RWJ-56423
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Identification
- Generic Name
- RWJ-56423
- DrugBank Accession Number
- DB02812
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- 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
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTrypsin-1 inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 5287596
- PubChem Substance
- 46509114
- ChemSpider
- 4449928
- BindingDB
- 50228764
- ChEMBL
- CHEMBL256892
- ZINC
- ZINC000003916454
- PDBe Ligand
- ABB
- PDB Entries
- 1nc6
Clinical Trials
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
Property Value Source Water Solubility 0.144 mg/mL ALOGPS logP -0.01 ALOGPS logP -1.1 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 12.27 Chemaxon pKa (Strongest Basic) 11.05 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 164 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 113.74 m3·mol-1 Chemaxon Polarizability 46.34 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9003 Blood Brain Barrier - 0.886 Caco-2 permeable - 0.804 P-glycoprotein substrate Substrate 0.8239 P-glycoprotein inhibitor I Non-inhibitor 0.9212 P-glycoprotein inhibitor II Non-inhibitor 0.8726 Renal organic cation transporter Non-inhibitor 0.6401 CYP450 2C9 substrate Non-substrate 0.702 CYP450 2D6 substrate Non-substrate 0.7862 CYP450 3A4 substrate Non-substrate 0.54 CYP450 1A2 substrate Non-inhibitor 0.7214 CYP450 2C9 inhibitor Non-inhibitor 0.7349 CYP450 2D6 inhibitor Non-inhibitor 0.888 CYP450 2C19 inhibitor Non-inhibitor 0.6851 CYP450 3A4 inhibitor Non-inhibitor 0.6974 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7459 Ames test Non AMES toxic 0.6824 Carcinogenicity Non-carcinogens 0.8778 Biodegradation Not ready biodegradable 0.9723 Rat acute toxicity 2.5098 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9665 hERG inhibition (predictor II) Non-inhibitor 0.6539
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0241900000-3e944aabf7cd8b5e37df Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0109200000-1b9d4cdaca74297f07cb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-2629600000-cb5efaf7e8c774f970e6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-5425900000-caa529bee7f494b1a80e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-9703200000-76afefaddcc4f2eb7a59 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01p9-2932100000-93646ea2338a8af0ea95 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.17876 predictedDeepCCS 1.0 (2019) [M+H]+ 194.27238 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.1849 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTrypsin-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
- 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