substituted derivatives / Thiazolidines / Tertiary carboxylic acid amides / Methyl esters / Lactams / Monocarboxylic acids and derivatives / Dialkylthioethers / Azacyclic compounds
show 5 more
Substituents
Alpha-amino acid ester / Isoindolone / Isoindoline / Isoindole / Isoindole or derivatives / Monocyclic benzene moiety / Benzenoid / Methyl ester / Thiazolidine / Tertiary carboxylic acid amide
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
methyl ester, thiazoloisoindole (CHEBI:41211)

Targets

Kind
Protein
Organism
HIV-1
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P04585
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
162041.05 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 15:22 / Updated on December 01, 2017 15:51