(2s,4r)-1-Acetyl-N-[(1s)-4-[(Aminoiminomethyl)Amino]-1-(2-Benzothiazolylcarbonyl)Butyl]-4-Hydroxy-2-Pyrrolidinecarboxamide

Identification

Name
(2s,4r)-1-Acetyl-N-[(1s)-4-[(Aminoiminomethyl)Amino]-1-(2-Benzothiazolylcarbonyl)Butyl]-4-Hydroxy-2-Pyrrolidinecarboxamide
Accession Number
DB02812  (EXPT00391)
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: 446.523
Monoisotopic: 446.17362404
Chemical Formula
C20H26N6O4S
InChI Key
VXDAVYUFYPFGDX-SNPRPXQTSA-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+/m1/s1
IUPAC Name
(2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboximidic acid
SMILES
[H][[email protected]@](CCCNC(N)=N)(N=C(O)[[email protected]]1([H])C[[email protected]@]([H])(O)CN1C(C)=O)C(=O)C1=NC2=CC=CC=C2S1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-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
5287596
PubChem Substance
46509114
ChemSpider
4449928
BindingDB
50228764
ChEMBL
CHEMBL256892
HET
ABB
PDB Entries
1nc6

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 Solubility0.14 mg/mLALOGPS
logP0.17ALOGPS
logP-1.6ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)5.89ChemAxon
pKa (Strongest Basic)11.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.99 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.56 m3·mol-1ChemAxon
Polarizability46.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Benzothiazoles / Aryl alkyl ketones / N-acylpyrrolidines / Pyrrolidinecarboxamides / Benzenoids / Heteroaromatic compounds / Acetamides / Tertiary carboxylic acid amides / Thiazoles
show 8 more
Substituents
Proline or derivatives / Alpha-amino acid amide / 1,3-benzothiazole / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Aryl alkyl ketone / Aryl ketone / Benzenoid / Azole
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, guanidines, pyrrolidinecarboxamide, L-proline derivative, N-acylpyrrolidine (CHEBI:40491)

Targets

Details
1. Trypsin-1
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 aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:03