(1S,3R,6S)-4-oxo-6-{4-[(2-phenylquinolin-4-yl)methoxy]phenyl}-5-azaspiro[2.4]heptane-1-carboxylic acid

Identification

Name
(1S,3R,6S)-4-oxo-6-{4-[(2-phenylquinolin-4-yl)methoxy]phenyl}-5-azaspiro[2.4]heptane-1-carboxylic acid
Accession Number
DB07189
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: 464.5119
Monoisotopic: 464.173607266
Chemical Formula
C29H24N2O4
InChI Key
BFZXMIUWGSTUAL-ZSOKXDGFSA-N
InChI
InChI=1S/C29H24N2O4/c32-27(33)23-15-29(23)16-26(31-28(29)34)19-10-12-21(13-11-19)35-17-20-14-25(18-6-2-1-3-7-18)30-24-9-5-4-8-22(20)24/h1-14,23,26H,15-17H2,(H,31,34)(H,32,33)/t23-,26+,29-/m1/s1
IUPAC Name
(1S,3R,6S)-4-oxo-6-{4-[(2-phenylquinolin-4-yl)methoxy]phenyl}-5-azaspiro[2.4]heptane-1-carboxylic acid
SMILES
[H][[email protected]@]1(C[[email protected]@]11C[[email protected]]([H])(NC1=O)C1=CC=C(OCC2=CC(=NC3=C2C=CC=C3)C2=CC=CC=C2)C=C1)C(O)=O

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
25049750
PubChem Substance
99443660
ChemSpider
25056739
HET
642
PDB Entries
3ewj

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 Solubility0.000513 mg/mLALOGPS
logP4.59ALOGPS
logP4.3ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)3.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.82 m3·mol-1ChemAxon
Polarizability50.58 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9508
Blood Brain Barrier+0.8294
Caco-2 permeable-0.7845
P-glycoprotein substrateSubstrate0.637
P-glycoprotein inhibitor INon-inhibitor0.9585
P-glycoprotein inhibitor IINon-inhibitor0.7752
Renal organic cation transporterNon-inhibitor0.8173
CYP450 2C9 substrateNon-substrate0.8251
CYP450 2D6 substrateNon-substrate0.782
CYP450 3A4 substrateSubstrate0.5444
CYP450 1A2 substrateNon-inhibitor0.5303
CYP450 2C9 inhibitorNon-inhibitor0.602
CYP450 2D6 inhibitorNon-inhibitor0.7299
CYP450 2C19 inhibitorNon-inhibitor0.7582
CYP450 3A4 inhibitorNon-inhibitor0.5542
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6544
Ames testNon AMES toxic0.7919
CarcinogenicityNon-carcinogens0.9222
BiodegradationNot ready biodegradable0.9921
Rat acute toxicity2.6694 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9978
hERG inhibition (predictor II)Non-inhibitor0.7502
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 phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Phenylpyridines / Phenylpyrrolidines / Phenol ethers / Phenoxy compounds / Alkyl aryl ethers / Cyclopropanecarboxylic acids / Pyrrolidine-2-ones / Heteroaromatic compounds / Pyrroles / Lactams
show 9 more
Substituents
Phenylquinoline / 2-phenylpyridine / 2-phenylpyrrolidine / Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Cyclopropanecarboxylic acid / Cyclopropanecarboxylic acid or derivatives / Pyridine
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

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 15:47