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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 Identifiers 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
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 483.537
Monoisotopic: 483.146406237
Chemical FormulaC24H25N3O6S
InChI KeyInChIKey=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][C@@](CC(O)=O)(NC(=O)[C@@]([H])(CCCCNC(=O)C1=NC2=C(C=CC=C2O)C=C1)C1=CC=CS1)C=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxamides
Direct ParentQuinoline carboxamides
Alternative Parents
Substituents
  • Quinoline-2-carboxamide
  • 8-hydroxyquinoline
  • Hydroxyquinoline
  • Beta amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Pyridine
  • N-acyl-amine
  • Fatty amide
  • Heteroaromatic compound
  • Thiophene
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 ]
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Drug created on September 15, 2010 15:27 / Updated on September 16, 2013 18:07