(2R)-2-(5-CHLORO-2-THIENYL)-N-{(3S)-1-[(1S)-1-METHYL-2-MORPHOLIN-4-YL-2-OXOETHYL]-2-OXOPYRROLIDIN-3-YL}PROPENE-1-SULFONAMIDE

Identification

Name
(2R)-2-(5-CHLORO-2-THIENYL)-N-{(3S)-1-[(1S)-1-METHYL-2-MORPHOLIN-4-YL-2-OXOETHYL]-2-OXOPYRROLIDIN-3-YL}PROPENE-1-SULFONAMIDE
Accession Number
DB07211
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: 461.983
Monoisotopic: 461.08458998
Chemical Formula
C18H24ClN3O5S2
InChI Key
YMJHMJLNQLVUAV-GHYUOPHCSA-N
InChI
InChI=1S/C18H24ClN3O5S2/c1-12(15-3-4-16(19)28-15)11-29(25,26)20-14-5-6-22(18(14)24)13(2)17(23)21-7-9-27-10-8-21/h3-4,11,13-14,20H,5-10H2,1-2H3/b12-11+/t13-,14-/m0/s1
IUPAC Name
(1E)-2-(5-chlorothiophen-2-yl)-N-[(3S)-1-[(2S)-1-(morpholin-4-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]prop-1-ene-1-sulfonamide
SMILES
C\C(=C/S(=O)(=O)N[[email protected]@]1([H])CCN([[email protected]](C)([H])C(=O)N2CCOCC2)C1=O)C1=CC=C(Cl)S1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProthrombinNot AvailableHuman
UCoagulation factor XNot 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
10095865
PubChem Substance
99443682
ChemSpider
8271400
BindingDB
50206984
ChEMBL
CHEMBL391640
HET
701
PDB Entries
2jh0 / 2uwo

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 Solubility0.0804 mg/mLALOGPS
logP0.87ALOGPS
logP0.69ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.02 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.64 m3·mol-1ChemAxon
Polarizability46.39 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.5724
Caco-2 permeable-0.651
P-glycoprotein substrateSubstrate0.777
P-glycoprotein inhibitor IInhibitor0.646
P-glycoprotein inhibitor IINon-inhibitor0.991
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.721
CYP450 2D6 substrateNon-substrate0.7988
CYP450 3A4 substrateSubstrate0.6382
CYP450 1A2 substrateNon-inhibitor0.7746
CYP450 2C9 inhibitorNon-inhibitor0.6612
CYP450 2D6 inhibitorNon-inhibitor0.8546
CYP450 2C19 inhibitorNon-inhibitor0.5261
CYP450 3A4 inhibitorNon-inhibitor0.7863
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7427
Ames testNon AMES toxic0.5731
CarcinogenicityNon-carcinogens0.7796
BiodegradationNot ready biodegradable0.6926
Rat acute toxicity2.6182 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7181
hERG inhibition (predictor II)Non-inhibitor0.6334
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acids and derivatives / 2,5-disubstituted thiophenes / Pyrrolidine-2-ones / Organosulfonamides / Organic sulfonamides / Aryl chlorides / N-alkylpyrrolidines / Morpholines / Tertiary carboxylic acid amides / Aminosulfonyl compounds
show 11 more
Substituents
Alpha-dipeptide / Alpha-amino acid or derivatives / 2,5-disubstituted thiophene / Aryl chloride / Aryl halide / Morpholine / Oxazinane / Pyrrolidone / 2-pyrrolidone / Organic sulfonic acid amide
show 29 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, organochlorine compound, thiophenes, morpholines, pyrrolidin-2-ones (CHEBI:47161)

Targets

Details
1. Prothrombin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thrombospondin receptor activity
Specific Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 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]
Details
2. Coagulation factor X
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name
F10
Uniprot ID
P00742
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 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 15:19 / Updated on December 01, 2017 15:47