N-Alpha-(2-Naphthylsulfonyl)-N(3-Amidino-L-Phenylalaninyl)Isopipecolinic Acid Methyl Ester

Identification

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Name
N-Alpha-(2-Naphthylsulfonyl)-N(3-Amidino-L-Phenylalaninyl)Isopipecolinic Acid Methyl Ester
Accession Number
DB01745  (EXPT01410)
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: 522.616
Monoisotopic: 522.19369078
Chemical Formula
C27H30N4O5S
InChI Key
JJLGQWCKMHPBEB-DEOSSOPVSA-N
InChI
InChI=1S/C27H30N4O5S/c1-36-27(33)20-11-13-31(14-12-20)26(32)24(16-18-5-4-8-22(15-18)25(28)29)30-37(34,35)23-10-9-19-6-2-3-7-21(19)17-23/h2-10,15,17,20,24,30H,11-14,16H2,1H3,(H3,28,29)/t24-/m0/s1
IUPAC Name
methyl 1-[(2S)-3-(3-carbamimidoylphenyl)-2-(naphthalene-2-sulfonamido)propanoyl]piperidine-4-carboxylate
SMILES
COC(=O)C1CCN(CC1)C(=O)[C@H](CC1=CC=CC(=C1)C(N)=N)NS(=O)(=O)C1=CC=C2C=CC=CC2=C1

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
446605
PubChem Substance
46505587
ChemSpider
393921
ChEMBL
CHEMBL343892
HET
FD2
PDB Entries
1k1j

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 Solubility0.0097 mg/mLALOGPS
logP2.25ALOGPS
logP1.9ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)11.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area142.65 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity151.2 m3·mol-1ChemAxon
Polarizability54.56 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.742
Blood Brain Barrier+0.5658
Caco-2 permeable-0.8377
P-glycoprotein substrateSubstrate0.8694
P-glycoprotein inhibitor INon-inhibitor0.5694
P-glycoprotein inhibitor IINon-inhibitor0.5321
Renal organic cation transporterNon-inhibitor0.653
CYP450 2C9 substrateNon-substrate0.5986
CYP450 2D6 substrateNon-substrate0.8088
CYP450 3A4 substrateNon-substrate0.5446
CYP450 1A2 substrateNon-inhibitor0.8571
CYP450 2C9 inhibitorNon-inhibitor0.7046
CYP450 2D6 inhibitorNon-inhibitor0.891
CYP450 2C19 inhibitorNon-inhibitor0.7155
CYP450 3A4 inhibitorNon-inhibitor0.6663
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8726
Ames testNon AMES toxic0.6297
CarcinogenicityNon-carcinogens0.835
BiodegradationNot ready biodegradable0.982
Rat acute toxicity2.4780 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9405
hERG inhibition (predictor II)Inhibitor0.5999
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 2-naphthalene sulfonic acids and derivatives. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group (or a derivative thereof) at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthalene sulfonic acids and derivatives
Direct Parent
2-naphthalene sulfonic acids and derivatives
Alternative Parents
2-naphthalene sulfonamides / Alpha amino acid amides / Amphetamines and derivatives / Piperidinecarboxylic acids / N-acylpiperidines / Organosulfonamides / Tertiary carboxylic acid amides / Methyl esters / Aminosulfonyl compounds / Monocarboxylic acids and derivatives
show 7 more
Substituents
2-naphthalene sulfonic acid or derivatives / Naphthalene sulfonamide / 2-naphthalene sulfonamide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / N-acyl-piperidine / Piperidinecarboxylic acid / Monocyclic benzene moiety / Piperidine
show 26 more
Molecular Framework
Aromatic heteropolycyclic 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. 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 August 02, 2019 06:54