Identification
Name3-{6-[(8-HYDROXY-QUINOLINE-2-CARBONYL)-AMINO]-2-THIOPHEN-2-YL-HEXANOYLAMINO}-4-OXO-BUTYRI ACID
Accession NumberDB07916
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 483.537
Monoisotopic: 483.146406237
Chemical FormulaC24H25N3O6S
InChI KeyQXMPYGCWDMKRMF-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][C@@](CC(O)=O)(NC(=O)[C@@]([H])(CCCCNC(=O)C1=NC2=C(C=CC=C2O)C=C1)C1=CC=CS1)C=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Caspase-1ProteinunknownNot AvailableHumanP29466 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as quinoline carboxamides. These are quinolines in which the quinoline ring system is substituted by one or more carboxamide groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct ParentQuinoline carboxamides
Alternative ParentsHydroxyquinolines / 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
SubstituentsQuinoline-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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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. Cleaves and activates sterol regulatory element binding proteins (SREBPs). Can also promote apoptosis.
Gene Name:
CASP1
Uniprot ID:
P29466
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 June 11, 2017 21:12