3-{6-[(8-HYDROXY-QUINOLINE-2-CARBONYL)-AMINO]-2-THIOPHEN-2-YL-HEXANOYLAMINO}-4-OXO-BUTYRI ACID

Identification

Name
3-{6-[(8-HYDROXY-QUINOLINE-2-CARBONYL)-AMINO]-2-THIOPHEN-2-YL-HEXANOYLAMINO}-4-OXO-BUTYRI ACID
Accession Number
DB07916
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: 483.537
Monoisotopic: 483.146406237
Chemical Formula
C24H25N3O6S
InChI Key
QXMPYGCWDMKRMF-IRXDYDNUSA-N
InChI
InChI=1S/C24H25N3O6S/c28-14-16(13-21(30)31)26-23(32)17(20-8-4-12-34-20)6-1-2-11-25-24(33)18-10-9-15-5-3-7-19(29)22(15)27-18/h3-5,7-10,12,14,16-17,29H,1-2,6,11,13H2,(H,25,33)(H,26,32)(H,30,31)/t16-,17-/m0/s1
IUPAC Name
(3S)-3-[(2R)-6-[(8-hydroxyquinolin-2-yl)formamido]-2-(thiophen-2-yl)hexanamido]-4-oxobutanoic acid
SMILES
[H][[email protected]@](CC(O)=O)(NC(=O)[[email protected]@]([H])(CCCCNC(=O)C1=NC2=C(C=CC=C2O)C=C1)C1=CC=CS1)C=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCaspase-1Not 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
5288581
PubChem Substance
99444387
ChemSpider
4450715
HET
HQC
PDB Entries
1rwp

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 Solubility0.00418 mg/mLALOGPS
logP2.39ALOGPS
logP2.43ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)0.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.69 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity124.27 m3·mol-1ChemAxon
Polarizability49.96 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7954
Blood Brain Barrier-0.7288
Caco-2 permeable-0.8534
P-glycoprotein substrateSubstrate0.7074
P-glycoprotein inhibitor INon-inhibitor0.9629
P-glycoprotein inhibitor IINon-inhibitor0.9208
Renal organic cation transporterNon-inhibitor0.7899
CYP450 2C9 substrateNon-substrate0.7459
CYP450 2D6 substrateNon-substrate0.7647
CYP450 3A4 substrateNon-substrate0.5459
CYP450 1A2 substrateNon-inhibitor0.7274
CYP450 2C9 inhibitorNon-inhibitor0.6353
CYP450 2D6 inhibitorNon-inhibitor0.8082
CYP450 2C19 inhibitorNon-inhibitor0.7487
CYP450 3A4 inhibitorNon-inhibitor0.9196
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5071
Ames testNon AMES toxic0.7847
CarcinogenicityNon-carcinogens0.9494
BiodegradationNot ready biodegradable0.9511
Rat acute toxicity2.2163 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9738
hERG inhibition (predictor II)Non-inhibitor0.5595
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 quinoline carboxamides. These are quinolines in which the quinoline ring system is substituted by one or more carboxamide groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxamides
Direct Parent
Quinoline carboxamides
Alternative Parents
Hydroxyquinolines / 8-hydroxyquinolines / Beta amino acids and derivatives / Pyridinecarboxylic acids and derivatives / 2-heteroaryl carboxamides / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / N-acyl amines / Thiophenes / Heteroaromatic compounds
show 9 more
Substituents
Quinoline-2-carboxamide / Beta amino acid or derivatives / Hydroxyquinoline / 8-hydroxyquinoline / Pyridine carboxylic acid or derivatives / 2-heteroaryl carboxamide / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Fatty amide / N-acyl-amine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Endopeptidase activity
Specific Function
Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cle...
Gene Name
CASP1
Uniprot ID
P29466
Uniprot Name
Caspase-1
Molecular Weight
45158.215 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 15:27 / Updated on December 01, 2017 15:57