methyl (1R,2S)-2-(hydroxycarbamoyl)-1-{4-[(2-methylquinolin-4-yl)methoxy]benzyl}cyclopropanecarboxylate
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Identification
- Generic Name
- methyl (1R,2S)-2-(hydroxycarbamoyl)-1-{4-[(2-methylquinolin-4-yl)methoxy]benzyl}cyclopropanecarboxylate
- DrugBank Accession Number
- DB07147
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 420.4578
Monoisotopic: 420.168521888 - Chemical Formula
- C24H24N2O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDisintegrin and metalloproteinase domain-containing protein 17 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclopropanecarboxylic acid or derivatives / Ether / Fatty acid ester show 18 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
- 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][C@@]1(C[C@]1(CC1=CC=C(OCC2=CC(C)=NC3=C2C=CC=C3)C=C1)C(=O)OC)C(=O)NO
References
- General References
- Not Available
- External Links
- PubChem Compound
- 24800833
- PubChem Substance
- 99443618
- ChemSpider
- 23325936
- BindingDB
- 23484
- ChEMBL
- CHEMBL410462
- ZINC
- ZINC000029135377
- PDBe Ligand
- 550
- PDB Entries
- 3edz
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.0023 mg/mL ALOGPS logP 3.81 ALOGPS logP 3.11 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 8.86 Chemaxon pKa (Strongest Basic) 5.02 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 97.75 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 113.42 m3·mol-1 Chemaxon Polarizability 44.95 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7354 Blood Brain Barrier + 0.6867 Caco-2 permeable - 0.6604 P-glycoprotein substrate Substrate 0.6224 P-glycoprotein inhibitor I Non-inhibitor 0.8375 P-glycoprotein inhibitor II Non-inhibitor 0.7036 Renal organic cation transporter Non-inhibitor 0.8911 CYP450 2C9 substrate Non-substrate 0.8567 CYP450 2D6 substrate Non-substrate 0.8119 CYP450 3A4 substrate Substrate 0.6691 CYP450 1A2 substrate Non-inhibitor 0.5921 CYP450 2C9 inhibitor Non-inhibitor 0.5632 CYP450 2D6 inhibitor Non-inhibitor 0.8399 CYP450 2C19 inhibitor Non-inhibitor 0.6476 CYP450 3A4 inhibitor Non-inhibitor 0.5487 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6316 Ames test AMES toxic 0.528 Carcinogenicity Non-carcinogens 0.8765 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7595 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9968 hERG inhibition (predictor II) Non-inhibitor 0.6053
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-0905200000-8f836e9946254b570353 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fbi-0009100000-a617c2a82684f213e04c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-1109400000-fbc8cd8bda54e200a8f7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002f-1309000000-05952a79a8da3b47a43f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0910000000-0ef5cc07ebed006556ef Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-7609000000-4788c3cb29ca7c49c499 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.68944 predictedDeepCCS 1.0 (2019) [M+H]+ 189.08499 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.09538 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane metalloprotease which mediates the ectodomain shedding of a myriad of transmembrane proteins including adhesion proteins, growth factor precursors and cytokines important for inflammation and immunity (PubMed:24226769, PubMed:24227843, PubMed:28060820, PubMed:28923481). Cleaves the membrane-bound precursor of TNF-alpha to its mature soluble form (PubMed:9034191, PubMed:36078095). Responsible for the proteolytical release of soluble JAM3 from endothelial cells surface (PubMed:20592283). Responsible for the proteolytic release of several other cell-surface proteins, including p75 TNF-receptor, interleukin 1 receptor type II, p55 TNF-receptor, transforming growth factor-alpha, L-selectin, growth hormone receptor, MUC1 and the amyloid precursor protein (PubMed:12441351). Acts as an activator of Notch pathway by mediating cleavage of Notch, generating the membrane-associated intermediate fragment called Notch extracellular truncation (NEXT) (PubMed:24226769). Plays a role in the proteolytic processing of ACE2 (PubMed:24227843). Plays a role in hemostasis through shedding of GP1BA, the platelet glycoprotein Ib alpha chain (By similarity). Mediates the proteolytic cleavage of LAG3, leading to release the secreted form of LAG3 (By similarity). Mediates the proteolytic cleavage of IL6R, leading to the release of secreted form of IL6R (PubMed:26876177, PubMed:28060820). Mediates the proteolytic cleavage and shedding of FCGR3A upon NK cell stimulation, a mechanism that allows for increased NK cell motility and detachment from opsonized target cells. Cleaves TREM2, resulting in shedding of the TREM2 ectodomain (PubMed:28923481)
- Specific Function
- cytokine binding
- Gene Name
- ADAM17
- Uniprot ID
- P78536
- Uniprot Name
- Disintegrin and metalloproteinase domain-containing protein 17
- Molecular Weight
- 93020.165 Da
References
- 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