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Identification
Name3-[2-(2-BENZYLOXYCARBONYLAMINO-3-METHYL-BUTYRYLAMINO)-PROPIONYLAMINO]-4-OXO-PENTANOIC ACID
Accession NumberDB07744
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: 435.4709
Monoisotopic: 435.200550297
Chemical FormulaC21H29N3O7
InChI KeyCYBAOBDVBPVSDJ-OWQGQXMQSA-N
InChI
InChI=1S/C21H29N3O7/c1-12(2)18(24-21(30)31-11-15-8-6-5-7-9-15)20(29)22-13(3)19(28)23-16(14(4)25)10-17(26)27/h5-9,12-13,16,18H,10-11H2,1-4H3,(H,22,29)(H,23,28)(H,24,30)(H,26,27)/t13-,16-,18-/m0/s1
IUPAC Name
(3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-4-oxopentanoic acid
SMILES
[H][C@@](C)(NC(=O)[C@@]([H])(NC(=O)OCC1=CC=CC=C1)C(C)C)C(=O)N[C@@]([H])(CC(O)=O)C(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 Solubility0.0729 mg/mLALOGPS
logP1.02ALOGPS
logP1.09ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.9 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity109.35 m3·mol-1ChemAxon
Polarizability44.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7761
Blood Brain Barrier-0.7676
Caco-2 permeable-0.784
P-glycoprotein substrateSubstrate0.5932
P-glycoprotein inhibitor INon-inhibitor0.6455
P-glycoprotein inhibitor IINon-inhibitor0.9201
Renal organic cation transporterNon-inhibitor0.9549
CYP450 2C9 substrateNon-substrate0.7854
CYP450 2D6 substrateNon-substrate0.7948
CYP450 3A4 substrateNon-substrate0.5648
CYP450 1A2 substrateNon-inhibitor0.7601
CYP450 2C9 inhibitorNon-inhibitor0.8935
CYP450 2D6 inhibitorNon-inhibitor0.9282
CYP450 2C19 inhibitorNon-inhibitor0.6948
CYP450 3A4 inhibitorNon-inhibitor0.6306
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.913
Ames testNon AMES toxic0.8032
CarcinogenicityNon-carcinogens0.878
BiodegradationNot ready biodegradable0.7344
Rat acute toxicity2.2208 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.989
hERG inhibition (predictor II)Non-inhibitor0.9409
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 hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassPeptidomimetics
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Alpha-dipeptide
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Beta amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Benzyloxycarbonyl
  • Gamma-keto acid
  • Keto acid
  • Fatty amide
  • Benzenoid
  • Fatty acyl
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Carbamic acid ester
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 ]
Comments
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Drug created on September 15, 2010 15:25 / Updated on August 17, 2016 12:24