Nalpha-(2-Naphthylsulfonylglycyl)-3-Amidino-D,L-Phenylalanine-Isopropylester

Identification

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Name
Nalpha-(2-Naphthylsulfonylglycyl)-3-Amidino-D,L-Phenylalanine-Isopropylester
Accession Number
DB01737  (EXPT00521)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
133397-81-6
Weight
Average: 432.493
Monoisotopic: 432.146740588
Chemical Formula
C20H24N4O5S
InChI Key
YAEIKQDHLCFGAA-KRWDZBQOSA-N
InChI
InChI=1S/C20H24N4O5S/c1-13-6-8-16(9-7-13)30(27,28)23-12-18(25)24-17(20(26)29-2)11-14-4-3-5-15(10-14)19(21)22/h3-10,17,23H,11-12H2,1-2H3,(H3,21,22)(H,24,25)/t17-/m0/s1
IUPAC Name
methyl (2S)-3-(3-carbamimidoylphenyl)-2-[2-(4-methylbenzenesulfonamido)acetamido]propanoate
SMILES
[H][C@@](CC1=CC=CC(=C1)C(N)=N)(NC(=O)CNS(=O)(=O)C1=CC=C(C)C=C1)C(=O)OC

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-1Not AvailableHumans
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
131624
PubChem Substance
46505569
ChemSpider
116313
HET
ANH
PDB Entries
1v2o / 1v2p / 1v2q / 1v2r / 1v2t / 1v2w / 3plk / 3pwc / 3uns / 3uwi
show 1 more

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 Solubility0.0392 mg/mLALOGPS
logP0.43ALOGPS
logP0.54ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)11.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area151.44 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity122.6 m3·mol-1ChemAxon
Polarizability44.45 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7925
Blood Brain Barrier+0.6527
Caco-2 permeable-0.6944
P-glycoprotein substrateSubstrate0.5305
P-glycoprotein inhibitor INon-inhibitor0.8244
P-glycoprotein inhibitor IINon-inhibitor0.8745
Renal organic cation transporterNon-inhibitor0.8348
CYP450 2C9 substrateNon-substrate0.6362
CYP450 2D6 substrateNon-substrate0.819
CYP450 3A4 substrateNon-substrate0.6031
CYP450 1A2 substrateNon-inhibitor0.885
CYP450 2C9 inhibitorNon-inhibitor0.6659
CYP450 2D6 inhibitorNon-inhibitor0.9048
CYP450 2C19 inhibitorNon-inhibitor0.5872
CYP450 3A4 inhibitorNon-inhibitor0.6538
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7455
Ames testNon AMES toxic0.6495
CarcinogenicityNon-carcinogens0.6726
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity2.5778 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9931
hERG inhibition (predictor II)Non-inhibitor0.8471
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 peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Phenylalanine and derivatives / Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / P-toluenesulfonamides / Amphetamines and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Fatty acid esters / Organosulfonamides
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Substituents
Alpha peptide / Phenylalanine or derivatives / Alpha-amino acid ester / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / P-toluenesulfonamide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Amphetamine or derivatives / Benzenesulfonamide
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
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. 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 August 02, 2019 06:54