NAV

RWJ-56423

Identification

Generic Name
RWJ-56423
DrugBank Accession Number
DB02812
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 446.523
Monoisotopic: 446.17362404
Chemical Formula
C20H26N6O4S
Synonyms
  • (2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
External IDs
  • RWJ-56423
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTrypsin-1
inhibitor
Humans
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
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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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Benzothiazoles / Aryl alkyl ketones / N-acylpyrrolidines / Pyrrolidinecarboxamides / Benzenoids / Heteroaromatic compounds / Acetamides / Tertiary carboxylic acid amides / Thiazoles
show 8 more
Substituents
1,3-benzothiazole / Acetamide / Alcohol / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Benzenoid
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, guanidines, pyrrolidinecarboxamide, L-proline derivative, N-acylpyrrolidine (CHEBI:40491)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VXDAVYUFYPFGDX-SNPRPXQTSA-N
InChI
InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15+/m1/s1
IUPAC Name
(2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
SMILES
[H]N([H])C(=NCCC[C@H](N([H])C(=O)[C@@H]1C[C@@H](O)CN1C(C)=O)C(=O)C1=NC2=CC=CC=C2S1)N([H])[H]

References

General References
Not Available
PubChem Compound
5287596
PubChem Substance
46509114
ChemSpider
4449928
BindingDB
50228764
ChEMBL
CHEMBL256892
ZINC
ZINC000003916454
PDBe Ligand
ABB
PDB Entries
1nc6

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 Solubility0.144 mg/mLALOGPS
logP-0.01ALOGPS
logP-1.1Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.27Chemaxon
pKa (Strongest Basic)11.05Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area164 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity113.74 m3·mol-1Chemaxon
Polarizability46.34 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9003
Blood Brain Barrier-0.886
Caco-2 permeable-0.804
P-glycoprotein substrateSubstrate0.8239
P-glycoprotein inhibitor INon-inhibitor0.9212
P-glycoprotein inhibitor IINon-inhibitor0.8726
Renal organic cation transporterNon-inhibitor0.6401
CYP450 2C9 substrateNon-substrate0.702
CYP450 2D6 substrateNon-substrate0.7862
CYP450 3A4 substrateNon-substrate0.54
CYP450 1A2 substrateNon-inhibitor0.7214
CYP450 2C9 inhibitorNon-inhibitor0.7349
CYP450 2D6 inhibitorNon-inhibitor0.888
CYP450 2C19 inhibitorNon-inhibitor0.6851
CYP450 3A4 inhibitorNon-inhibitor0.6974
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7459
Ames testNon AMES toxic0.6824
CarcinogenicityNon-carcinogens0.8778
BiodegradationNot ready biodegradable0.9723
Rat acute toxicity2.5098 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9665
hERG inhibition (predictor II)Non-inhibitor0.6539
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/MSsplash10-004j-0241900000-3e944aabf7cd8b5e37df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0109200000-1b9d4cdaca74297f07cb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2629600000-cb5efaf7e8c774f970e6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-5425900000-caa529bee7f494b1a80e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9703200000-76afefaddcc4f2eb7a59
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-2932100000-93646ea2338a8af0ea95
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.17876
predicted
DeepCCS 1.0 (2019)
[M+H]+194.27238
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.1849
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Trypsin-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Costanzo MJ, Yabut SC, Almond HR Jr, Andrade-Gordon P, Corcoran TW, De Garavilla L, Kauffman JA, Abraham WM, Recacha R, Chattopadhyay D, Maryanoff BE: Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone. J Med Chem. 2003 Aug 28;46(18):3865-76. doi: 10.1021/jm030050p. [Article]

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