1-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine
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Identification
- Generic Name
- 1-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine
- DrugBank Accession Number
- DB08624
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 291.372
Monoisotopic: 291.115380881 - Chemical Formula
- C13H17N5OS
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProthrombin Not Available Humans UAryl hydrocarbon receptor Not Available 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
- 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 benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazoles
- Sub Class
- Not Available
- Direct Parent
- Benzothiazoles
- Alternative Parents
- Aryl alkyl ketones / Benzenoids / Thiazoles / Heteroaromatic compounds / Alpha-amino ketones / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- 1,3-benzothiazole / Alpha-aminoketone / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Benzenoid / Carboximidamide show 15 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- MAJHCCQPIDXPAN-QMMMGPOBSA-N
- InChI
- InChI=1S/C13H17N5OS/c14-8(4-3-7-17-13(15)16)11(19)12-18-9-5-1-2-6-10(9)20-12/h1-2,5-6,8H,3-4,7,14H2,(H4,15,16,17)/t8-/m0/s1
- IUPAC Name
- N-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine
- SMILES
- N[C@@H](CCCNC(N)=N)C(=O)C1=NC2=CC=CC=C2S1
References
- Synthesis Reference
Roger J. Hopper, Budd H. Sturm, Joseph F. Geiser, "Preparation of 2-(isopropylsulfinyl)benzothiazole." U.S. Patent US4350818, issued April, 1944.
US4350818- General References
- Not Available
- External Links
- PubChem Compound
- 46937165
- PubChem Substance
- 99445095
- ChemSpider
- 26330359
- BindingDB
- 50420340
- ChEBI
- 45993
- ChEMBL
- CHEMBL2089125
- ZINC
- ZINC000053683253
- PDBe Ligand
- THZ
- PDB Entries
- 8g1w
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.13 mg/mL ALOGPS logP 0.59 ALOGPS logP 0.78 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 17.79 Chemaxon pKa (Strongest Basic) 12 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 117.88 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 88.29 m3·mol-1 Chemaxon Polarizability 30.44 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 + 0.9942 Blood Brain Barrier + 0.8558 Caco-2 permeable - 0.6795 P-glycoprotein substrate Substrate 0.5875 P-glycoprotein inhibitor I Non-inhibitor 0.9157 P-glycoprotein inhibitor II Inhibitor 0.5611 Renal organic cation transporter Inhibitor 0.6536 CYP450 2C9 substrate Non-substrate 0.8028 CYP450 2D6 substrate Non-substrate 0.7009 CYP450 3A4 substrate Non-substrate 0.7184 CYP450 1A2 substrate Inhibitor 0.6474 CYP450 2C9 inhibitor Non-inhibitor 0.8101 CYP450 2D6 inhibitor Non-inhibitor 0.616 CYP450 2C19 inhibitor Non-inhibitor 0.7545 CYP450 3A4 inhibitor Non-inhibitor 0.5133 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6243 Ames test Non AMES toxic 0.7459 Carcinogenicity Non-carcinogens 0.9624 Biodegradation Not ready biodegradable 0.9452 Rat acute toxicity 2.5910 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.953 hERG inhibition (predictor II) Non-inhibitor 0.8652
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03di-6910000000-a4c59d143831f41f2692 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-f37679539620d48a1231 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0159-0090000000-db02eca29e836b535095 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000t-0090000000-00f05f5959bd66449f69 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-044u-2960000000-75ebdc18d002cf85995a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0490000000-23b6831ad301b01cabb6 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0900000000-613b582f7caf9229b118 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]- 158.36269 predictedDeepCCS 1.0 (2019) [M+H]+ 160.72069 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.81383 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsProthrombin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing. Thrombin triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL8/CXCL8, in endothelial cells (PubMed:30568593, PubMed:9780208)
- Specific Function
- calcium ion binding
- Gene Name
- F2
- Uniprot ID
- P00734
- Uniprot Name
- Prothrombin
- Molecular Weight
- 70036.295 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]
2. DetailsAryl hydrocarbon receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ligand-activated transcription factor that enables cells to adapt to changing conditions by sensing compounds from the environment, diet, microbiome and cellular metabolism, and which plays important roles in development, immunity and cancer (PubMed:23275542, PubMed:30373764, PubMed:32818467, PubMed:7961644). Upon ligand binding, translocates into the nucleus, where it heterodimerizes with ARNT and induces transcription by binding to xenobiotic response elements (XRE) (PubMed:23275542, PubMed:30373764, PubMed:7961644). Regulates a variety of biological processes, including angiogenesis, hematopoiesis, drug and lipid metabolism, cell motility and immune modulation (PubMed:12213388). Xenobiotics can act as ligands: upon xenobiotic-binding, activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene) (PubMed:7961644). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons (PubMed:34521881, PubMed:7961644). Next to xenobiotics, natural ligands derived from plants, microbiota, and endogenous metabolism are potent AHR agonists (PubMed:18076143). Tryptophan (Trp) derivatives constitute an important class of endogenous AHR ligands (PubMed:32818467, PubMed:32866000). Acts as a negative regulator of anti-tumor immunity: indoles and kynurenic acid generated by Trp catabolism act as ligand and activate AHR, thereby promoting AHR-driven cancer cell motility and suppressing adaptive immunity (PubMed:32818467). Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1 (PubMed:28602820). Inhibits PER1 by repressing the CLOCK-BMAL1 heterodimer mediated transcriptional activation of PER1 (PubMed:28602820). The heterodimer ARNT:AHR binds to core DNA sequence 5'-TGCGTG-3' within the dioxin response element (DRE) of target gene promoters and activates their transcription (PubMed:28602820)
- Specific Function
- cis-regulatory region sequence-specific DNA binding
- Gene Name
- AHR
- Uniprot ID
- P35869
- Uniprot Name
- Aryl hydrocarbon receptor
- Molecular Weight
- 96146.705 Da
References
- Noguerol TN, Boronat S, Casado M, Raldua D, Barcelo D, Pina B: Evaluating the interactions of vertebrate receptors with persistent pollutants and antifouling pesticides using recombinant yeast assays. Anal Bioanal Chem. 2006 Jul;385(6):1012-9. Epub 2006 May 17. [Article]
Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52