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Identification
Name(2s,4r)-1-Acetyl-N-[(1s)-4-[(Aminoiminomethyl)Amino]-1-(2-Benzothiazolylcarbonyl)Butyl]-4-Hydroxy-2-Pyrrolidinecarboxamide
Accession NumberDB02812  (EXPT00391)
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: 446.523
Monoisotopic: 446.17362404
Chemical FormulaC20H26N6O4S
InChI KeyInChIKey=VXDAVYUFYPFGDX-CFVMTHIKSA-N
InChI
InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15-/m0/s1
IUPAC Name
(2S,4S)-1-acetyl-N-[(2R)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
SMILES
CC(=O)N1C[C@@H](O)C[[email protected]]1C(=O)N[[email protected]](CCCNC(N)=N)C(=O)C1=NC2=C(S1)C=CC=C2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 1,3-benzothiazole
  • Aryl alkyl ketone
  • Aryl ketone
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Benzenoid
  • Heteroaromatic compound
  • Acetamide
  • Thiazole
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Azole
  • Alpha-aminoketone
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Alcohol
  • 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+0.9003
Blood Brain Barrier-0.886
Caco-2 permeable-0.804
P-glycoprotein substrateSubstrate0.8239
P-glycoprotein inhibitor INon-inhibitor0.9212
P-glycoprotein inhibitor IINon-inhibitor0.8726
Renal organic cation transporterNon-inhibitor0.6401
CYP450 2C9 substrateNon-substrate0.702
CYP450 2D6 substrateNon-substrate0.7862
CYP450 3A4 substrateNon-substrate0.54
CYP450 1A2 substrateNon-inhibitor0.7214
CYP450 2C9 inhibitorNon-inhibitor0.7349
CYP450 2D6 inhibitorNon-inhibitor0.888
CYP450 2C19 inhibitorNon-inhibitor0.6851
CYP450 3A4 inhibitorNon-inhibitor0.6974
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7459
Ames testNon AMES toxic0.6824
CarcinogenicityNon-carcinogens0.8778
BiodegradationNot ready biodegradable0.9723
Rat acute toxicity2.5098 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9665
hERG inhibition (predictor II)Non-inhibitor0.6539
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 Solubility0.134 mg/mLALOGPS
logP0.1ALOGPS
logP-1.1ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)11.72ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.5 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.04 m3·mol-1ChemAxon
Polarizability46.65 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 Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Serine-type endopeptidase activity
Specific Function:
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates.
Gene Name:
PRSS1
Uniprot ID:
P07477
Molecular Weight:
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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 June 13, 2005 07:24 / Updated on September 16, 2013 17:19