[N-[N-(4-Methoxy-2,3,6-trimethylphenylsulfonyl)-L-aspartyl]-D-(4-amidino-phenylalanyl)]-piperidine

Identification

Generic Name
[N-[N-(4-Methoxy-2,3,6-trimethylphenylsulfonyl)-L-aspartyl]-D-(4-amidino-phenylalanyl)]-piperidine
DrugBank Accession Number
DB03081
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 601.714
Monoisotopic: 601.257019317
Chemical Formula
C29H39N5O7S
Synonyms
Not Available
External IDs
  • CRC200
  • RC-220

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Aspartic acid and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Benzenesulfonamides / N-acylpiperidines / Benzenesulfonyl compounds / Phenoxy compounds / Methoxybenzenes / Anisoles
show 15 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amidine / Aminosulfonyl compound / Amphetamine or derivatives / Anisole / Aromatic heteromonocyclic compound / Aspartic acid or derivatives
show 37 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, carboxamidine, L-asparagine derivative, piperidones (CHEBI:41374)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
146663-95-8
InChI Key
ZOXOKTJHZSUHRJ-XZOQPEGZSA-N
InChI
InChI=1S/C29H39N5O7S/c1-17-14-24(41-4)18(2)19(3)26(17)42(39,40)33-22(16-25(35)36)28(37)32-23(29(38)34-12-6-5-7-13-34)15-20-8-10-21(11-9-20)27(30)31/h8-11,14,22-23,33H,5-7,12-13,15-16H2,1-4H3,(H3,30,31)(H,32,37)(H,35,36)/t22-,23+/m0/s1
IUPAC Name
(3S)-3-{[(2R)-3-(4-carbamimidoylphenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl]carbamoyl}-3-(4-methoxy-2,3,6-trimethylbenzenesulfonamido)propanoic acid
SMILES
COC1=C(C)C(C)=C(C(C)=C1)S(=O)(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC1=CC=C(C=C1)C(N)=N)C(=O)N1CCCCC1

References

General References
Not Available
PubChem Compound
177837
PubChem Substance
46508948
ChemSpider
154815
ChEMBL
CHEMBL1231689
ZINC
ZINC000003807259
PDBe Ligand
CCR
PDB Entries
1k1n / 1ypk

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0194 mg/mLALOGPS
logP0.18ALOGPS
logP0.48ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)11.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area191.98 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity168.66 m3·mol-1ChemAxon
Polarizability60.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9135
Blood Brain Barrier-0.894
Caco-2 permeable-0.7283
P-glycoprotein substrateSubstrate0.8722
P-glycoprotein inhibitor INon-inhibitor0.5298
P-glycoprotein inhibitor IINon-inhibitor0.7108
Renal organic cation transporterNon-inhibitor0.7988
CYP450 2C9 substrateNon-substrate0.537
CYP450 2D6 substrateNon-substrate0.787
CYP450 3A4 substrateSubstrate0.5483
CYP450 1A2 substrateNon-inhibitor0.8427
CYP450 2C9 inhibitorNon-inhibitor0.7527
CYP450 2D6 inhibitorNon-inhibitor0.9027
CYP450 2C19 inhibitorNon-inhibitor0.7783
CYP450 3A4 inhibitorNon-inhibitor0.6681
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9527
Ames testNon AMES toxic0.6284
CarcinogenicityNon-carcinogens0.7672
BiodegradationNot ready biodegradable0.9381
Rat acute toxicity2.4430 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9009
hERG inhibition (predictor II)Inhibitor0.7787
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

Targets

Drugtargets
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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. [Article]
  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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52