N-Alpha-(2-Naphthylsulfonyl)-N-(3-Amidino-L-Phenylalaninyl)-D-Pipecolinic Acid

Identification

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Name
N-Alpha-(2-Naphthylsulfonyl)-N-(3-Amidino-L-Phenylalaninyl)-D-Pipecolinic Acid
Accession Number
DB04238  (EXPT01409)
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: 508.589
Monoisotopic: 508.178040716
Chemical Formula
C26H28N4O5S
InChI Key
GNANSBQAIRJZPA-XZOQPEGZSA-N
InChI
InChI=1S/C26H28N4O5S/c27-24(28)20-9-5-6-17(14-20)15-22(25(31)30-13-4-3-10-23(30)26(32)33)29-36(34,35)21-12-11-18-7-1-2-8-19(18)16-21/h1-2,5-9,11-12,14,16,22-23,29H,3-4,10,13,15H2,(H3,27,28)(H,32,33)/t22-,23+/m0/s1
IUPAC Name
(2R)-1-[(2S)-3-(3-carbamimidoylphenyl)-2-(naphthalene-2-sulfonamido)propanoyl]piperidine-2-carboxylic acid
SMILES
[H][C@@](CC1=CC(=CC=C1)C(N)=N)(NS(=O)(=O)C1=CC2=CC=CC=C2C=C1)C(=O)N1CCCC[C@]1([H])C(O)=O

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
446604
PubChem Substance
46506342
ChemSpider
393920
ChEMBL
CHEMBL1161253
HET
FD1
PDB Entries
1k1i

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 Solubility0.0137 mg/mLALOGPS
logP0.9ALOGPS
logP0.95ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)11.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area153.65 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity146.02 m3·mol-1ChemAxon
Polarizability51.78 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7113
Blood Brain Barrier-0.638
Caco-2 permeable-0.8361
P-glycoprotein substrateSubstrate0.7085
P-glycoprotein inhibitor INon-inhibitor0.8257
P-glycoprotein inhibitor IINon-inhibitor0.6488
Renal organic cation transporterNon-inhibitor0.7715
CYP450 2C9 substrateNon-substrate0.6196
CYP450 2D6 substrateNon-substrate0.8402
CYP450 3A4 substrateNon-substrate0.6215
CYP450 1A2 substrateNon-inhibitor0.8833
CYP450 2C9 inhibitorNon-inhibitor0.7282
CYP450 2D6 inhibitorNon-inhibitor0.8934
CYP450 2C19 inhibitorNon-inhibitor0.7831
CYP450 3A4 inhibitorNon-inhibitor0.8304
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9769
Ames testNon AMES toxic0.6459
CarcinogenicityNon-carcinogens0.8313
BiodegradationNot ready biodegradable0.9775
Rat acute toxicity2.2912 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.6471
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
2-naphthalene sulfonamides / 2-naphthalene sulfonic acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Piperidinecarboxylic acids / N-acylpiperidines / Organosulfonamides / Tertiary carboxylic acid amides / Aminosulfonyl compounds / Monocarboxylic acids and derivatives
show 8 more
Substituents
Alpha-dipeptide / Naphthalene sulfonic acid or derivatives / 2-naphthalene sulfonic acid or derivatives / Naphthalene sulfonamide / 2-naphthalene sulfonamide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Naphthalene / N-acyl-piperidine
show 28 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 June 04, 2019 06:03