(6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one

Identification

Generic Name
(6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one
DrugBank Accession Number
DB07148
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 389.808
Monoisotopic: 389.094247337
Chemical Formula
C19H17ClFN3O3
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProlyl endopeptidaseNot 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 n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
N-acylpyrrolidines
Direct Parent
N-acylpyrrolidines
Alternative Parents
Alkyl aryl ethers / Fluorobenzenes / Pyrazines / Aryl chlorides / Aryl fluorides / Tertiary carboxylic acid amides / Heteroaromatic compounds / Lactams / Azacyclic compounds / Hydrocarbon derivatives
show 6 more
Substituents
Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 19 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
HPAFVLDARQIHPU-HNNXBMFYSA-N
InChI
InChI=1S/C19H17ClFN3O3/c20-16-14-7-8-15(18(25)23-9-1-2-10-23)24(14)19(26)17(22-16)27-11-12-3-5-13(21)6-4-12/h3-8,15H,1-2,9-11H2/t15-/m0/s1
IUPAC Name
(6S)-1-chloro-3-[(4-fluorophenyl)methoxy]-6-(pyrrolidine-1-carbonyl)-4H,6H-pyrrolo[1,2-a]pyrazin-4-one
SMILES
[H][C@]1(C=CC2=C(Cl)N=C(OCC3=CC=C(F)C=C3)C(=O)N12)C(=O)N1CCCC1

References

General References
Not Available
PubChem Compound
46937054
PubChem Substance
99443619
ChemSpider
25057581
ZINC
ZINC000039125249
PDBe Ligand
552
PDB Entries
3ddu

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 Solubility0.0289 mg/mLALOGPS
logP2.66ALOGPS
logP2.39Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)11.04Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area62.21 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity109.54 m3·mol-1Chemaxon
Polarizability37.22 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9821
Caco-2 permeable-0.5285
P-glycoprotein substrateSubstrate0.7299
P-glycoprotein inhibitor IInhibitor0.8001
P-glycoprotein inhibitor IIInhibitor0.8723
Renal organic cation transporterInhibitor0.5198
CYP450 2C9 substrateNon-substrate0.8208
CYP450 2D6 substrateNon-substrate0.7276
CYP450 3A4 substrateSubstrate0.6264
CYP450 1A2 substrateInhibitor0.6004
CYP450 2C9 inhibitorNon-inhibitor0.5483
CYP450 2D6 inhibitorNon-inhibitor0.8515
CYP450 2C19 inhibitorInhibitor0.6315
CYP450 3A4 inhibitorNon-inhibitor0.5698
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9241
Ames testNon AMES toxic0.7313
CarcinogenicityNon-carcinogens0.9337
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3563 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8578
hERG inhibition (predictor II)Inhibitor0.8051
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/MSsplash10-0006-0209000000-439cad5a2e26023809e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000b-9016000000-e83d915357614e4500b3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1019000000-83f82d7fd932f4c4672a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5d-5915000000-26a512045ed80b3879ac
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xu-2791000000-b4b0cdb79e619d8a23eb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-9717000000-af85a31f6f6d2e800aa6
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]-190.07812
predicted
DeepCCS 1.0 (2019)
[M+H]+192.43614
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.04231
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long.
Gene Name
PREP
Uniprot ID
P48147
Uniprot Name
Prolyl endopeptidase
Molecular Weight
80698.945 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 21:19 / Updated at June 12, 2020 16:52