(2R)-N-HYDROXY-2-[(3S)-3-METHYL-3-{4-[(2-METHYLQUINOLIN-4-YL)METHOXY]PHENYL}-2-OXOPYRROLIDIN-1-YL]PROPANAMIDE

Identification

Name
(2R)-N-HYDROXY-2-[(3S)-3-METHYL-3-{4-[(2-METHYLQUINOLIN-4-YL)METHOXY]PHENYL}-2-OXOPYRROLIDIN-1-YL]PROPANAMIDE
Accession Number
DB07145
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: 433.4996
Monoisotopic: 433.200156367
Chemical Formula
C25H27N3O4
InChI Key
YDMIPBHQKFOFQW-NSYGIPOTSA-N
InChI
InChI=1S/C25H27N3O4/c1-16-14-18(21-6-4-5-7-22(21)26-16)15-32-20-10-8-19(9-11-20)25(3)12-13-28(24(25)30)17(2)23(29)27-31/h4-11,14,17,31H,12-13,15H2,1-3H3,(H,27,29)/t17-,25+/m1/s1
IUPAC Name
(2R)-N-hydroxy-2-[(3S)-3-methyl-3-{4-[(2-methylquinolin-4-yl)methoxy]phenyl}-2-oxopyrrolidin-1-yl]propanamide
SMILES
[H][[email protected]](C)(N1CC[[email protected]](C)(C1=O)C1=CC=C(OCC2=CC(C)=NC3=CC=CC=C23)C=C1)C(=O)NO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDisintegrin and metalloproteinase domain-containing protein 17Not AvailableHuman
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
6914621
PubChem Substance
99443616
ChemSpider
5290501
BindingDB
26526
ChEBI
40083
ChEMBL
CHEMBL148169
HET
541
PDB Entries
2fv5

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 Solubility0.00414 mg/mLALOGPS
logP3.8ALOGPS
logP2.97ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.76 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.08 m3·mol-1ChemAxon
Polarizability47.66 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9653
Blood Brain Barrier-0.7125
Caco-2 permeable-0.7048
P-glycoprotein substrateSubstrate0.7943
P-glycoprotein inhibitor INon-inhibitor0.5687
P-glycoprotein inhibitor IIInhibitor0.9517
Renal organic cation transporterNon-inhibitor0.7767
CYP450 2C9 substrateNon-substrate0.8137
CYP450 2D6 substrateNon-substrate0.7759
CYP450 3A4 substrateSubstrate0.7324
CYP450 1A2 substrateNon-inhibitor0.8444
CYP450 2C9 inhibitorInhibitor0.5546
CYP450 2D6 inhibitorNon-inhibitor0.7629
CYP450 2C19 inhibitorNon-inhibitor0.5161
CYP450 3A4 inhibitorInhibitor0.7827
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7073
Ames testNon AMES toxic0.5656
CarcinogenicityNon-carcinogens0.7714
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6764 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9785
hERG inhibition (predictor II)Inhibitor0.5432
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/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 phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. 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
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Quinolines and derivatives / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Methylpyridines / Pyrrolidine-2-ones / N-alkylpyrrolidines / Tertiary carboxylic acid amides / Pyrroles / Heteroaromatic compounds
show 7 more
Substituents
3-phenylpyrrolidine / Quinoline / Phenoxy compound / Phenol ether / Alkyl aryl ether / Methylpyridine / Monocyclic benzene moiety / Pyridine / Pyrrolidone / 2-pyrrolidone
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, hydroxamic acid, pyrrolidin-2-ones (CHEBI:40083)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Cleaves the membrane-bound precursor of TNF-alpha to its mature soluble form. Responsible for the proteolytical release of soluble JAM3 from endothelial cells surface. Responsible for the proteolyt...
Gene Name
ADAM17
Uniprot ID
P78536
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 17
Molecular Weight
93020.165 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 15:19 / Updated on December 01, 2017 15:46