methyl (1R,2S)-2-(hydroxycarbamoyl)-1-{4-[(2-methylquinolin-4-yl)methoxy]benzyl}cyclopropanecarboxylate

Identification

Name
methyl (1R,2S)-2-(hydroxycarbamoyl)-1-{4-[(2-methylquinolin-4-yl)methoxy]benzyl}cyclopropanecarboxylate
Accession Number
DB07147
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: 420.4578
Monoisotopic: 420.168521888
Chemical Formula
C24H24N2O5
InChI Key
HJWMYFBKJRVWJY-YKSBVNFPSA-N
InChI
InChI=1S/C24H24N2O5/c1-15-11-17(19-5-3-4-6-21(19)25-15)14-31-18-9-7-16(8-10-18)12-24(23(28)30-2)13-20(24)22(27)26-29/h3-11,20,29H,12-14H2,1-2H3,(H,26,27)/t20-,24+/m1/s1
IUPAC Name
methyl (1R,2S)-2-(hydroxycarbamoyl)-1-({4-[(2-methylquinolin-4-yl)methoxy]phenyl}methyl)cyclopropane-1-carboxylate
SMILES
[H][[email protected]@]1(C[[email protected]]1(CC1=CC=C(OCC2=CC(C)=NC3=C2C=CC=C3)C=C1)C(=O)OC)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
24800833
PubChem Substance
99443618
ChemSpider
23325936
BindingDB
23484
ChEMBL
CHEMBL410462
HET
550
PDB Entries
3edz

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 Solubility0.0023 mg/mLALOGPS
logP3.81ALOGPS
logP3.11ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.75 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.42 m3·mol-1ChemAxon
Polarizability44.95 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7354
Blood Brain Barrier+0.6867
Caco-2 permeable-0.6604
P-glycoprotein substrateSubstrate0.6224
P-glycoprotein inhibitor INon-inhibitor0.8375
P-glycoprotein inhibitor IINon-inhibitor0.7036
Renal organic cation transporterNon-inhibitor0.8911
CYP450 2C9 substrateNon-substrate0.8567
CYP450 2D6 substrateNon-substrate0.8119
CYP450 3A4 substrateSubstrate0.6691
CYP450 1A2 substrateNon-inhibitor0.5921
CYP450 2C9 inhibitorNon-inhibitor0.5632
CYP450 2D6 inhibitorNon-inhibitor0.8399
CYP450 2C19 inhibitorNon-inhibitor0.6476
CYP450 3A4 inhibitorNon-inhibitor0.5487
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6316
Ames testAMES toxic0.528
CarcinogenicityNon-carcinogens0.8765
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7595 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.6053
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 quinolines and derivatives. These are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Not Available
Direct Parent
Quinolines and derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Fatty acid esters / Methylpyridines / Cyclopropanecarboxylic acids and derivatives / Heteroaromatic compounds / Methyl esters / Hydroxamic acids / Azacyclic compounds
show 6 more
Substituents
Quinoline / Phenoxy compound / Phenol ether / Alkyl aryl ether / Methylpyridine / Fatty acid ester / Monocyclic benzene moiety / Cyclopropanecarboxylic acid or derivatives / Fatty acyl / Benzenoid
show 18 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 15:46