2-[3-(5-Mercapto-[1,3,4]thiadiazol-2-yl)-ureido]-N-methyl-3-phenyl-propionamide
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Identification
- Generic Name
- 2-[3-(5-Mercapto-[1,3,4]thiadiazol-2-yl)-ureido]-N-methyl-3-phenyl-propionamide
- DrugBank Accession Number
- DB07390
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 337.421
Monoisotopic: 337.066716129 - Chemical Formula
- C13H15N5O2S2
- Synonyms
- Not Available
- External IDs
- PNU-107859
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism A72 kDa type IV collagenase inhibitorHumans AStromelysin-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
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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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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
- Phenylalanine and derivatives
- Alternative Parents
- N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / 1,3,4-thiadiazol-2-ylureas / Fatty amides / Heteroaromatic compounds / Ureas / Secondary carboxylic acid amides / Azacyclic compounds / Organosulfur compounds show 5 more
- Substituents
- 1,3,4-thiadiazol-2-ylurea / Alpha-amino acid amide / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group show 18 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- ureas, thiadiazoles, L-phenylalanine derivative (CHEBI:40873)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- RKWXKADYTDWZIJ-VIFPVBQESA-N
- InChI
- InChI=1S/C13H15N5O2S2/c1-14-10(19)9(7-8-5-3-2-4-6-8)15-11(20)16-12-17-18-13(21)22-12/h2-6,9H,7H2,1H3,(H,14,19)(H,18,21)(H2,15,16,17,20)/t9-/m0/s1
- IUPAC Name
- (2S)-N-methyl-3-phenyl-2-{[(5-sulfanylidene-4,5-dihydro-1,3,4-thiadiazol-2-yl)carbamoyl]amino}propanamide
- SMILES
- CNC(=O)[C@H](CC1=CC=CC=C1)NC(=O)NC1=NNC(=S)S1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 4369084
- PubChem Substance
- 99443861
- ChemSpider
- 3571806
- BindingDB
- 50241372
- ChEMBL
- CHEMBL249847
- ZINC
- ZINC000006379443
- PDBe Ligand
- ATT
- PDB Entries
- 3usn
Clinical Trials
- Clinical Trials
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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 0.0646 mg/mL ALOGPS logP 1.39 ALOGPS logP 1.81 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 7.23 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 94.62 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 89.38 m3·mol-1 Chemaxon Polarizability 33.91 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5482 Blood Brain Barrier + 0.921 Caco-2 permeable - 0.6167 P-glycoprotein substrate Non-substrate 0.58 P-glycoprotein inhibitor I Non-inhibitor 0.7724 P-glycoprotein inhibitor II Non-inhibitor 0.9433 Renal organic cation transporter Non-inhibitor 0.8871 CYP450 2C9 substrate Non-substrate 0.6903 CYP450 2D6 substrate Non-substrate 0.8093 CYP450 3A4 substrate Non-substrate 0.6609 CYP450 1A2 substrate Non-inhibitor 0.6105 CYP450 2C9 inhibitor Inhibitor 0.5345 CYP450 2D6 inhibitor Non-inhibitor 0.92 CYP450 2C19 inhibitor Non-inhibitor 0.5319 CYP450 3A4 inhibitor Non-inhibitor 0.8088 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6315 Ames test Non AMES toxic 0.6681 Carcinogenicity Non-carcinogens 0.8881 Biodegradation Not ready biodegradable 0.9604 Rat acute toxicity 2.2821 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9719 hERG inhibition (predictor II) Non-inhibitor 0.7662
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-6932000000-0fa239b4cca419dbed33 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002r-0659000000-30d4d2ec477101b390e0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0aos-2914000000-fd3c32759b26e8c6f18a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0910000000-6de372899d798a68203f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-5920000000-e3111960e01d14b92c97 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-06ec-3900000000-db07413be4b521cdd4f4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0aor-9800000000-caba34926c4845ea2881 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]- 167.07109 predictedDeepCCS 1.0 (2019) [M+H]+ 169.4291 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.72615 predictedDeepCCS 1.0 (2019)
Targets
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1. Details72 kDa type IV collagenase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rupture. As well as degrading extracellular matrix proteins, can also act on several nonmatrix proteins such as big endothelial 1 and beta-type CGRP promoting vasoconstriction. Also cleaves KISS at a Gly-|-Leu bond. Appears to have a role in myocardial cell death pathways. Contributes to myocardial oxidative stress by regulating the activity of GSK3beta. Cleaves GSK3beta in vitro. Involved in the formation of the fibrovascular tissues in association with MMP14
- Specific Function
- Endopeptidase activity
- Gene Name
- MMP2
- Uniprot ID
- P08253
- Uniprot Name
- 72 kDa type IV collagenase
- Molecular Weight
- 73881.695 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsStromelysin-1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metalloproteinase with a rather broad substrate specificity that can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates different molecules including growth factors, plasminogen or other matrix metalloproteinases such as MMP9 (PubMed:11029580, PubMed:1371271). Once released into the extracellular matrix (ECM), the inactive pro-enzyme is activated by the plasmin cascade signaling pathway (PubMed:2383557). Acts also intracellularly (PubMed:22265821). For example, in dopaminergic neurons, gets activated by the serine protease HTRA2 upon stress and plays a pivotal role in DA neuronal degeneration by mediating microglial activation and alpha-synuclein/SNCA cleavage (PubMed:21330369). In addition, plays a role in immune response and possesses antiviral activity against various viruses such as vesicular stomatitis virus, influenza A virus (H1N1) and human herpes virus 1 (PubMed:35940311). Mechanistically, translocates from the cytoplasm into the cell nucleus upon virus infection to influence NF-kappa-B activities (PubMed:35940311)
- Specific Function
- Endopeptidase activity
- Gene Name
- MMP3
- Uniprot ID
- P08254
- Uniprot Name
- Stromelysin-1
- Molecular Weight
- 53976.84 Da
References
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:21 / Updated at August 26, 2024 19:22